Caldwell P. People Ops - Lessons in Culture and Leadership..Building Startups 2023

People Ops
Lessons in Culture and

Leadership From Building Startups
―
Patrick Caldwell
People Ops
Lessons in Culture and
Leadership From Building
Startups
Patrick Caldwell
People Ops: Lessons in Culture and Leadership From Building Startups
Patrick Caldwell
London, UK
ISBN-13 (pbk): 978-1-4842-9818-3 ISBN-13 (electronic): 978-1-4842-9819-0

https://doi.org/10.1007/978-1-4842-9819-0
Copyright © 2023 by Patrick Caldwell

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Table of Contents
About the Author��vii
Preface��ix
Chapter 1: Building from Scratch��1

Ground Your Decision-Making��3
Simple Is Sexy��5
Done > Perfect��6
Self-Service FTW��8
Decision by Committee Sucks��10
Beware the Magpies��12
Your People Strategy Is Your Business Strategy��14
Summary��15
Chapter 2: Leadership��17
Red Flag 1: Lack of Leadership��18
Red Flag 2: The Wrong Leaders��21
Red Flag 3: Accidental Leaders��22
Not Everyone Wants to, or Should, Be a Leader��23
The Psychological Safety of Leaders��24
If Difficult Conversations Don’t Affect You, You Shouldn’t Be Having Them��26
Sometimes to Show You Care, You Need to Show Your Teeth��28
Summary��29
iii
Table of Contents
Chapter 3: Culture��31
Culture Is Not Free Beer, Fruit, and a PlayStation��31
Culture Contribution or Culture Fit��32
What Does Autonomy Look Like for You?��35
Process: The Enemy or the Hero?��37
Cut Only When Is Absolutely Necessary to Survive��39
Find a Common Language��43
Getting Past the Values Fluff��45
Summary��47
Chapter 4: Inclusion��49
Inclusion > Diversity��50
Pitch at 80%��53
Be Judged by Your Actions, Not Your Intentions��54
Get Under the Skin of Your Gender Pay Gap��55
The Myth of Removing Bias��60
Summary��61
Chapter 5: Recruitment��63
Respond to Every Single Job Applicant As Though Your Brand Depends on It��64
Start with Your Best Offer and Don’t Budge��66
Your Candidate Experience Is As Important As Your Customer Experience��69
Turn the Tables��71
Don’t Join This Company If…��71
The Candidate Was Great! I’d Like to Meet a Few More Though��72
Summary��74
iv
Table of Contents
Chapter 6: Reward��77
Design for the 99%��77
Pay Transparency��82
The “Pay Me More or I’ll Leave” Ultimatum��88
The Law Is the Floor��91
All Benefits Are for Day 1��92
You Probably Won’t Retire Early Because of Equity��93
Minimum Leave, Not Unlimited Leave��99
Summary��100
Chapter 7: Learning��103
Water Your Plants��103
Learning Is About Experiences, Not Just Knowledge��107
The “Best” Career Advice I Ever Received��109
Approach with Planning: Peer Feedback��113
The Perfect Resignation: When the Time Is Simply Right��115
Summary��116
Chapter 8: Performance��117
The Trinity: What, How, Where?��117
I Messed Up OKRs, Twice!��120
People Outgrow Startups; Startups Outgrow People��122
If I Hear “Hire Slow, Fire Fast” One More Time…��125
The Death of Performance Reviews?��127
Summary��132
v
Table of Contents
Chapter 9: Remote Working��135

The Covid-19 Acceleration��135
Remote Work Is Uncovering Our Dirty Laundry��136
Know the Difference Between Flexible and Remote Work��139
The Remote Manager��141
Burnout Is Our New Thanos��143
Summary��144
Chapter 10: Your Career��147

Know the Difference Between Who You Are and What You Do��147
Be Clear on What Your Role Is and What It Isn’t��149
“I Don’t Know”��150
Find Your Outlet��151
Be Ruthless with Your Time��153
Everyone Is a People Expert��156
It’s Great to Experience a Truly Shit Company at Least Once��158
Scaling Part 1: Keep Your Team As Small As Possible��159
Scaling Part 2: Make Yourself Redundant��163
Summary��164
Chapter 11: TL;DR��167

Too Long; Didn’t Read: A Summary of Text That Was Too Lengthy��167
Index��179
vi
About the Author
Patrick Caldwell is a multi-startup People
& Operational leader with experience in
leadership teams and boards across Australia,
the United States, and Europe. Pat is currently
building out the first people and culture
strategy as the Chief People Officer at Send,
an InsurTech software company in the UK,
and also serves as a Non-Executive Director
on the board of ImpactEd, an EdTech scale-up
helping purpose-driven schools, educational
institutions, and partners with high-quality evidence and evaluation to
improve outcomes for young people. Hailing from the coal mining industry
in Australia, Patrick was formerly the COO at FundApps, an award-winning
B Corporation, and the VP People & Operations at Metomic, an innovative
cybersecurity technology startup.
vii
Preface
“Patrick should consider if HR is right for him. He seems frustrated most
of the time.”
My first reaction was “pfft, whatever” to this gem from a 360
assessment. I wouldn’t have been so frustrated if I felt like we were actually
having a positive impact on people. But I wasn’t. I was churning through
spreadsheets, lists of policies, and the odd disciplinary that made up my
days in what was jokingly (not really) known by a supervisor as the Human
Remains department. Honorable mention to his second favorite name, the
Hardly Relevant department.
This isn’t an exception. This is still what the vast majority of people
experience and come to expect from their HR department. The people
you speak to when something is wrong, or better put, the people you hope
to not need to speak to. Despite years of incremental change, we haven’t
yet shaken the compliance-driven, “on the employer’s side,” back-office
shadow that we’ve cast into businesses. And maybe we never will, at least
completely.
But this isn’t a book to bash HR, as therapeutic as part of me might find
that. It’s a book about what HR is becoming and the transformation of how
we think about people and culture. We’re part of a generation of teams,
leaders, and businesses demanding an entirely new breed of capability
around people and culture. We’re becoming People teams, relentlessly
focused on how we engage, develop, empower, and recognize people
and how our obsession with culture and the people experience can drive
businesses to success.
ix
Preface
I fundamentally believe in the coming years we’ll see People functions

entirely replacing what we’ve come to associate with traditional HR. Some
of that work will still need to be done, but it won’t be the purpose of the
People team, or how we add the most value to a business. We’ll no longer
be just partners and advisors to a business either. We’ll be in the business
and working on the business. We’ll treat our recruitment and onboarding
experience with the same focus, care, and attention that we do our sales
pipeline. We’ll be fully in sync with our people and looking for ways to
increase their success and nurture relationships in the same way our
customer success teams do. We’ll be working cross-functionally to design
and iterate our work in the same way we expect our Product teams to. And
we’ll be armed with the same tools and data insights that we’ve come to
expect from our technology teams.
My first experience with what is now demanded from People teams
came in startups. It’s not exclusive to startups, and they can receive a
disproportionate level of recognition around innovation in the people
space simply because they’re not the stereotype of a large business (shout
out to the People innovators in big businesses too!). Startups are, however,
a really insightful test for what will be in the years ahead.
In startups, every founding and leadership team experiencing growth
will at some point make a decision to introduce a People capability into
their team. There’s no baggage with this decision and usually no existing
team, processes, or ways of working that influence what a People team
can be in their business. Startups allow us to see how leaders answer this
question: When you can build it from scratch, what do you aspire for the
People team to be?
As I transitioned from the world of HR to the world of People, I also
met some truly incredible folks in both People roles and elsewhere in the
business, who have helped shape my perspectives and work for how we
engage, develop, empower, and recognize people. As passionate as I may
be about both people and culture, I’ll never be an expert and I don’t think
x
Preface
that’s possible anyway. We’re constantly learning, adapting, and changing

how we think about people, and keeping up with that by itself, let alone
in high-growth startups, is a thrilling challenge. It also means I’ve had to
learn things the right way – by doing them. Sometimes they worked, and a
lot of the time they didn’t and I had to iterate my thinking and approach.
As quite a reflective person, I also found myself making mental notes
along the way. Things I observed, suggested, struggled with, worked on,
screwed up, or smashed out of the park all made their way into my mental
notes in the hope they might prove useful the next time I was faced with
a similar scenario. Over time, these mental notes became written notes,
throughout a myriad of notebooks, journals, and eventually a Notion page
of stuff I didn’t want to forget.
What you’ll find in this book are those mental notes I made along the
way. This is not a book bursting with management theory and frameworks,
rather a collection of stories, personal principles, and lessons learned.
It’s grounded in my experience and the experience of those I’ve been
fortunate enough to work with. I wrote these mental notes for me, but I’m
sharing with you in the same way I might if we were chatting at the pub.
And while every business is different, I hope there is something in here for
everyone at whatever stage you are.
If you are like me and have a short attention span, or don’t read books
cover to cover, I’d highly recommend starting with Chapter 11.
—Pat
P.S. It turns out HR was not right for me. But I think People Ops might
just be.
xi
CHAPTER 1
Building from Scratch

If you’ve joined a startup, or even interviewed at one, you’ll likely have
been sold the utopia of building on a blank canvas. That we have no
processes in place, no playbook to make our success repeatable, no idea
what we’re even doing. OK, maybe not that last one, but I’ll come on to
that later and why it wouldn’t be such a bad thing to tell people up front.
As incredible and liberating as a blank canvas sounds, it’s a myth.
Don’t get me wrong, I still get warm fuzzies anytime I think about building
things from scratch in a startup. But unless you are a founder starting a
company, there is no such thing as a blank canvas. The canvas is already
sprawled with paint around culture and leadership – existing beliefs,
norms, ways of working, expectations, personalities, conflicts, highs and
lows of everything that has happened before you showed up. The paint
might not look like a work of art, but it’s already there whether you like
it or not.
There are an endless number of ways that paint can be sprawled across
the canvas, but here’s a selection of some of my favorites from my early
days within various startups:
• The hiring engine that takes place through “who do we

know who could do this?” rather than “how will we find
someone who will be awesome at this?”
• Having no onboarding process because great people

onboard themselves.
© Patrick Caldwell 2023 1

P. Caldwell, People Ops, https://doi.org/10.1007/978-1-4842-9819-0_1
Chapter 1 Building from Scratch
• The employee who earns half of what they are worth

on the market but operates under the belief that in five
years the startup will be a unicorn and they can cash
out on their equity and retire early.
• Justifying the lack of job descriptions with the fact

people wear lots of hats in a startup.
• The founder who believes every employee who joins

should be as deeply invested and committed to the
cause as they are.
• The promotion of a mid-level individual contributor

to CxO after six months because they know the
product well.
• And, my favorite one, believing that they have a

learning culture because a few developers went to a
conference last year.
Sound familiar?
At the start of my time with every high-growth startup I’ve joined,
there’s a period for several weeks when I try to actively observe the paint
on the canvas. This is harder than it sounds, but the benefit of being so new
to a company is that you’re viewing that canvas from the perfect angle. You
haven’t been involved at all in painting it, so you have that beautiful mix
of objectivity and curiosity. In a short while, that objectivity is mostly gone
and you’re now also painting the canvas and getting stuff done.
For the next few months, the key to surviving a startup is to find
the balance on getting stuff done today and keeping one eye on what’s
coming next. You need to be tactical enough to stay off the “not right for
this stage of our growth” list, but thoughtful and strategic enough to be on
2
the “grow with us” list. And so here seems the logical place to start sharing
some of my musings with the hope you might make at least one less
mistake than I have.
Ground Your Decision-Making

I often wish managing people and building teams was more black and
white. Instead, we’re faced with various shades of gray and expected to
navigate through that with ease. Good judgment is important, but by itself
judgment can be too easily confused with an opinion. What makes this
easier is how you anchor your judgment in relevant data and information.
One of the frogs I try to eat very early in my time at any startup is
compensation. If the startup is bootstrapped, we have to operate within
very tight cash restrictions and that means making educated and informed
judgments on where we get the most bang for our buck when it comes to
compensation. If the startup is backed, the same principle should apply
too but with a wee bit more flexibility if the pockets you have are deeper.
Compensation is deeply emotional. If you’re in the tech industry, it’s
going to be the biggest area of your spend. If you’re in another industry,
it’ll be one of the top three areas of spend. So getting it right is critical.
But that’s just the company side of compensation. For us as individuals,
we don’t really care how much of the P&L is dedicated to compensation.
We just care about how much we get and whether it meets a few criteria
around right and wrong:
• Expectations: Does it seem right based on what

I’m expected to do? I’ve lost track of the number of
negotiations where the basis of the ask is their gut feel
on whether the package seems like it fits with the role.
3
• Lifestyle: There are two points to this to be mindful of:

What was I earning previously and is this the same or
better? And what sort of lifestyle am I trying to live or
uphold? A software engineer from a big tech company
on $300k per year with a lifestyle around this is going to
find your offer of $200k to be unwelcome regardless of
how much data exists.
• Status and sense of worth: Never underestimate this. It’s

normal, human, and common to find a sense of worth
in our salary. For some people, it’s inconsequential. For
others, it’s everything!
• Fairness: I’ve framed most of the preceding criteria

in the context of a new starter considering their
compensation, but the fairness criterion is one of the
most vital considerations for the existing team. If you’ve
been in your role for a year, perhaps you had a small
bump recently, and you find out a new team member
doing the same role has joined and has a higher pay
than you, you’re likely going to be pretty down about
that regardless of their background.
I used to believe I could architect a perfect, data-backed model for
startup compensation. I’ve tried a few times, and each time I ended up
realizing something really important. Everyone supports a data-driven
approach to compensation, until the data conflicts with what they want to
be paid.
Over time, I started to accept that a bit of art in compensation was
never a bad thing – 80% science, 20% art. Put principles around how
compensation is determined and use data and benchmarks to inform that.
Use compa ratios or compensation ranges to build fairness into routines.
And, most importantly, communicate transparently with the team and
external candidates how compensation is set and reviewed.
4
Not everyone will be a fan of this. Frankly, it’s usually the people who
benefited from what the system used to be. But achieving 100% support
is not the point here. You’re optimizing for something that creates fair,
equitable, and consistent compensation outcomes and sometimes that
means some tough reality checks for people. The key here is that having
your decision-making grounded in something objective, with a small
amount of flexibility to cater for the realities of such an emotional and
complex topic.
Simple Is Sexy
There is a certain urgency that people challenges tend to instill in a startup.
Unfortunately, urgency has a knack for distorting decision-making toward
the short term and that often comes back to bite you in the ass.
Let’s consider recruitment. You need to grow fast! You feel the pressure
from hiring managers. You find an amazing candidate who at the offer
stage wants to negotiate some bespoke terms in their contract like a
guaranteed bonus or a higher notice period. Maybe a different health
insurance package or some nuance in their commission plan. Agreeing to
these sorts of changes is often made out to be insignificant. A small price to
pay to land a candidate and fill that role you’ve been trying to for ages.
Let’s now add double- or triple-digit growth on top of that. Your team
of 80 is now 240 and you have the complexity of individual terms and
conditions to be administered on a much larger scale. It means the teams
and infrastructure needed to administer that complexity grow with it. And
don’t forget that people talk. So Joe will find out eventually that he has a
less attractive commission structure than Sally, and Sally will learn that
Kate has a benefit that you asked for but were told you couldn’t have.
You get the point. Simple is sexy. And grossly underrated.
5
When it comes to employment terms in a growing company, there is

a lot to be said for simple, consistently applied terms across the broadest
remit possible – that includes notice periods, leave entitlements, benefits,
commission plans, bonuses, and anything else you might expect to be
negotiated into an employment contract. There will always be some
variability due to regional differences if the team grows globally, so if you
have the luxury to join a company early before a period of hyper-growth,
consider what the default offering looks like across as many employment
terms as possible and don’t budge.
Done > Perfect

Outside of startups, there’s a fairly common way of working in the People
space. You table ideas and put together proposals with hope that senior
leaders will approve it. You write extensive business cases justifying
ROI and book meetings with key stakeholders looking for feedback and
ambassadorship. You’ll have a communication strategy in place which in
turn will generate communication and implementation plans. And finally,
you’ll have a feedback and review cycle on your initiative to remind senior
leaders of how well it’s performing.
I used to work in this way. For years. I know of a number of people who
have built their careers around their ability to thoroughly and methodically
plan for every circumstance and they rarely spend time actually executing.
Then I ended up in startups where most of that work is more
insignificant than I cared to recognize. I’m not suggesting engaging
stakeholders and being thoughtful about strategy isn’t important, just that
the difference between a good initiative and a near-perfect initiative is of
very little consequence in a startup. It’s likely why we’ve ended up with so
many “get shit done” company values that prioritize execution and pace.
6
In startups, having something in place that’s about 80% done is of

far more value to the company than waiting weeks or months until it’s
perfectly complete. The more potent realization for me was that anything
you build you’ll likely need to upgrade or replace a number of times
anyway as the company grows. After all, if you’re doubling headcount year
on year, what you build in year one for 100 people is likely going to need a
lot of iterating to still be effective for 400 people in year two.
There is undoubtedly a long line of “but what about this?”
considerations. The goal of prioritizing done over perfect is not about
neglecting some of the key steps to change, in particular around
communication, engagement, and influencing leaders. The goal is to get
the initiative to a point where it’s solving a problem or delivering value,
and then approaching it with a mindset to iterate and improve once it’s in
place. Here are a few things to clarify early to set this up for success:
1. Is the initiative aligned with what the company

is trying to achieve? There are 10,000 things we
probably could be doing. Find the two to three most
important ones that help the company achieve
its goals. This will speed up how you engage and
influence.
2. How will you communicate the initiative in a few
different ways? Skip the vanity social media posts
and five-slide cascading communication plan. The
key here is to answer the question: How will every
team know about this? In many startups, a combo
of async messaging tools, all-hands and stand-up
routines, intranet pages, and a bit of rinsing and
repeating will do the trick.
7
3. Do you have a rough idea what success looks like?

This needn’t be a set of objectives and a pyramid of
key results. What’s the most important thing you’re
solving for and how will you know you’ve done
that? Focus on that when you’re communicating to
leaders and the team.
4. How will you set expectations? In a number

of startups, I’ve used the symbol of a naming
convention to many of the bigger initiatives.
Parental Leave 3.0. Reward 4.0. Leadership
Development 2.0. It’s designed to represent
iterations and over time becomes a symbol for every
initiative being considered as an improvement area
in the months and years to come.
Self-Service FTW
There’s a small window in the early days of startups where you can get
away with highly unscalable solutions. In fact, there’s a lot to be said for
why you should embrace unscalable solutions for as long as possible
especially if there’s a highly personal and human component to it.
When you have 10 or 20 employees in your startup, you might not be
too concerned with managing leave in a spreadsheet, recruitment through
emails, and processing the odd expense claims when someone in the team
sends you a photo of their stand-up desk receipt. I’m not sure exactly where
the threshold is, but there’s a point in growing the team when the burden of
this administrative work becomes too much of a distraction on people in the
company who are likely managing people stuff in addition to their core roles.
The most common answer to this is “let’s hire someone to do the
work” which, despite the excitement that growing a team involves, is often
just managing a symptom of a growing team rather than the problem
8
itself. The question is not “who manages this work” or “how do we cope
with increased administrative work” but rather “how do we reduce the
administrative overhead our growing company is producing.” Hiring is
still a possible solution, but it’s the last possible solution as the goal is
ultimately to keep the smallest team for as long as possible.
For a lot of the administrative work a growing startup encounters –
expenses, leave, payroll, access to systems, etc. – I’ve found a lot of
success in using tools to drive self-service. Allowing team members to
manage their own administrative workload in a clear and accessible way,
supplemented with tools that automate as much of the process as possible.
There are cheap, even free, HR tools on the market to administer leave and
benefits including payroll inputs.
Similarly, automation workflows can help support onboarding and
offboarding procedures and distribute actions automatically across the
team after a trigger is passed. Central knowledge management tools
provide a single source of documentation and process so that the team
can self-serve the “know-how” of the company which saves a lot of back
and forth communication and even the need to run training sessions
sometimes too. The outputs of this work will still exist but only a fraction
of the work that originally existed, so this can either still sit as part of
someone’s role or can be outsourced to an accountancy, payroll, or virtual
assistance company for a few hours per week.
There will still come a time where the People, Finance, and Operations
areas will need dedicated in-house capability, or at least fractional where
more strategic work is needed, but putting in place efficient tooling that
automates administrative work and encourages self-service will delay that
need which is important. It will also mean that when the time comes to
hire into these teams, there is space for a more strategic hire that can focus
on the highest value initiatives to the success of the business rather than
just consolidating the administrative burden into them.
9
Decision by Committee Sucks

We had just concluded a recruitment process for a senior software
engineer. The process involved a number of team members who were
involved in the various assessment and interview stages. We came together
for a quick debrief after compiling our recommendations individually,
only to find a rough split across the team. Four people had suggested a
yes to hire, and two people had suggested no. We had two attempts at
this debrief to come to a decision with the manager clearly looking for a
group decision. In the end, the manager decided that as the group couldn’t
come to a single decision, that it was a “no” decision for that candidate.
This same process happened for a number of candidates. When the
recommendations were unanimous, we proceeded quickly. But when it
was not unanimous, we defaulted to no.
Now, there’s no saying whether each decision was right or wrong but
that’s not the point. The point is that a pattern existed of us delegating
decision-making authority to a large group of people and setting the
expectation for those people that they were operating as a committee.
It was probably more like a jury in practice, but let’s keep going with the
committee analogy.
That decision-making process within the committee was poorly
executed and the result was a slow and inefficient process and high risk of
a poor-quality decision too. There are several reasons for this:
• Recommendations were coming from people involved

throughout different stages of a recruitment process.
Those who were completing the technical assessment
were evaluating on a different set of criteria to those
completing the pair programming assessment, and
those doing the cultural interview. It meant the
recommendations were ultimately apples and oranges,
each grounded in different explicit and implicit criteria.
10
• We did not distinguish between feedback and

recommendations. We sought recommendations from
the team when what we actually needed was input to
the recommendation. This set poor expectations for
the team too, who initially responded positively to the
opportunity to play a bigger role in hiring efforts, as
they were often investing huge amounts of time into a
recruitment process and seeing very few people emerge
successful from it.
• We made a poor assumption that candidates needed

to tick every box. If a candidate performed really well
in all but one part of the recruitment process, the team
member who was in that one part of the process is only
looking through a very narrow window into how that
candidate may perform in the role.
• There was a bit too much desire to please and

agree from me, and likely the manager too, so if
the committee was split, we defaulted to the more
conservative option and encouraged the team that next
time would be different.
This example is rooted in a recruitment process, but very similar
behaviors happen throughout all sorts of team routines too. Picture the
leadership team who struggle to agree a way forward because some people
aren’t on board. We idealize consensus and agreement which doesn’t lead
to high-quality decisions. Or fast ones.
We made a lot of changes to our recruitment process to focus on
how we were making decisions. Most of these changes apply to broader
forums too:
11
• Clarity: Identify the decision-maker who is solely

responsible for making the call. They should be
the person who is accountable for the result of that
decision.
• Expectations: Set expectations with other team

members for what role they will play. In the
recruitment debriefs, we let team members know
the debrief will be to share their notes, observations,
examples, and any concerns relating to the part of the
process they were involved in.
• Partnership: Establish the People team as a partner to

that decision, helping the decision-maker consider the
feedback and input and prioritizing what is important.
• Get it done: Make the damn decision! As you will have

just read, done trumps perfect and all decisions carry
risk. So make yourself comfortable with that risk and
make a call. We won’t get them all correct, but it’s still
better than indecision.
• Communication: Communicate the why behind the

decision and genuinely recognize the input, whether it
supports the decision or not.
Beware the Magpies

If you’re unfamiliar with magpies, they are a beautiful black and white
bird with a reputation that precedes them. Magpies are known for their
attraction to shiny objects. Whether that’s actually true or not, and how
magpies actually perceive shiny objects, is beyond my knowledge. When
I was growing up in Australia, we would ride our bikes up and down
12
the street wearing brightly colored and sparkled helmets which would
encourage magpies to swoop and attack us. Seems pretty stupid in
hindsight.
Many years ago in the early days of my HR career I had a colleague
who described me as a magpie. I suspect it was meant as a subtle insult
but it’s something that has stuck with me for a while, both in terms of the
underlying message but also reflective of my behavior at the time. I was
an absolute sucker for opening up a magazine or LinkedIn, reading about
something I thought was really cool, and coming to work the next day
and wanting to implement it. A sales team with no commission structure?
LET’S DO IT! An entire company without reporting lines and job titles?
LOVE IT! An entire company where you get to set your manager’s, and the
CEO’s, pay? WHERE DO I SIGN UP?!
It might come as no surprise that once I joined my first startup, my
magpie personality started to reemerge. Faced with an environment that
was all about moving at pace, iterating, experimenting, and innovating, my
ears would prick up at any talk of the next revolutionary working practice
or something I heard at a conference or read online. This time around,
however, I was a bit more aware of what was happening and needed to find
a way to harness the magpie spirit without forgetting there’s a context and
thoughtfulness needed to make something work in that specific startup.
I started to build mental lists of what was happening within the
industry and the major shifts facing employers – from the rise of flat
operating structures to increased benefit flexibility, to really innovative
learning and performance solutions. I was consciously avoiding copying
and pasting the new, shiny ideas I was seeing elsewhere and starting to
think about what I could learn from those ideas and in what context there
would be value to rethinking our current approach.
I remember in the early days of a startup we were discussing learning
cultures and how to really ignite the curiosity and passion for learning
within the team. We had budgeted for training but the budget was rarely
13
used. There were also some conferences and workshops we paid for
but only for a very small number of the team who had put their hand up
and really pushed for it. This was also around the same time as we saw
the emergence of payments platforms that let you distribute budgets for
flexible benefits. Bingo! We put in place a learning budget that allowed
people to use virtual payment cards to self-service their own learning
resources. We removed the perceived barrier around needing to ask for
permission by removing all approvals and trusting that people will do the
right thing (98% of people did), and we integrated with a learning Slack
channel to automatically share what everybody was investing their budget
in. This was also a team accountability step – if you bought an iPhone with
your learning budget it would be posted on Slack for everyone to see.
What transpired after this was pretty special. People started making
recommendations to each other on useful learning resources. Small
teams started forming to participate in group workshops and conferences
together. We set up a company library of resources and playlists to help
folks interested in learning new skills. And it operated itself, with almost no
involvement from the People team.
Beware the magpies. There are a lot of us, and left unchecked, we are
directing energy into things that are not driving genuine value in a startup,
or any company for that matter. Help us build context for initiatives and
steer us back on course if the excitability is not grounded in what’s actually
important in the company.
our People Strategy Is Your

Y
Business Strategy
I once worked in a team where we presented the People strategy to the
company before the business plan was finalized. Which in hindsight feels
a bit odd. Where did the people strategy come from exactly? How did we
14
manage to identify where to focus our time, and communicate why that
was the case, when we didn’t yet have a broader business plan to guide the
direction of the company?
While it took a few detours through teams like that one, I’ve come to
learn that the people strategy is an enabler of the business strategy rather
than a stand-alone strategy itself. There isn’t a single pillar of a startup’s
strategy, or a single team within a startup, that doesn’t have a significant
component of their success directly related to people. Be it ramping up
customer success teams to deliver an exceptional, global experience for
customers. Or maturing a reward framework to drive a more predictable
cost curve. Or planning the growth forecast for investors to ensure there is
adequate, ramped sales capacity to deliver revenue goals.
I no longer invest huge portions of my time, even as a Chief People
Officer, designing a long-term people strategy. Instead, time is invested
in getting under the skin of all parts of the company, understanding
the challenges and performance drivers, and considering how people
solutions will drive the success in that area. And then we make it happen.
This reversal of approach does not dilute the people-first approach in
any sense, but rather offers significantly more buy-in around the work
that needs to happen when it directly impacts the performance of the
company.
Summary
• Ground your decision-making in data and make it
transparent. The goal is not to please people. Good
decisions sometimes piss people off.
• Avoid short-term temptations for bespoke employment

terms. You’ll build a people debt that comes back to
bite you in the ass once you grow.
15
• Perfect work rarely delivers materially more value than

good work in a startup, so get it done and trust your
ability to iterate it over time.
• Build automation and self-service into as many

administrative processes as possible to delay your need
to hire and reduce administrative burden.
• Be clear on how decisions are made and what inputs

are needed. Decision by committee is neither fast nor
does it result in a higher-quality decision.
• Every initiative you work on must be aligned to the

priorities of the company. Work your way inside out to
understand what people solutions will solve challenges
and enable success in each team. And beware magpies!
16
CHAPTER 2
Leadership
In the last chapter, we covered the myth that is the blank canvas we’re
building from and the paint that already exists on that canvas. Arguably the
biggest source of paint and the state of the business you’ve joined will be in
the leaders that are already in place. So in this chapter, I want to get under
the skin of startup leadership which, unsurprisingly, appears frequently in
my mental notes.
I have several shelves of leadership books in my home. Most of them
have imparted nuggets of wisdom or know-how into my brain, yet despite
having read so many leadership books, I still can’t say with any confidence
they actually prepared me at all for the realities of leadership positions.
The recognition that leadership is not a position is well understood, but for
the purpose of this chapter when I use the word leaders, I am referring to
those who are leading a team.
An investment in leadership is hard work, but well worth the return. It
might take a combination of developing existing leaders, promoting from
within and hiring externally. In many small companies, even before people
leaders are in place, they are seen as a hierarchy and structure, regardless
of the person and their style. Being clear on the “why” helps as does
casting a vision forward to how the company will grow over time. Most
importantly, it’s a recognition that leaders cast a shadow that runs deep
into a company, especially a startup, so it’s vital that shadow is having the
best possible impact on the team.

Chapter 2 Leadership
There are several parts to this chapter that cut across the People
remit. So for that reason, I’ve kept the focus on some of the key leadership
challenges that exist in a startup, kicking off with my three red flags. These
red flags are three things that are constantly sitting on my radar from the
moment I start with a company. When you get these right, the value is
immeasurable. When you screw it up, like I have a few times, the damage
takes a long time to recover from.
Red Flag 1: Lack of Leadership

Before you immediately think this is rubbish and startups do not
need more leaders, it’s certainly not lost on me that startups need a
disproportionate number of driven and capable individual contributors
compared to leaders. But let’s cast back to when a startup is 20 or so
people. In the initial, scrappy phases, the founder(s) were likely the
leader for everyone in the company. Even at 20 people it’s quite normal
for most people to be reporting to a founder, or at best there might have
been an early leadership hire into a sales, operations, or technical team.
As the team grows to 50 or enters the journey after Series A funding, the
roles and expectations of leaders fundamentally change. There is now a
need for leadership beyond the founder(s) who are also transitioning into
operational roles as C-level or senior team members.
During this phase, spans of control often balloon. It’s not uncommon
for one or many founders to have teams that are 10, 15, sometimes 20
people strong. Temporarily you can cope with a large span of control
before you usually see symptoms that it’s time to outgrow that founder-
central leadership structure. Your team will start to demand functional
expertise and mentorship. Founders will start to end up with remits that
are far too wide and result in ineffective leadership or burnout. Investors
will start to look for a transition away from founder-led success to
18
repeatable, consistent success. All of these symptoms point to the need to

make a deliberate and thoughtful investment in a leadership structure that
can scale the company through the next stage of growth.
There’s no exact playbook for this, but if you’re finding yourself in this
sort of environment, here are a few tips to start:
• Start at the top: Work with the founders and members

of the Board to build clarity on the substantive role
each founder will play. By substantive role, I mean the
one that’s not called founder. That is a large, heavy, and
very important hat to wear, but the founder will also
likely be the CEO, CRO, CTO, or some other role. That’s
the one I’m referring to. Their substantive role is vital
as the company moves from being founder-led to a
sustainable business engine.
• Accountability: Each role on the leadership team

should offer a single point of accountability for results
in their area. If you have a leadership team where
several members all own a revenue goal or the product
road map, you’re setting yourself up for conflict,
unnecessary meetings and bureaucracy, and a lot of
confusion within the team.
• Completeness: Collectively, the leadership team

should offer completeness. This isn’t to suggest you
need every functional leadership role immediately on
the leadership team, but rather if you consider your
challenges over the next 12 months, are there any
glaring holes? What areas of your performance and
strategy sit between teams or across teams? Is it clear
who on the leadership team will own these areas?
19
• Leveling: Be conscious of titling as the company grows.

If you’re 20 people with 8 customers, is the leadership
need you’re really describing that of a Chief Customer
Officer, or is the best skillset at the Head, Manager, or
Lead level. Unless you’re using titles to get you in the
room with prospects, strongly consider hiring at the
level that role needs in the short and medium term and
work hard to help that person grow into the next level
leader you might need down the road.
• Fractional leaders: Consider fractional executive

leadership if a full-time role is either out of the budget
or premature in terms of workload. A fractional exec,
particularly in key growth areas like Finance, GTM, and
People, offers a much more practical way to ensure
you’re focusing on the right things at the right time.
• Relevance to now: Consider the job description of every

leadership role in the context of taking you from point
A, where you currently are, to point B, where you want
to be in the next 12–18 months. Most leaders have a
sweet spot in a company’s growth journey so be very
mindful of hiring in leaders who are exceptional at
point D and point E when you’re nowhere near that yet.
You’re setting yourself up for difficult conversations
about 6–9 months into their tenure.
Make sure you have a passionate, committed, and capable people

leadership team before, and as you grow. It's rough ground without it.
20
Red Flag 2: The Wrong Leaders

It’s time to call a spade a spade. There are times throughout your growth
journey where you will have people in leadership roles who do not
embody the leadership behaviors, culture, and performance you’re trying
to achieve. You might be trying to strengthen accountability within your
team while your sales leader is overstating pipeline and close dates. Or
you’ve committed to becoming a more transparent company and your
operations leader is not communicating what they’re working on or
providing important data to others who rely on that to do their roles. Or
perhaps you’re taking on your team’s feedback in an engagement survey
around inclusion and having their voice heard and your product leader
continuously talks over others or shuts down any idea that isn’t their idea.
If you’re recognizing this sort of misalignment within your leadership
team, know that you’re not alone. It happens all the time. In most cases,
the reasoning behind the misalignment is quite innocent. Leaders have
built styles, preferences, and behaviors over their career and in some
environments they may be incredibly effective and in other environments
they can do a lot of damage. In a small number of instances, the reasoning
is less innocent and those leaders have more devious traits. Leaders cast a
wide and impactful shadow on those around them. Poor behaviors infect
teams and, if not managed, can influence the culture of those teams over
time which becomes more difficult to unwind.
Act early. Do not trust that the problem will fix itself. It won’t and great
talent are rightly impatient when it comes to whether they should stay or
go if they are experiencing the symptoms of a poor leader. Once a behavior
is called out, you owe it to the leader to help them change the behavior
swiftly and consistently. If they aren’t coachable or take the matter
seriously, they need to go. The damage a poor leader can do in a small
company is profound and it shouldn’t take great people leaving for it to be
dealt with.
21
Red Flag 3: Accidental Leaders

You’re a software engineer and an early employee at a startup. Initially,
your days are spent coding and building your product. The road map of
work, combined with greater support requirements and some projects
from customers, starts to outnumber you, so you hire someone into
your team. Then another person. And another. Then a few more. All of
a sudden, you’re now spending a disproportionate amount of your time
managing people and processes and not what you joined the startup to
do. You’re not complaining about it, but it’s not why you get out of bed
on a Monday morning and you might feel you owe it to the startup or the
founder to just keep going.
I call this accidental leadership. Through a long line of small changes at
a company, it’s where a talented individual contributor accidentally ends
up managing a team in order to keep up with the pace and delivery of work
at the startup. They become an accidental leader. Sometimes it happens in
months and sometimes in years, but to no fault of their own they’re now in
a leadership role by accident. It happens more often than we might think.
If a leader’s description of their perfect role at the company, and what
brings them energy and fulfillment, is not a people leadership position,
you need to act. I’m not suggesting you let them go but rather you need
to find a role that better aligns their strengths and interests with what you
need in your company, and appoint someone into the leadership position
who really wants to do that.
Accidental leaders can go unnoticed for years. It’s usually a
combination of factors that let it go unnoticed too. Fear of putting
their hand up and suggesting they’d rather be doing something else. A
belief that, over time, they’ll learn to enjoy their new role. Feelings of
commitment and loyalty to the founder or person who gave them the
opportunity. Or they’ve just been so in the weeds of the business that they
never really stopped being an individual contributor and they ignore or
avoid their role as a leader.
22
Accidental leaders can be inhibitors to growth, but seldom do they

carry the same risk or worry as a lack of leaders or the wrong leaders.
But they are a reality of a startup and it’s important to not let them go
unnoticed and ensure you’re having open and candid conversations with
them to create safety for the possibility that they might like to step out
of that role and do something else in the business. And that is the key
for accidental leaders. You don’t want to lose them and they likely don’t
want to leave, but you might need to reconsider the role that will let them
contribute their fullest and allow them to explore their passion again.
ot Everyone Wants to, or Should,

N
Be a Leader
We need to unlearn this idea that in order to develop your career, you
need to move into leadership. I cannot think of a more painstaking role
in a startup than leading a large team if your heart's not in it. One of my
personal lessons was assuming that leadership development was just for
leaders and future leaders, rather than it being about building the skills
and knowledge relating to leadership. I was reminded of this by a senior
individual contributor who had been in a leadership position before, hated
it, but was still passionate about building his skillset around leadership
knowing it was transferable into many parts of his role. It feels like a
rookie mistake from me in hindsight, but based on how many leadership
programs I still see that are only designed for those who lead teams, I
suspect it’s a pretty common rookie mistake.
There are two things I now try and make sure are crystal clear from a
leadership progression and development perspective:
1. Progression: Progression frameworks should have a

fork in them, where some people progress down the
path of leading teams and others progress through
23
more senior individual contributor roles helping to

shape strategy, make complex decisions, and take
on more senior responsibility. If your progression
framework is a single line, those in your team who
do not want to be a leader will hit a plateau and
likely look for that next experience outside of your
company.
2. Development: Leadership development should cater

for those in leadership positions and those who
are not. There is a safety you will inevitably try and
create for those in leadership positions to develop
their skills within an environment of peers, so some
delineation here is likely important. But those skills
you’re trying to develop around resilience, coaching,
motivation, feedback, communication, and change
are beneficial for lots of people to allow them to
progress and arm them to do their role to their
fullest potential.
The Psychological Safety of Leaders

Leading teams is hard.
Reading books (even this one), taking classes, listening to podcasts,
and going to conferences all tickle that curiosity and might give you a few
tips, but nothing actually prepares you for what it’s like. And once you do
experience the highs and lows that come with leadership positions, it can
often feel like a lonely place. If you’re reading this right now and feeling
like a bit of an imposter, or that you’re not cut out for leadership, or you’re
looking around and seeing others who are seemingly more confident and
comfortable in their leadership roles, know that you’re not alone. I see you.
24
I’ve been working with, or part of, leadership teams for the last decade.
I’ve worked alongside leaders who have had moments where they feel they
have conquered a mountain, and moments where they feel completely
inadequate. I, too, have felt that way. What is missing from the leadership
rhetoric, particularly in growing startups, is the expectation placed upon
us to be and act a certain way. To have time for everybody but still have
time for ourselves. To be thinking strategically and making long-term
decisions, but still be close to the day-to-day work. To be poised, calm, and
positive in the face of adversity, but not so much as to be inauthentic. To
express vulnerability, but not so much to be seen as weak or incapable.
The weight of this expectation can be crippling and I’m convinced that
if more people knew how it actually felt being in a leadership position, it
might not appear so regularly in career development discussions. This
might sound pessimistic, but the rose-tinted facade placed over moving
into leadership positions and how great it is to make decisions and earn
more money results in nothing more than a leadership honeymoon before
the reality of expectation sets in. Some leaders in startups navigate this
really well and find balance between the expectation and fulfillment. Other
leaders do not, and end up feeling pretty miserable or in some cases doing
a lot of damage to the startup cultures they’re operating in.
It took me a few years to really feel comfortable, or at least less
uncomfortable, in leadership positions. I had to navigate feelings of
inadequacy and also show resilience for when things went wrong, which
was often. What helped me was deeper than just a great manager and a
network of people in similar roles. I leaned heavily, and still do, on a small
and trusted set of people who I feel 100% comfortable being myself and
having a no-bullshit conversation around what was happening.
For you, it might be a mentor, therapist, former colleague, or significant
other. I found the safety and candor that existed in these relationships
allowed me to understand more about the gap between the leader I was
(and am) and the leader I want to be. It’s also helped me realize that I like
25
balance in the role between operational building and leading teams which is
why I try and make sure I’m the first People boots on the ground in a startup
where I find that balance over the next few years of growth is spot on.
If Difficult Conversations Don’t Affect You,

You Shouldn’t Be Having Them
Earlier in my career, I found myself a regular member of project teams who
were put together to enact restructures and reduction in force. There were
always a very small number of people satisfied by the prospect of receiving
a severance package as they neared retirement or were considering work
elsewhere anyway. For the most part, though, the people on the other side
of a conversation with me and their manager were neither expecting it, nor
did they want to hear the news. Randy, who had a stay-at-home wife and
small child and was now wondering how to make ends meet. Alison, who
relocated internationally for the role and would no longer have a working
visa to remain in the country. Ashley, who recently took out a mortgage
and now faces severe financial pressures. Each of these folks had their lives
uprooted because of things well outside of their control and by people
who, at best, could only empathize with how that felt rather than actually
understand it.
During one particular restructure, I was sitting in a meeting room
with our project lead. We were discussing some of the conversations that
needed to happen and my emotions started bubbling to a point where I
couldn’t suppress them. I was feeling a lot of things but one in particular
I remember vividly and, even to this day, the feeling hasn’t completely
subsided. I felt guilty. That it was my fault that so many of my colleagues
were now out of work. That the pain they experienced hearing that their
role was going to be removed from the company, and the aftermath of this,
was my wrongdoing.
26
It was the first time in my career I’d become quite emotional and, for
me at the time, it was a signal that I was no longer the right person for this
sort of work. I wasn’t resigning, but I wanted out of the restructuring and
all of the difficult conversations that came with that. I was a blubbering
mess in a meeting room with the project lead, making my case for why
they needed someone more experienced and more resilient than me to
take over. I was clearly not fit for the job.
“If you want out, I’ll make it happen. But your empathy is a
strength, not a weakness. If difficult conversations don’t affect
you, you shouldn’t be having them.”
I don’t think they intended those words to have such a profound effect
on me. It’s been years since that conversation, but it’s something that I find
myself reflecting on and revisiting often, especially in startups where the
environment is more volatile and difficult conversations more prevalent.
We’re now accustomed in startups to hearing stories of being laid off
by a group video call, an email to a personal account, or even when an
access card doesn’t work at an office. Behind the scenes, the argument
leaders will be making is the need to execute these changes with pace
and efficiency. To make the decision, move onward and keep building
toward the startup vision. Here’s the thing. Outside of a small group of
stakeholders, this replacing of difficult conversations with impersonal
behaviors is not seen as efficiency, but rather cowardice. We have to
unlearn that it’s acceptable to avoid difficult conversations and remove
humanity from difficult decisions.
We owe it to our team and those around us to experience those difficult
conversations fully. If they make you feel like crap, good. That’s what it
means to be human and make difficult decisions relating to people. If
you’ve just let someone go or given some really tough feedback, you’re
likely only feeling a fraction of the difficult emotions that the other person
is feeling. And if you don’t feel anything when making those decisions,
maybe you’re not the right person to be making them after all.
27
ometimes to Show You Care, You Need

S
to Show Your Teeth
I wrote these words down within minutes of a leader saying them. We were
working together to deal with a fascinating challenge around performance
and attitude. A member of the team found fault in everyone else’s work
except their own. They gave feedback to others freely and without second
thought and regardless of the impact it had, but when faced with feedback
they closed up, externalized, and disagreed. When assigned work or a
project, it was met with support if it involved doing things they enjoyed
doing, and was met with avoidance or pushback when it didn’t.
The reason this was fascinating was because of the polarity of
responses. Their work was not of poor quality. Quite the opposite in fact.
But the impact they were having on the team environment was terrible,
and they had quickly built a reputation both within their team and across
teams as being a bit of a brilliant jerk. Other members of the team didn’t
want to talk to them, let alone work with them. And so the manager
decided to have a conversation with them and provide them some
feedback about the impact of their behaviors and to discuss some ways
they could start to work on that together.
Shortly after, the team member pulled me aside with quite a dramatic
monologue about the inappropriateness of their manager, that they
wanted the manager to face disciplinary action, and that they wanted to be
moved into another team. There were also some pretty wild accusations
and assumptions about the manager’s background and their abilities. The
manager never knew the details of what the team member shared with me,
but they were aware that they were “reporting this to the People team.”
In the days ahead, I learned of another conversation the manager
had with the team member. This time, they took a different approach.
The manager shared clear examples of what was happening, made it
crystal clear to the team member what was expected of them, expressed
28
disappointment in how things had progressed, and then laid down

clear consequences for their employment if immediate change didn’t
happen. The team member was asked to take the rest of the day off to
reflect on the conversation, and they could either return the next day
committed to working in a new way or they could consider this a formal
employment matter.
In my chat with the manager, they said it was an overdue conversation
that they wished they had done earlier but didn’t want it to be perceived as
not believing the team member could get to where they needed to be. But
to show you care, sometimes you need to show your teeth.
This was not a case of rain one day and sunshine the next. There were
challenging moments for months, but the signs of improvement were there
and slowly the team member started to get out of their own way and realize
the impact they could have with a more constructive way of working. And
it made me appreciate the link from the manager between having a truly
candid and open conversation with a deep care for getting the most out of
a team member.
By definition, leadership cuts across all areas of the people and culture
remit so this chapter touches on several of the different milestones and
stages of the people experience. In the next chapter, we’ll take a more
detailed step into Culture, which in the startup space is about as fluid as
it gets.
Summary
• Identify areas of the company where there is a lack
of leadership capability and accountability, where
the wrong leadership behaviors are playing out, or
where accidental leaders need safety to move out of
their roles.
29
• Leadership is hard and not for everyone. Embed

into progression and development programs the
option to pursue people and non-people leadership
roles. If you are in a people leadership role, find that
psychologically safe space to share your highs and lows.
• We can’t, and shouldn’t, avoid difficult conversations.

It’s human for us to be affected by them and that is not
a weakness. Sometimes those difficult conversations
require us to change tune and show our teeth to get the
best outcome for someone.
30
CHAPTER 3
Culture
The link between leadership and culture is undeniable, so it is only
logical that after exploring leadership red flags, safety, and capability in
the previous chapter, this next chapter will explore the flow-on effects to
the shadow that leaders cast. This chapter is all about culture and, as you
will see by the first lesson, it starts with having a shared understanding of
what that means. Once we have that, I’ll share with you some of my most
impactful mental notes from startups around autonomy, process, values,
layoffs, and of course, the great culture fit vs. culture contribution debate.
ulture Is Not Free Beer, Fruit, and a

C
PlayStation
If you’ve ever visited a career page for a startup and been hit with images of
people drinking, sitting on bean bags, and playing table tennis, you’re not
alone. After all, what better way to highlight how fun a work environment
is than to promote images of people doing anything other than work.
Combine this with things like free beer and PlayStation as benefits in the
job description, and who wouldn’t want to join, right?
There is nothing wrong with this stuff because some people enjoy it.
But it’s not your culture. In the world of startups, there’s a history of relying
on beer and table tennis as symbols of coolness, culture, and “how we put
people first!.” And it worked for a while. But most people have clued on to the
vanity and are demanding a lot more transparency around actual culture.

Chapter 3 Culture
Culture is deep and it pays to get under the skin of a company and really
understand how it works. At its simplest level, culture is just a way to describe
how stuff happens at a company. How do people communicate? How are
decisions made? What happens when shit hits the fan? Does everyone rally
together or do people start pointing fingers or working in silos?
It may be very possible that several cultures exist within your company.
It might be driven by teams. Or the location of your people. Or even the
tenure of your people (think “old guard”). Culture is inherently fluid
both in how people can influence it and how people perceive it. A small
company with little to no hierarchy and decentralized decision-making
may be described as being both fast-paced and autonomous by one
person and chaotic and stressful by another. Both are valid perceptions of
culture that we need to own and work on rather than wasting time trying to
convince anyone that table tennis is culture.
Culture matters to people. It’s why many join a company, and it’s
usually what drives people away. So much so that many job candidates are
also suspicious if things seem too good to be true. Because they probably
are. If people don’t feel empowered by leaders, have tension and barriers
between teams, and don’t feel a sense of accomplishment in their work,
the free beer and fruit basket isn’t going to keep them around very long.
The best thing we can do is be authentic and transparent around the
actual culture of our companies. Highlight the great stuff that our people
tell us is meaningful. And then highlight the culture challenges and how
we’re approaching them. No workplace is perfect and, in my experience,
people value honesty, transparency, and commitment over vain attempts
to define culture by what’s in the fridge.
Culture Contribution or Culture Fit

When you’re small enough to count everyone on your fingers, your culture
is likely more fluid than you think. Sure, you might have extremely strong
traits and behaviors from existing team members that anchor the culture.
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Chapter 3 Culture
But if you’re planning to double or triple in size, your culture is going to

change. The question is not whether you can stop the change, but rather
whether you’re up for defining and managing that change purposefully
and in a way that allows your business to keep both the special sauce that
makes you “you,” and evolve in a thoughtful and deliberate way.
We’ve been throwing around the term “culture fit” for decades.
Sometimes it’s for exactly what I’ve described earlier around evolving a
deliberate culture without losing its special sauce. Sometimes it’s for a very
different purpose that allows bias to play out freely and, as a result and
perhaps unfairly, it’s increasingly seen as something we should be wary of.
You’ve probably seen the rhetoric in more recent times around culture add
and culture contribution rather than culture fit.
Culture fit never stopped being relevant. It was just bastardized over
time as a poor excuse for letting our similarity biases play out and hiring in
the shadows of existing team members. It’s the equivalent of me building
a business, hiring a bunch of folks who look like me, talk like me, think
like me, and act like me, and then calling it culture fit. We also see it rear
its head throughout recruitment processes as the catch-all reason why
someone doesn’t get a job. Candidates spending three, four, or five hours
in interviews and being told they aren’t progressing with no more detailed
feedback from a hiring manager than not being a culture fit.
It’s no wonder that it’s become tarnished. But those examples are simply
bad leadership behaviors playing out, not an invalidation of the concept
of culture fit. I remain a huge advocate of what culture fit can and should
be. Checking the alignment of values and traits of new team members to
the company. Ensuring that someone joining or even moving to a new
role internally is set up for success and can thrive within that operating
environment. If you’re hiring into a 50-person startup to establish the first
customer success function, you’ll likely be looking for someone who gets their
kicks from creating and building order within unstructured and ambiguous
environments. Someone who is comfortable building processes and new ways
of working where they likely don’t exist before. That’s a form of culture fit.
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Similarly, if that startup values transparency and there are rituals

around transparent learnings, results, successes, and failures, you should
be looking for a strong culture fit within interviews around how they have
or would demonstrate transparency within their role. Without that culture
fit, you’re likely putting someone in a very confronting situation once they
start if they aren’t already aligned with your values.
Let’s talk about culture add. The rebirth of culture fit to reflect that the
last thing we want to be doing is hiring a bunch of mini-me team members.
Unsurprisingly, I’m a huge advocate of this too and I don’t believe it’s
mutually exclusive with culture fit. Keeping with the customer success
example, I remember hiring for a startup’s first customer success leader.
The startup already had some bits and pieces in place, but following some
team changes and a record-breaking year of new customers, we were
in need of a CS leader to wrap their arms around the entire remit and
build out an effective and scalable function. The leader we hired was a
resounding “yes” at every stage of the recruitment process, and if we were
explicitly scoring on culture fit and culture add as part of it, they would
have scored highly on both. They demonstrated a strong alignment with
our company values and no shortage of examples from their experience
to back this up. They also shared, in detail, the specific challenges and
solutions they’d faced coming into startups at a similar stage where there
was very little in place other than high expectations and demands. We
were confident in their ability to excel within our culture and how we
operated as a startup. Culture fit.
What made us excited though wasn’t this alignment and fit with the
startup. It was what they would contribute to our ways of working, values,
culture, team, and growth that didn’t already exist within the team.
Experience and perspective from incredibly diverse industries. Countless
examples of innovative thinking and breaking traditional rules (some we
believed in too) to get impressive results. At each interview stage, we left
feeling like our thinking and perspective had been stretched. If we hired
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Chapter 3 Culture
this CS leader, we’d be pushed in an uncomfortable but necessary way

in order to build a customer experience that was both incredible and
scalable. Culture add.
There should never have been a debate around whether culture fit or
culture add was the goal, because it’s not an “either or” scenario. When
you’re building your team and iterating your culture in a deliberate way,
you’re looking for both. A fit within your values, norms, and the stuff
that makes you special to make sure someone can be successful in that
environment. And an addition and contribution to your culture that brings
breadth to your perspective and, hopefully, even makes you feel a wee bit
uncomfortable.
What Does Autonomy Look Like for You?

“Why do you want to join our business?”
“I really want to work for a startup.”
“Why’s that?”
“I’m looking for more autonomy in my role.”
“What does autonomy look like for you?”
It’s a common conversation that most startup recruiters will relate to.
The candidate who comes out of a large, corporate organization and wants
to experience the roller coaster that is a startup environment. During the
recruitment process, there’s a word that always pricks my ears up and
something that has become synonymous with startups. Autonomy.
Autonomy in the workplace has fascinated me for years. We read books
about why it’s a must-have in order to achieve engagement from your
team. And it’s something that so many people seemingly are striving for in
the workplace too. But something has always made me feel a tad uneasy
about autonomy, which is that for each person what autonomy means
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Chapter 3 Culture
can vary quite significantly, and that it’s not automatic that people thrive
with autonomy. So I’m always curious when a candidate in a recruitment
process talks about autonomy, what do they actually mean. What does
autonomy look like for you?
“I want to make decisions.”

“I want to have my voice heard and a say in how things
are done.”
“My manager is a micromanager and I don’t like that.”
“I want more flexibility in how and when I do my work.”
“Things feel so bureaucratic here and I just want to GSD.”
Every one of these among dozens of different responses to what

autonomy looks like for candidates, ranging from leadership roles,
developers, salespeople, graduates, and even the People team. And every
one of these touches on interesting facets of culture and how people
perceive autonomy. Autonomy in a startup is a unique thing. The level of
responsibility and proactiveness needed can thrill some people, and shock
others. Clarity is not a given, nor is direction sometimes, so autonomy
can be as extreme as complete self-ownership and governing of our roles
and their outputs especially in the early days. In terms of finding culture
fit and alignment between how someone best contributes and the culture
of the company, I can think of very few more important things to discuss
candidly and transparently than that of autonomy.
They want to make decisions? What sort of decisions? Can they share
more about a time when they wanted to make a decision but couldn’t,
and what happened? Are there situations where someone else making a
decision would be received poorly by them? What’s their thinking process
behind important decisions – do they consult, engage, and inform?
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Chapter 3 Culture
Your manager is a micromanager? What support and behaviors do

you look for from a manager in order to do your best work? What level of
autonomy feels right for you in this sort of role? What behaviors does your
manager display that make you feel micromanaged? I’ll almost always
ask that last question when micromanagement is raised as you might be
surprised how often the simple action of being assigned a project or asked
for a one-off status update is seen as micromanagement.
While the general feeling of having more control and ownership of
what you’re doing fits firmly within autonomy, it’s such a critical part of
culture fit that it’s worth investing a bit of extra time to discuss and make
sure you’re aligned. Otherwise, if they’re looking for a highly autonomous
role where they decide what they work on and when, and that’s not the
level of autonomy you have within your company, you’re setting them up
to walk through a revolving door.
Process: The Enemy or the Hero?

I LOVE a good process. The simple art of determining the effective steps in
order for something to be completed consistently, repeatedly, at pace, and
helping everyone else has clarity at the same time. Right? Right?! At least it
should be.
If you’ve ever joined a large company, you’ll be met with established,
documented processes before you even start on your first day.
Preboarding, onboarding, compliance training, policy documents,
checklists, and that’s before you’ve even started doing any work. And
once your feet are under the table, you’ll have operating processes,
SLAs, workflow maps, RACI frameworks, and all of the other process joys
designed to achieve what we described earlier.
If you’re joining a startup or very small company on the other hand,
you’re going to be met with very little process and structure. They’ll likely
have some compliance steps along the way but otherwise they’re doing
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Chapter 3 Culture
well if they have any sort of onboarding or operational processes if they’re

still in a scrappy phase. Process, implemented at the right point in time
and with the right conditions, can be hugely effective in helping a startup
mature how they operate from scrappiness to repeatable and consistent
success. We see it in sales teams when playbooks, methodologies, and
territories all start to emerge. We see it in product teams when road maps
are formed, sprint cycles are put in place, and quality assurance are
embedded into how the team operates. And we see it in People teams
when hiring and onboarding become a priority, if performance and reward
need linking and even for simple things like leave and payroll.
There is, unfortunately, a dark side to process. When we prematurely
introduce it, or we implement a process that is not reflective of where the
company is at in their journey. It’s well intended but dangerous overkill
and runs a real risk of both hampering pace and progress and disengaging
early-stage employees who thrive in the scrappy and unstructured
environment. There is always a time and place for it, and we need to make
sure we don’t make process the enemy to our progress.
One of the most common process pitfalls happens around approvals.
As the company grows, there comes a need for more mature governance
practices. Typically, you want approvals to sit at the lowest possible
levels in order to keep processes effective but also demonstrate enough
governance to avoid risk. Take something like new vendors, something
which all startups will eventually have a process in place and something
that touches a lot of different teams. Now picture a 100-person startup with
this uncomfortably common process.
An engineer is working on implementing a new alerting technology
and has identified a vendor to deliver this. The engineer needs to submit
a proposal to their manager, then to their two-up manager, and then
to the Finance team. The Finance team then seeks endorsement from
the founder who still wants to be across all new spend decisions. Once
the spend is approved, the engineer needs to get IT to approve the
implementation, Legal to approve the contract terms, Finance to again
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Chapter 3 Culture
approve payment terms. And if this process happens for every new
vendor, on spend over a low threshold, and with a bunch of internal
documents and procedures to match over email, you’re requiring your
engineer to spend days of time preparing and trying to get everyone to
approve it before they’ve even started implementing a new alert system.
If that engineer has been around the company for a little while too, they’ll
remember vividly how easy it used to be, “in the good old days” when they
and their manager could pump out all of that work for a $5k contract in an
hour or two and make it live by end of the week.
While process is important at times, overusing it in growth-
stage companies starts to chip away at the pace and agility that likely
differentiate you from bigger players in the market. Things will slow
down and become more structured at some point, so best not to force it
prematurely.
ut Only When Is Absolutely

C
Necessary to Survive
I used to be part of a business where restructuring happened so often to
cut costs that the HR team started to be viewed as redundancy squads. It’s
really hard to achieve anything meaningful in your people strategy when
there’s an underlying sense of “Am I next?,” as even once a restructure was
complete those who remained remain unsettled without the friends and
colleagues that were once part of their team, and wondering not if another
restructure will happen, but when.
In startups, we face a similar cycle sometimes when a company’s
revenue doesn’t keep up with its spend, or when there’s pressure from
stakeholders to reduce the burn rate if the startup isn’t profitable yet. It
pains me to hear of stories where teams are ripped up while executive
bonuses are still paid, folks are still traveling business class to conferences,
consultants and vendors are being paid tens of thousands of dollars, and
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Chapter 3 Culture
no one is really sure what value comes from it, and yet in order to “position
the business toward sustainable growth,” there needs to be a reduction
in workforce – which, while we’re taking aim at this, disproportionately
affects people and talent, marketing, operations, and customer success
teams where apparently they are only valued when growing. OK, that felt
good to get off my chest!
There are times when reducing the size of the team is absolutely
necessary, and I get that. But it should never be the first lever you pull. The
cultural damage it causes along with the slow rebuilding needed if things
pick up are both huge deterrents to leaders and People teams. It should be
the last lever you pull, and done in a way that preserves the values of the
company and nurtures both those who are leaving and those who remain.
Reducing the size of the team is an expensive exercise, both in terms of the
financial cost to do it properly and the emotional and well-being cost that
will drag for months or years after it happens.
If you’re faced with a challenging commercial environment and under
pressure to reduce costs, here are a few things I’ve learned from having
been through this far too many times.
E xhaust Every Other Option First to Bring

Spend Down
I cannot restate this enough. Go line by line through where you’re
spending money in the last six months and challenge everything. While
some of these numbers won’t look big, if the spend is not critical to what
you need to do in the next 12 months, set it aside to review options to
reduce or remove the spend. Things like travel, entertainment, software,
consultancy, facilities, and services are all great places to start and you
only need a handful of cost-saving opportunities in these areas to be
equivalent to headcount costs. Some benefits can even be reviewed, but
be cautious about touching anything relating to people’s sense of security
such as health insurance, life insurance, retirement accounts, etc.
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Chapter 3 Culture
E xplore Staff Cost Reductions That Don’t

Eliminate Jobs
Cost reduction and elimination are two different things, but when we’re
sitting in a room trying to find ways to reduce staff costs, we default to
eliminating jobs and going through redundancies. In one startup I’ve
been part of, the CEO initiated a series of staff cost reductions that made a
significant impact on the burn rate and didn’t require anyone to lose their
job. Here’s what they did:
• All members of the leadership team took a pay

decrease.
• No bonuses were paid or budgeted for.
• All pay increases that year were frozen, except for those
below an income threshold.
• Employees were offered the chance to go part-time

temporarily. Some took that option.
• Some employees were offered to transition and be

trained up in new roles when their team workload
reduced. All of them took up that offer.
Do It Right and Look After Your People

If every other option has been exhausted and the business must reduce
the size of the team, I urge you… do it right. Your business is worth nothing
without your people, so look after them. There could be an entire chapter
on this so I’ll summarize the most pertinent points.
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Chapter 3 Culture
Communication
Your communication plan should be thoughtful, comprehensive, and
sensitive. This means, at a minimum, that every single person in your
company or the affected teams have several touchpoints of communication,
both verbally and in writing. This should include a one-to-one conversation
for both those whose roles are impacted and those who will remain. If you
do not have the expertise in house to do this, go and get it. Please, do not
attempt a workforce reduction if you’re never done it before. I’m all for
learning on the job, but in this case, learn from someone who has done it
before and done it well. If you have investors, reach out to them first as they’ll
likely have connections and can refer you to someone who can help.
Severance
Never forget that the people who are impacted by this decision are
exactly that. People. Who might have kids, a mortgage, travel plans,
caring responsibilities, health concerns, and all sorts of other things.
The statutory redundancy payment in most countries is the minimum
payable, not what you should be aiming for unless a meaningful severance
is going to compound the financial problems. This may sound a bit
counterintuitive, but if you’re laying off 10% of your workforce, you can
definitely afford meaningful severance payments.
Benefits
In a similar vein to severance, the benefits offering and continuation of
these is a must-have. This is not the time to strip away employment from
your people, and then leave them high and dry without many benefits and
coverage that can be tricky to replace while looking for their next gig. Make
sure healthcare coverage is continued as much as you’re able to in their
country of employment. Ensure outplacement and mental health support
is on hand for at least three months after someone leaves. And if you offer
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Chapter 3 Culture
equity, don’t put your people in a position where they have to fork out
huge amounts of money to exercise their options in a company they’re no
longer part of.
Diversity
A forgotten step most of the time. We’ve already discussed bias and how
it can impact recruitment decisions. The same thing applies here and the
same level of calibration is required. Be mindful of your legal obligations
too in this space, especially around those on extended leave or who have a
protected characteristic.
Redeployment
If you’re trying to reduce the team size in one area of the business and
continue to grow in another, redeployment needs to be front of mind.
While you may feel some or many skills are missing from those who are
impacted in one part of the business, don’t forget the knowledge and skills
that they do have. The inside know-how, relationships, understanding
of your customers and product, and the fact they are already in your
business. The cost of training and redeploying will almost always far
outweigh the cost of hiring externally.
Find a Common Language

When you double (or more) in size, communication becomes just that little
bit harder. It takes a bit longer for messages to sink in. It might take several
attempts to communicate. You might have to adjust mediums or invest
in new mediums to find ways to best connect with a growing team. That’s
where a common language is helpful to bridge communication gaps and the
conflict that naturally emerges. I’ve found three forms of common language
help to add some glue to the culture and support growth of the team.
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Chapter 3 Culture
Values
I’ll come on to values more deeply in the next lesson. Once they’re
documented, build them into recruitment steps and performance
feedback processes. Talk about them regularly. Recognize others for how
they live and role model the values. Deal directly with behaviors that aren’t
aligned to the values. They are the strongest glue that exists in a culture
and have the power to drive common behaviors across teams and ensure
you attract people who are going to excel in your company.
Ambitions and Goals

I have a bit of a checkered background with Objectives and Key Results
(OKRs) as a company-wide goal methodology. One day I’ll nail it, but
having been underwhelmed with how I delivered these in the past, it’s
taught me something even more important. The value and importance in
every single team member knowing exactly what the company is trying
to achieve. This shared understanding helps to keep people pointed in
the same direction and fosters good conversation around how we invest
our time and resources. Without transparency and symmetry in this
information, you create forks in the work people do and end up needing
to spend time realigning on priorities. If you’re a CEO reading this, the
test for goals in your company, regardless of how you choose to structure
these, is that every quarter you should ask a random handful of people
across teams and levels to articulate the goals back to you. Make sure they
don’t think it’s a test and they know you want to check how well they’re
communicated. The aim is that every single person you ask can describe
them, whether they’re your VP Sales or a Graduate Software Developer,
and understand why they are important.
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Chapter 3 Culture
Work Styles
As teams inevitably grow, tension and conflict becomes normal. It’s
nothing to be afraid of. Great teams have conflict and work through it
constructively. But one of the most difficult things when conflict exists is
being able to understand where other people are coming from and being
able to safely describe what is taking place. Typically, we apply judgment
language to what we observe. Tim is not being direct, he’s being rude. Alice
is not being thoughtful and considered, she’s being slow. Ryan is not being
sociable and energetic, he’s annoying me because he doesn’t shut up and
let me speak.
I’m a big fan of the Insights Discovery tool and framework to help build
a common language around what we observe in others and ourselves in
the workplace. How we communicate, behave, manage, make decisions,
and perceive things. All difficult to describe because we struggle to know
what words to use. Instead of being frustrated that someone wasn’t on
board for a project we were experimenting with, we could instead become
curious as to whether they had a need for more concrete details and data
behind the decision, and start a conversation around that. There are lots
of tools out there that might help with this, but for me I keep coming back
to the simplicity of Insights to help navigate the complexity of human
behavior.
Getting Past the Values Fluff

You walk into an office to interview for a new job. You’ve spoken to a
recruiter and things sound good so far, but you’re still working out if this
is the right company and role for you. Culture is important and you’re
wanting to look under the hood and check that this is what you’re looking
for in your next gig. You approach reception to let them know you arrived.
Plastered behind the receptionist you get a glimpse of the company
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Chapter 3 Culture
values and hope that they give you a bit of insight into the culture: respect,
integrity, and professionalism. How helpful.
At this point in my career, I have pretty polarizing views of company
values. I have seen just how powerful they can be when they articulate
specific, unique, and embedded parts of a company culture and just how
sticky they can be for teams to encourage mindsets and behaviors. But too
often I’m left reading the company values on a website and not knowing
much about the company at all afterward. Take something like integrity.
Integrity is a minimum requirement and expectation for running a
company. While I’m sure some folks adopt practices that lack integrity, it’s
a license-to-operate trait of your company, not a value.
Great company values help define who you are as a company and what
makes you “you”. Every company should have integrity. And respect. And
professionalism. So what do you have as part of your culture that makes
you “you”?
The best way a company value has ever been described to me is
through the lens of a trade-off. The trade-offs you make highlight the
values you have. You might value transparency, but are you willing to be
transparent even when things are uncomfortable, or if the message is a
bad one? That’s the trade-off you make when you value transparency.
It’s not required of you, but you’ve chosen to behave in a certain way that
indicates what you value. I’ve also found questions like “what does a high
performer look like here?” and “how do we make decisions?” to be helpful
questions to help elicit insights on the values of a startup.
Once values are identified, the trade-offs for each will help to inform
the next level of detail which is to articulate the specific behaviors that
demonstrate that value. This is hugely important as how one person views
transparency will differ to the next. The trade-offs help everyone in the
company understand how to apply that value to how things get done in the
business. This is also the level of detail that will help inform how you hire,
manage performance, and recognize people.
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Chapter 3 Culture
This chapter has covered a handful of traits and implications of the

work we do around culture, but you may have noticed it was absent from
a lot of what we’re learning about how the work we’re doing to build
diversity, equity, inclusion, and belonging can impact on the culture and
experience of our people. The next chapter is called Inclusion, a chapter
close to my heart and critical to how we build startups.
Summary
–– Culture is a fluid fabric of systems and behaviors. It’s
how stuff happens, not what’s in the fridge.
–– Culture fit and culture contribution are currently

fighting for attention, but it’s never been an either/or
battle. When you’re building your team in a startup,
you need to be looking for both.
–– Put a common language around the business and

culture as you grow. It helps you work through conflict,
focus on culture fit and contribution, and build align-
ment to goals.
–– You can’t be values-led without a significant trade-off
to demonstrate it. Narrow in on the trade-offs you make
that demonstrate what your values might be.
–– While process is important at times, overusing it in

growth-stage companies starts to chip away at the pace
and agility that likely differentiate you from bigger
players in the market. Things will slow down and
become more structured at some point, so best not to
force it prematurely.
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Chapter 3 Culture
–– Reducing the size of your team is a last resort, not a first

one. Exhaust every other option first to reduce spend,
look for ways to reduce staff costs without losing jobs,
and if you need to make that difficult decision to let
people go, your people deserve for it to be done sensi-
tively and generously.
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CHAPTER 4
Inclusion
Inclusion hits home for me, so it only felt appropriate to have a chapter
dedicated to it and some of the lessons I’ve learned both within and
outside of startups. With this chapter, we’ll have covered the impact,
shaping, and shared understanding of leadership, culture, and inclusion,
before we then tackle some of the specific areas in the People lifecycle that
influence the experience we’re crafting.
I covered my sexuality for years before I felt safe enough to share
that part of my identity with those around me. That’s not just a work
story. I covered it from everyone, a common experience for the LGBTQ+
community. But I saw the work side of it too. The unease I felt when a
supervisor was scared that a gay man would hit on other men in his team
or the guilt I felt lying to my teammates when they would ask if I had a
woman in my life yet. This has nothing to do with my managers either. I
couldn’t have asked for better managers throughout most of my career. I’ve
been very fortunate on that front. This relates to embedded, cultural norms
for what was accepted, believed, and tolerated in a number of businesses I
was part of.
There was no way this book would ever be finished without dedicating
a chapter to inclusion, and there are a few reasons for that. The first
reason is my own experience. This book started as a journal of things I
was learning and things I didn’t want to forget, and my own experience
and perspective on inclusion features frequently. Another reason is
the constant reminder of just how far we have to go before every single
workplace is somewhere people feel belonging, safety, and acceptance.

Chapter 4 Inclusion
And the last reason is how integral the work we do in this space is to
every other part of people and culture in a business. You can’t convince
me you’re serious about culture and leadership which we just covered in
the last two chapters, or performance and reward which we’ll cover later,
without showing me first how serious you are about inclusion.
As a small disclaimer, I’ve called this chapter inclusion and I use that
word quite frequently throughout. It’s how I’ve come to understand parts
of my own experience. I know the work we’re doing is much broader than
that, and captures accessibility, belonging, diversity, equity, and justice.
For consistency, I’ll use the acronym DEIB for diversity, equity, inclusion,
and belonging as that most accurately describes the experiences and
perspectives I share in this chapter.
Inclusion > Diversity

Earlier in my career I was given some “advice” by a colleague that I should
be mindful of my body language, otherwise people would think I bat for
the other team. And one of the first times I told someone in that workplace
that I was gay, the response was asking me whether I wanted to be on the
company’s LGBTQ+ parade float that year. Not bad for a company who
touted their LGBTQ+ awards and credentials.
I don’t know about you, but there are very few things I find more
misguided than reading a company’s DEIB plan and not seeing anything
more substantial than representation targets and broadly stated intentions
around equity, inclusion, and belonging. One of my favorites is just
how many companies of all sizes believe that by sprinkling some visible
diversity into its senior ranks that they’ve solved the rest of the acronym
too. A HR leader even tried to convince me that more women on teams
would lead to greater inclusion across the company, so the focus needed
to be on “only hiring women.” I have no doubt some good intentions
are buried in there somewhere, but unfortunately we’ve hit rock bottom
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Chapter 4 Inclusion
where the average company has stripped back DEIB to nothing more
than making sure there is some visible demographic diversity and a few
rainbows and cupcakes throughout the year.
The obsession with showing people something visible, and perhaps
the fear of being seen as not doing anything visible, should never
have replaced the need to actually do the work to become a company
where everyone, in whatever way you choose to define diversity, can be
successful and contribute to the company’s success. A team representing
20 different demographics can be full of conflict, disharmony, and
exclusionary behaviors. Similarly, a completely homogeneous team across
the same demographics can demonstrate a high level of inclusion and
belonging.
Let’s apply this to a small and fast-growing company. The value of
diversity comes from diversity of thought. It’s critical to a small company
looking to innovate or disrupt a market. In my experience, what we call
diversity now in terms of demographic diversity is simply a proxy for
embedding more diversity of thought and reducing the inequities that have
prevented this from being accessible in the past. But aiming for diversity
without inclusion, equity, and belonging is just setting the company up for
great talent to leave.
Each time I’ve come into a startup, I’ve learned to start with inclusion.
And there are two pockets in startups that are full of actionable insight and
opportunities to build inclusion.
Leadership
Calling out behaviors and actions that don’t promote inclusion. Observe
team meetings, communication, how decisions are made, and who is
involved. There’s no sugarcoating this and I’m starting with it for good
reason. It’s hard work and all sorts of uncomfortable, but if you’re a senior
people leader or, better yet, a founder, you’re in the best seat to do this. I’ve
found a happy ground somewhere between “not trying to make friends”
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Chapter 4 Inclusion
and “not approaching things with a stick,” which is to use observation

feedback models to identify specific behaviors that don’t drive inclusion
and suggest an alternative way for a better result. Most people are willing
to do this, even if it takes a few goes (yes, change can take some time). If
they aren’t willing to try, they shouldn’t be part of your company.
Backyard
This is a catch-all for the people systems, policies, and processes which
are part of how your company runs. It’s how promotion decisions are
made, how recruitment takes place, career development opportunities,
pay gaps, and benefits. All of these areas are carriers for exclusion and
reinforcing stereotypes which makes a great stomping ground to make
genuine impact.
Take something like parental leave where, in most countries, it’s
designed to support the notion of a childbearing woman taking an
extended period of leave to care for a child while a man takes a long
weekend and returns to work. Now consider how your parental leave
applies to different circumstances and family structures. Adoption.
Surrogacy. Same-sex couples. Single parents. Stillborn and miscarriages.
Heck, even dads in the stereotype above who were prevented from more
time with their new bundle of joy. When you consider the breadth of
circumstances relating to parents, most company (and statutory) parental
leave structures are highly exclusionary and reinforcing of stereotypes.
Not convinced? Reach out to a half dozen parents in your network
who don’t fit the stereotype described earlier and ask them to share their
experience of parenthood and parental leave. That was how I came to the
realization that I needed to rethink everything about parental leave in the
companies I work in.
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Chapter 4 Inclusion
Pitch at 80%
This isn’t exclusively for this chapter and it builds upon the “Done >
Perfect” learning in Chapter 1, but it originated in my work in this space
and I’ve come to accept it as a personal principle in pretty much every part
of my work. In fact, it even applies to the publishing proposal my publisher
received for this book and, thankfully, that seemed to go OK!
While my career in more recent years has been in the startup scene,
I used to work in a really large company and corporate environment.
Between the number of stakeholders needed to get something over the
line and the number of people impacted by the decisions, I found myself
making sure something was as perfect as I could make it before I brought
anyone into the fold. This isn’t bad behavior, just symptomatic of how I
was operating at the time and the environment I was in.
On advice of a mentor, I started to push myself to share ideas and push
for changes when they were roughly 80% done, either in terms of planning
for projects or even 80% baked in my mind for sharing my thinking. The
thinking here was twofold: nothing is perfect anyway, so pace of delivery
and having impact sooner rather than later outweigh the other 20% of
perfecting; and it was important for me to get used to the fact that things
fail often in startups and that’s OK, so assuming what I’m proposing is
reversible if things don’t work out, I should accept the higher risk of failure
and get comfortable with that.
Pitch at 80% is the result of this and something that feels more
comfortable now than what it used to. When a thought is 80% baked, I’ll
share it for others to provide their perspective on. It ensures I never get so
hell-bent on having the right solution that I’m not open to others’ ideas
and feedback. And when my work is 80% complete and the remaining 20%
is just perfecting it, I’ll get it out into the open or, better yet, make it live
and trust iteration to fix the rest.
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Chapter 4 Inclusion
e Judged by Your Actions, Not

B
Your Intentions
I presented this learning and now principle on a video call with 30 or 40
team members of a company as part of a DEIB presentation. I was asked to
speak and share the initiatives and progress we’d made in the startup I was
part of. I can’t remember the exact phrasing of how I introduced this, but it
was along the lines of “don’t believe anything until it happens.” I probably
looked like a bit of a pessimist but I’m not sure that’s ever a bad thing in
the DEIB space these days. Optimistic with a healthy dose of caution and
skepticism might be a better way to put it.
The DEIB space is flooded with good intentions. The company
sprawled over social media for injustice telling everyone how much they
care about the feedback and experience of employees and how committed
they are to change. The company with a 20% gender pay gap reflecting
on International Women’s Day about the incredible women who have
been integral to their success. And let’s not forget the company pocketing
profit after adding a rainbow to their product range for Pride. These are all
actions from companies we’ve sadly become accustomed to.
In one of the first startups I worked in, we made a deliberate choice
to reframe our communication in the DEIB space to being about what
we had done, not what we were planning to do. While we knew the areas
that required change, the act of sharing plans can sometimes trap us into
thinking the work has been done. And when we’re called out on that,
we repeat the vicious cycle of making clear our intentions and plans.
Intentions are cheap. For progress to be real and impactful, we needed to
be accountable for our actions and the results of our actions, not for what
we were planning to do. And so that is what we told our people. Judge us
by our actions, not by our intentions.
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Chapter 4 Inclusion
In the years ahead, DEIB in this startup felt different to any other
company I’ve been part of. We used data to inform our progress and areas
that still needed work. The gender pay gap reduced from some absurd
number to near 0%. Policies and people processes were continuously
iterated and then tested for feedback in terms of the impact they had.
Churn did not disproportionately impact some communities over others.
Neither did engagement scores. When we were asked to share our DEIB
Strategy or Policy as part of an RFP process or through due diligence, we
took pride in saying “We don’t have one, but here’s the impact we’ve had.”
And if you needed any more convincing about why Inclusion > Diversity
from the start of this chapter, the diversity of our team started to increase
on a whole host of different demographics. Not because we set targets and
had DEIB plans in place, but because what we had achieved and built was
now resonating with a much larger population.
Get Under the Skin of Your Gender Pay Gap

It’s hard for this to not be the next logical learning given the focus so far
on inclusion and accountability. Time and time again, I find the gender
pay gap to be as divisive as it is telling about where a company is at in
their DEIB journey. And regardless of the arguments for why and how the
gender pay gap emerges in a company, doing nothing or even settling for
incremental progress can’t be the solution.
“It tells me if I’m valued and how much I can earn here.” These words
from a woman I worked with sum up everything that People teams,
leaders, and founders need to know about the gender pay gap. It’s also just
as relevant to any pay gaps that exist across other demographics and can
highlight where inequities exist through other decision-making or people
processes which need some love, such as recruitment and promotions.
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Chapter 4 Inclusion
For the purpose of this mental note though, I’m going to refer only to the
gender pay gap with what I’ve learned in startups being applicable almost
identically across other demographics too.
One of the biggest misconceptions around the gender pay gap is that
you fix it by paying the lower-paid gender more. Sure, you could grab some
duct tape and make it look better, but this ignores the actual problem.
Work in this space needs to look not only at what has happened historically
and what the data says, but also what caused it to exist that way in the first
place and what changes to company processes can prevent inequity from
creating the same problem in the future. There is nothing about the gender
pay gap that is accidental. We created it.
Depending on where a startup is incorporated and operating
will depend on when legislation makes reporting on gender pay gaps
mandatory. But the best time to start, whatever stage you’re at, is right now
with the data you have available. In a nutshell, there are two types of pay
gaps and both are important to analyze as they’ll tell you different things:
equal pay gap and gender pay gap.
The equal pay gap, in its simplest form, means the same pay for the
same work. There are valid reasons why pay might differ within roles such
as through a performance process, but the heart of equal pay is really
testing the structural and systemic issues that result in a gender pay gap.
In many countries, where there are no valid reasons why pay differs, it is
considered a breach of law.
The gender pay gap is the more nuanced of the two. Compare the
average hourly earnings of men to the average hourly earnings of women.
The percentage difference between the two is your gender pay gap. Let’s
say you have a gender pay gap of 10%, meaning that the average hourly
earnings of women are 10% less than that of men. There are lots of reasons
this might be the case, but regardless of the reasons, the gender pay gap
still exists. The average woman, regardless of role, tenure, and seniority,
can expect to earn 10% less than men in your company.
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Chapter 4 Inclusion
If you have a big enough data set, you can cut this across roles, tenure,
and seniority to see if you can pinpoint some insight around what might
be causing this. In startups I’ve been part of, we’ve identified a bunch of
reasons why a gender pay gap exists:
• A leadership team made up of mostly men
• A higher proportion of women in part-time roles which

had lower average hourly pay than full-time roles (lots
to unpack in that one, but more common than we
might hope!)
• Technical teams made up of mostly men where salaries

were higher than nontechnical teams
• A higher proportion of women in entry-level or junior

roles, often as a result of trying to increase gender
representation and immediately going to the graduate
and entry-level roles where recruitment pipelines are
more balanced
Each one of these tells a story of something that is relevant to the

outcome. They may not be directly related to pay, but they influence the
outcome. And back to the misconception around paying the lower-paid
gender more, we could indeed do that, but none of the preceding examples
are actually changed by that. We’re just re-creating the problem to exist
again but with a different baseline.
In the previous learning around actions and intentions, I mentioned a
startup where we brought the gender pay gap down to almost zero. There
were three areas we focused on which over a three-year period demonstrated
year-on-year reduction to zero. And just in case you were thinking this, no, it
didn’t then create a gender pay gap the other way. It stayed within a couple
of percent either way of zero consistently after that. These changes were not
designed to increase one gender’s pay, but rather to remove the reasons why
one gender’s pay was increasing disproportionately to the other.
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Chapter 4 Inclusion
Area 1: Recruitment
Recruitment is a deep pit of behaviors, systems, and processes that
contribute to pay gaps. We started first with reviewing all of our language
and job requirements to broaden the pool of candidates who would
read our post and be excited by what they could contribute. Narrow
salary ranges were added to all advertisements to remove asymmetry of
information. We then built a standardized approach to hiring stages and
calibration of decisions to avoid any unwanted effects of bias. I’ll come
back to this in the next lesson. Our final piece in recruitment was the
“best offer first” principle which leveled the negotiation playing field that,
historically, disproportionately benefits men.
Area 2: Progression
Up until 50-ish people in a startup, progression isn’t much of a thing
especially if you’ve grown quickly to get there. The early dozen or two
team members don’t usually have progression as one of their top draw
cards and, frankly, organizational structures that early are fluid and messy.
That’s not an excuse to not care about it. It’s just something that tends to
be down the priority list when you’re desperately trying to build and ship a
product. Plus, it’s not normally something that will break the organization
immediately if you don’t have much in place. Key word there is definitely
immediately.
In my experience, during periods of intense growth in the early stages,
progression decisions are typically made on the trust of the founder(s)
or CEO. Add that to unclear leveling and role scopes, lack of internal
recruitment processes, and a healthy dose of urgency culture, and it’s
not hard to see how progression decisions can perpetuate imbalances
in both representation and compensation. We focused on leveling and
role definition (i.e., levels of authority, responsibility, influence, and
contribution), and paired that with a formal internal recruitment processes
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Chapter 4 Inclusion
with diverse panels and calibration of decisions. In under two years, the
percentage of women promoted increased from roughly 25% to just under
50%, and the percentage of other underrepresented populations also
increased but to a lesser extent. We focused on the process that caused the
imbalance and allowed it time to demonstrate impact.
Area 3: Compensation Framework

OK, I’ll admit that frameworks around compensation can be a bit divisive.
I’ve dedicated an entire chapter to it, but in practice, there have been
enough lessons throughout my career on compensation to fill a separate
book. But for the purpose of this lesson, I want to target one specific
element of a compensation framework which is the benchmarking and
structure of compensation ranges and levels which form the spine of any
good framework. This was single-handedly the most impactful initiative
we did to reduce the equal pay gap. We defined and leveled every single
role in the organization, sourced multiple, reputable data benchmarking
sources, and built a philosophy behind how we set salaries using ranges
that were informed by that data.
The reason why this is so impactful is twofold. Firstly, it takes most of
the guesswork out of it. Sure, you’re not going to impress everyone with
this (remember “Ground Your Decision-Making”), but adding a dose of
data corrects the imperfections of how humans approach compensation.
And the ultimate test should always be if you can easily justify your
decisions to an open room of everyone impacted by it. The second reason
this creates impact is because it allows a swift rectification of errors and
the history of imperfections that have been built up. The first time I built a
compensation framework and applied the principles, it reduced the equal
pay gap to 0% and the gender pay gap significantly too (not to zero though
as that didn’t happen for a couple of years). Fixing the structure meant we
could focus on other barriers without the anchor that would be a systemic
issue like the compensation framework.
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Chapter 4 Inclusion
The Myth of Removing Bias

I am biased. You are as well. But there’s no need for either of us to be
defensive about it as, unlike we are led to believe, bias is unavoidable. As
humans we are a collection of experiences, perspectives, norms, beliefs,
and products of our environment. These shape everything we do and how
we see things. So it should be no surprise that bias comes up so frequently
in DEIB conversations.
Yet for the last ten years the majority of training sessions and
presentations I’ve attended around bias have focused primarily on how
you can root out bias and stop it. You can’t. With some deep introspection
and a lot of self-awareness, you can be hyperaware of your bias. And over
time it’s likely possible that bias can change, as does the lens through
which we view the world. But you can’t stop it completely.
I remember the first time I did one of those implicit association tests as
part of a training session. It showed that I displayed a handful of positive
and negative biases toward a whole bunch of different demographics.
No doubt incredibly useful to reflect on and I think about it often. But
in this training session, we weren’t reflecting on bias or what to do with
that information. We were holding up results arguing who was better.
Celebrating results that were less strongly weighted than others. And
treating bias like something we should be ashamed of and hide from.
It was a friend’s perspective during a rant we were having about bias
which felt so perfectly articulated and captured the frustration in my mind.
It immediately featured in my mental notes. “Don’t be scared of bias. Be
scared of letting bias play out in your company”.
The fact I have biases built up over my lifetime and influenced by the
experiences I’ve had is not something to be ashamed of. It is something to
identify. To understand. And to make sure that those biases don’t influence
the decisions and choices I make. And as a People Ops leader, it’s my job
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Chapter 4 Inclusion
to have processes and systems in place that can do this at scale across how
the company operates. To calibrate decisions and broaden the input. To
enrich conversations with different perspectives. To call out behaviors or
gut feelings that people don’t want to elaborate on. And to help others
become curious about their own biases and build the awareness to identify
how they might play out.
This chapter felt personal to write and share, because it is. It’s personal
to everyone regardless of their background and something we simply
can’t afford to not get right if we’re serious about what we’re building. In
the next chapter, we start our exploration of specific parts of the People
lifecycle and experience, kicking off with Recruitment.
Summary
1. Representation matters, but it can’t be the sole
aim of your DEIB work. Start with inclusion and
focus on the pockets of the business at high risk
for non-inclusive outcomes (e.g., leadership
behaviors, communication and meetings, policies,
and processes that impact people directly, such as
recruitment, leave, and promotions). Getting this
right adds credibility to the other work you will
need to do.
2. When something is 80% formed in your mind, start

sharing it with others for input and feedback. The
remaining 20% will allow for buy-in and prevent
perfectionist behaviors from delaying something
that can deliver value.
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Chapter 4 Inclusion
3. The DEIB space is flooded with good intentions,

but our actions and results leave a lot to be desired.
Intentions are worth nothing. We are accountable
for what we deliver and the impact it has, which
is the standard we should apply to any DEIB work
that we see.
4. The gender pay gap has become a divisive topic but

is ultimately a test of so much more in the people
space than just compensation. Getting under the
skin of what drives it, where inequities exist, and
how to right these allows us to tackle the problem at
the core, not just try and manage the symptoms.
5. Bias is a normal, unavoidable, and human

experience. We shouldn’t be scared of it or try to
deny its existence. We should be scared of letting it
play out unchecked.
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CHAPTER 5
Recruitment
Now that we’ve looked under the hood at leadership, culture, and
inclusion that sit throughout every part of the People space, it’s time we
tackle the very start of how our people experience startups: recruitment.
This chapter is bittersweet. The state of recruitment has a long way to
come, but hopefully after this chapter, you’ll be excited as I am by what is
possible if we reframe recruitment in a more people-centric way.
In 2022, I decided to run a bit of an experiment and set up an Ask-
HR-Anything thread on a careers forum. The forum is anonymous so I
wondered if it might prompt some radically transparent perspectives on
HR. Plus, if it meant I could help a few people out who might be in pickles,
then it was probably worth it.
About 50,000 views and almost 2,000 responses later, there was enough
insight and material to write an entirely separate book. Once I got through
the deeply offensive and abusive comments that the keyboard warriors
posted, the single most concerning area was hearing about the state of
recruitment. From people who were laid off, had applied for hundreds of
jobs, and rarely ever heard back. To those who went through ten stages of
interviews only to be ghosted and not receive any feedback. To hard-core
task rounds where candidates would work for days on end, basically as
free labor, to produce presentations and initiatives that would help that
company and then be told the role was on hold. There was even someone
who traveled hours by car to get into a city, bought new clothes for an
interview, turned up at the office, and was told the interviewer was not in
today and they needed to reschedule.

Chapter 5 Recruitment
I’m not blind to how much repair work there is to do in HR and how
mixed the experience is. But this thread was so hard to read. It doesn’t
matter the industry, country, or profession, candidates everywhere
are being treated like shit in our hiring processes, and it’s become so
consistent that we’ve learned to accept it as normal. One day I might
dedicate an entire book to this topic, but for now, here are some of my
learnings and musings on recruitment from scaling startups.
espond to Every Single Job Applicant

R
As Though Your Brand Depends on It
You're scrolling through LinkedIn seeing if your next opportunity might be
out there.
You stumble across a really interesting role.
The company looks great.
You meet the requirements they've listed and you start to get excited.
You open up your CV and start to mold it for this role, calling out things
in your background that are most relevant.
You put together a cover letter making it crystal clear why you're
excited by the role and what you can bring to the company.
You attach the documents to the application, answer some questions
about yourself, and click send.
Done!
And now the waiting game starts. You check your emails in the days
afterward hoping for a quick and positive response.
Then a few weeks later you still haven't heard back and you start to
lose hope.
You never hear back.
I once shared this scenario at a conference talk in front of a room of
recruiters and asked everyone to put their hands up if they've experienced
a company never getting back to them after applying for a job. Almost the
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entire room put their hand up. I then asked those people who respond to
every single job application they receive to put their hand down. A small
handful put their hands down. Around three quarters of the room kept it up.
The job application process is broken. We've created a norm in
companies where candidates are inferior. We then prove it to candidates
with disclaimers on the bottom of job advertisements like:
Due to the high volume of applications we receive, we are

unable to respond to every application and will only be in
touch with those who will progress to the next stage of the
recruitment process.
As a candidate, this is read as:
Despite me investing 30 minutes of my time putting together a

thoughtful application, you can't find 30 seconds of your time
sending me an email to say I've been unsuccessful.
The irony of this scenario lies in the fact that those companies who
receive such a high volume of applications will almost always have an
applicant tracking system (ATS) in place that allows for bulk rejection
emails, and those who don't have one in place are unlikely to be receiving
a high enough volume of applications to justify why they can't respond
with a friendly “no” to provide the applicant some certainty. In both cases
the reasoning usually lies somewhere between laziness and disrespect
for the job application process. As a job candidate the only thing worse
than a rejection email is hearing nothing back at all. It's both the sense of
rejection and hope combined.
As a People profession, we have to change this norm. Instead of telling
applicants on the advertisement that they may not receive a response, tell
them how long they can expect to wait before receiving a response. And
hold your teams and hiring managers accountable for ensuring every
single applicant receives a response if they were successful or not.
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Start with Your Best Offer and Don’t Budge

If it wasn’t bad enough for candidates to navigate a broken job application
process, unfortunately the offer and negotiation process isn’t much better.
Companies are generally focused on keeping the offer within budget
which unfortunately is interpreted by HR and hiring managers as keeping
the offer as low as possible. Candidates are, rightly so, focused on getting
the best offer they can. And neither side to this equation is particularly
motivated to speak transparently first about their expectations.
Job searching and recruitment processes are really unforgiving. At
the point you’re speaking to a candidate, it’s likely they’ve faced delays,
radio silence, and rejection. It also represents something far greater to the
candidate than it does the company. For that reason, I’m always of the
belief the responsibility to mend this should start with the company and
it’s the reason I now, almost religiously, use a set of principles to guide the
offer experience:
• Transparent salaries: Share the salary range on the job

post. There are some roles, despite opinion, where this
is actually really tricky in a startup. These are usually
roles that carry significant equity or variable packages
where the makeup of the package is flexible in order
to land the right hire. But for the other 98% of roles,
there is zero downside to posting the range on the
role in order to manage expectations from the start.
If you’re worried about what existing team members
will think when they see a salary range that might be
higher than what they are on, you need to fix your own
backyard first.
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• Screening: In the initial screening conversation, discuss

the salary range again and aim to understand the
expectations of the candidate. If you’re up front about
the salary range on offer, most candidates will share
their expectations with you. Two things to be mindful
of here:
1. If you share a range with a candidate, it is

human nature for the candidate to share their
expectation at the top of that range. Don’t be
annoyed, you would do the same in their shoes.
I find it’s helpful to also articulate how the salary
will be set within that range in order to ensure
parity with existing team members and reflect
how their capability and skills are assessed in
the recruitment process.
2. Some candidates will tell you their expectation

is above the range with the hope the range is
flexible. Again, don’t be annoyed. There are a
lot of reasons why a mismatch of expectations
exists. When this happens, I’ll usually reconfirm
the range with the candidate and what the
upper limit actually is, and ask them, “if you
were successful in this process and we offered
you [insert upper limit salary], would it be a
dealbreaker for you?.” If the answer is no, you’ve
set a reasonable expectation for the candidate
as to what is coming to avoid surprises. If the
answer is yes, you’ve saved time for both you
and the candidate for a role that is just not a fit.
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• Best offer first: At the offer stage, I use a “best offer first”
principle and I’m explicit about this with candidates.
This isn’t some fluffy way of polishing a low ball. If
you’re going to use this, it must be genuine; otherwise,
there’s zero value in it. Best offer first refers to discussing
internally at what point someone could keep negotiating
before we eventually say no. Let’s say you’ve set a range
of 60–70k. You offer 64k. If they really pushed for more,
you realize you would be open to 66k, but any higher
would sacrifice parity within the team. You should just
offer 66k and don’t negotiate. There are a few things I’ve
come to observe and realize from using this approach:
1. You must be explicit about what you’re doing.

Share the principle with the candidate. Tell them
how you arrived at that number and that it’s the
best offer first with no room to negotiate up. And
remind them the criteria in your decision is based
on where you’ve positioned them within the
range and why, and the high-level summary of
how that compares with existing team members.
If you are not explicit about what you’re doing,
they are at risk of just assuming they are being
lowballed. Because let’s be honest, this is exactly
what happens in most offer situations.
2. I’ve used this principle in three different startups

now. In every startup, the offer acceptance
rate increases and the time to respond at the
offer stage decreases. If you’re genuinely doing
good by candidates, they’ll recognize it. And
the company benefits from higher and faster
conversion rates.
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3. Be mindful of cultural differences. I first

introduced this in a European setting and the
results were immediate. When I introduced
it into a US setting, it was more problematic.
Candidates would come back a few days later
trying to negotiate it up, often above what was
shared as the salary range. We discussed this
within our US team and one of our sales team
members reminded me how ingrained it is for
her to never accept the first offer regardless of
how good you might think it is, and if you don’t
ask you don’t get. I respect that. It just makes
the best offer first principle a bit slower. In
the US setting the time to respond decreased
but immaterially. The offer acceptance rate
still increased in line with other regions, but
we’d often find ourselves in a negotiation
conversation simply saying no and reminding
candidates of the best offer first principle.
our Candidate Experience Is As Important

Y
As Your Customer Experience
If you’re in a company where your candidate is also likely to be a customer,
this learning will probably resonate more clearly. After all, you don’t want
to piss off a candidate who might already be or is considering becoming a
customer of yours. In a “to-business” setting, this link can be easy to forget
but I’d argue it’s still just as important.
In startups, we think about the customer experience often. Daily. But
rarely do we hear conversation of the candidate experience unless you have
a well-developed talent acquisition team. In the same way we map out
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the customer experience, it can be helpful to do that for the recruitment

process too. Identify the purpose and aim for each step of the recruitment
process, starting with how a candidate will initially discover the company
and experience a showcase of culture in an authentic way. Then, speak
to all new hires in the last six months to understand their experience of
the recruitment process, in particular what they found was helpful and
valuable and where things weren’t as sharp as they could be. Be mindful
that your new hires were successful in your recruitment process so they
likely only represent a very small percentage of the candidate experience.
Consider building feedback mechanisms into various stages of the
recruitment process. If you’re setting up templates in your ATS to progress
someone from screening stage to interview stage, you can build in pulse
check scoring and a focus question to get some real-time input. A focus
question like “What is one thing we could have done to make your first
stage interview even better?.”
Another key part to candidate experience is speed. Gone are the days
where it is acceptable for someone to receive an invitation to a screening
stage six weeks after they applied. Similarly, waiting weeks after an interview
is a surefire way for the candidate to lose excitement in the role. I use three
targets and metrics in the recruitment process to provide insight into speed:
1. Time to respond to an application: two weeks
2. Time to hear back after a main stage interview:

three days
3. Time to hear back after a final stage

interview: one day
There are, of course, instances where other interviews need to be

conducted before arriving at a decision. When this occurs, we use the same
targets but from the end of the last interview. If you don’t have an automated
way to collect this data yet, you can still embed a positive candidate experience
around speed into your process. At the end of each stage of a recruitment
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process, let the candidate know when they’ll hear back from you. It creates
some accountability between you and the candidate, and it helps manage
expectations so the candidate knows when it’s the right time to follow up.
Turn the Tables

To make the best use of this time, I’d like to spend the first half
of this interview with us getting to know more about you and
what you can bring to this company. Following this, we’ll turn
the tables so you can interview us and make sure you have
enough information to know if this opportunity is right for
you. And for the final few minutes, I’ll cover the next steps in
the recruitment process and when you can expect to hear back.
It’s easy to forget that a recruitment process is a two-way assessment.

Companies are trying to work out if someone is the right hire for the role,
and candidates are trying to work out if you are the right company for
them. It begs the question as to why so much of the recruitment process is
a one-way assessment.
In the past when I’ve been hiring into my team, I’ve often used the turn
the tables approach as part of a main stage interview to provide space for
candidates to get under the skin of the company and understand if it’s the
right fit for them. The more a candidate can learn about the role, team,
company, challenges, culture, and manager, the more armed they are to
self-select in or out of the recruitment process. Both self-selections are
valuable outcomes to a recruitment process.
Don’t Join This Company If…

One of the questions I was asked by a candidate during a turn the tables
interview has stuck with me for years. Amusingly, it’s also a question I
make sure to ask any company I am speaking to about a potential role also.
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Who shouldn’t join this company?
I like this question for a number of reasons. Firstly, you’re reframing a

question in a much more pointed way that allows you to get under the skin
of the culture of the company. Secondly, it’s really obvious to the candidate
when someone is full of it when they answer. You can’t waffle your way
through it. You’re forced to think about the circumstances in which
someone might not be the right fit at the company. And that’s a really
helpful thing to know up front, for both the candidate and the company.
As a candidate, I find the answers I’ve received from companies have
carried more emotion and authenticity in the response. I’ve learned about
previous people who they’d parted ways with. I’ve learned about cultural
challenges they have and are working through. I’ve discovered fears and
concerns of the hiring manager and also what is going to be important
for them.
It’s also become a go-to question when briefing new roles with hiring
managers. It helps understand specific behaviors or mindsets that can
be tested early in the hiring process, and in a similar way to interview
situations, it’s often an unexpected question that forces an authentic and
emotional response.
T he Candidate Was Great! I’d Like to Meet

a Few More Though
A pet hate of every talent acquisition professional. You’ve expedited an
incredibly talented candidate to an interview with the manager. They
might have come through an application process or someone you’ve been
proactively nurturing until an opportunity arises. The manager interviews
the candidate and it goes really well. And then the dreaded comment… “I’d
like to meet a few more candidates in order to compare.” Face palm.
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There’s a reframing in hiring that is really helpful to consider this

frustration. It’s describing the importance of hiring a great person for the
role, rather than hiring the best of the people we meet in the recruitment
process. This works in both directions. When an amazing candidate
comes along, you have to jump on them and back yourself. And if you’re
interviewing lots of candidates and none of them are at the level you need,
it’s far better to hire no one rather than the best of the bunch.
The comparison effect in hiring also rears its head when there isn’t
enough clarity on what makes a great candidate for this role. There are a
couple of ways to counter the need from a hiring manager to meet other
candidates following an exceptional interview:
1. Current team: If the role is not a new role, and there

are already existing team members doing the same
or similar roles, ask the hiring manager to compare
the candidate against their high performers. If they
can see the candidate on par with someone in the
team who is excelling, they are more likely to want
to avoid any risk the candidate drops out due to
delays. Similarly, you can ask them if they’ve hired
this sort of role in other companies in the past which
can be helpful if it wasn’t too long ago.
2. Grouped interviews: If the role is a new role for the

team or company, it’s helpful to group the first
couple of interviews together to counter this exact
risk. This requires some planning at the shortlisting
stage, but it reduces the likelihood you end up with
an outlier candidate who is at an opposite end of the
process to all other candidates.
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3. Role description: If you’re finding yourself in the

situation where it isn’t possible to group them
together and the interview has happened, it’s worth
going back to any notes from the briefing or role
description to where the hiring manager described
the candidate profile they’re looking for. In this case,
you can use these conversations as a quasi-
comparison of the candidate to the success profile.
4. Keep the ball rolling: If all of the preceding ways fail,

tactically, it’s best to keep that candidate moving
through the recruitment process rather than delay
until other interviews are held. In this case, it’s worth
checking with the candidate where they’re at in
other processes, and aim to book the next stage a
few days or a week out to allow a bit more time for
other candidates to reach the interview stage. This
doesn’t solve the comparison needed from the hiring
manager, but it does help play the cards you’re dealt.
In the next chapter, we’re going to tackle a topic that is never short
of strong opinions, varied practices, and a whole lot of complexity. So
it should come as no surprise that the mental notes I have taken, and
continue to take, on this topic are full of mistakes, lessons learned, and a
few pointed observations. Let’s talk Reward.
Summary
• So many parts of the hiring process are broken. We
have an opportunity to do good by people and offer up
a candidate experience with care, speed, and respect at
its core.
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• Best offer first principles can drive tangible results and

reduce asymmetric information in the offer process.
• Reframe hiring to be about hiring someone who is a

great fit for the role, not hiring the best person from the
candidates you’re interviewing.
• Demonstrate two-way interviews by turning the tables.
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CHAPTER 6
Reward
In this chapter I’m grouping together all things compensation, equity, and
benefits into the catch-all that is reward. And, if we’re joining a startup, our
first interaction with reward would have happened right at the start of the
last chapter on recruitment (hopefully because of pay transparency!).
I spend a lot of time thinking about reward, and in companies of all
sizes too, not just startups. It’s an area I’ve made a lot of mistakes and felt
like I’ve been continuously iterating, and as I alluded to earlier, even after
over a decade of working in and around the reward space in companies, I
definitely do not feel like an expert.
For this chapter, I’ve selected some of the most powerful lessons
I’ve had to learn along the way in a startup environment. It’s a topic that
is deeply strategic given its financial impact, very difficult to reverse
decisions, and is heavily linked to our psychology, emotions, and
wellbeing. There is no other part of the People space, or any chapter in this
book, that has a greater span of outcomes on the business than reward.
When we get it right, it’s a game-changer. When we get it wrong, it’s
destructive.
Design for the 99%

The saying “don’t design policies for the 1% of people who abuse them”
or words to that effect has been floating around People circles for years
now. It’s a fundamental mindset shift to what the previous decades of HR

Chapter 6 Reward
practice have taught us. Protect the business. Manage risk. Mitigate edge
case scenarios. And we’ve ended up with policies, contracts, benefits,
and programs that have so many restrictions and clauses that the average
employee feels like a child.
In the benefits space specifically, having too many restrictions in place
just in case the odd employee tries to abuse it very quickly discourages
others from using the benefits in the way that they could. It’s a careful
balancing act as, on one hand, there will always be someone who will be
devious and push their luck and you can’t ignore that, but on the other
hand, the more trust and freedom you give your people, the more they will
value and utilize the offerings in front of them.
Here are a couple of ways to build for the 99% and rethink benefits in
the workplace.
Learning Budgets
We’re making a needed transition from company-provided training to
the concept of each person having a learning budget to invest in their
development. Learning budgets help us to think more broadly around our
development and have flexibility with the type of development too. Not
everyone learns by going to a conference. Having implemented learning
budgets now a few times, there are a couple of watch-its that can enable or
hinder success:
• Put the learning budget in the hands of the learner: If

the learning budget is a line item on a spreadsheet and
I need to submit an expense claim or request for an
activity to be paid, I’m putting barriers up for people
to use it. Expenses assume I have the funds to pay for
something and wait days or sometimes weeks to be
reimbursed, which is not the case for a lot of people.
Similarly, if I have to request for an item to be paid for
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by the company, I’m less likely to suggest something

that might not fit the expectation for my role (e.g., a
customer success representative wanting to complete
a coding course). There are dozens of solutions on the
market to allocate budgets and payment methods to
employees that bypass both of these challenges.
• Use guidelines to help people understand what

professional development is: I made the mistake of
assuming everyone knew what the learning budget was
for. And then I started receiving questions like “can I
buy this book on product management even though
I’m in sales” and “is it acceptable to use the budget on
professional memberships.” So we built guidelines that
everyone could see that helped people answer those
questions and also think creatively around learning.
We included some examples of impactful learning
initiatives others had invested in, but also addressed
things we wouldn’t accept so people didn’t have to ask
what they thought might be a silly question.
• Remove approvals and process to the absolute minimum

you need: This is really about trust. I’ve implemented
both zero approval budgets where complete trust is
provided and, as I write this, have just implemented a
£100 limit for a new learning budget we’ve launched
(as a compromise with a view to removing all approvals
once we show it’s being used the way we intended).
The zero approval budget was designed to build trust
with our people. We trust you to identify, invest in, and
complete professional development activities without
the police watching. Does it mean that someone
bought an iPad once as a “learning activity” and we had
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to arrange for a return and refund… admittedly, yes.

But it also meant over 5,000 other orders were placed
that were completely in line with our guidelines. And
that statistic is worth way more to the business than
the 1%-er.
• Share share share share share: Learning is infectious, so

whether it’s through specific forums or communication
channels, or built into a tech platform you’re using for
learning budgets, create a space where the team can
share what they’re learning, or hoping to learn, and
nurture that curiosity and community.
Parental Leave
Those who’ve worked with me in the past know this is something I have
quite passionate views on. The current state of play will differ by country,
but I’ll broadly generalize as statutory leave provisions that do not reflect
modern families, and company parental leave policies where parents have
to put a few hours aside to work out what they can and can’t do. I’m not
a parent and probably won’t be, and admittedly I have worked on my fair
share of traditional leave policies and believed the reasons around me why
a parent can’t access it in their first 12 months, or if they don’t return for 12
months, they have to pay it back.
What changed my perspective were the very people it set out to
support. Parents. The more time I spent with parents, the more I realized
it was a company policy designed for the company, not for the parents.
I would speak with mothers who had delayed a decision to start a family
because they weren’t entitled to leave yet. I spoke with fathers who
desperately wanted to spend time with their new family addition and
were told they get a week off or need to take all of their PTO. And I spoke
with same-sex, single parent, and adoption-based families who struggled
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to navigate policies that were never designed with them in mind. An

overwhelming pattern I found across all parents, regardless of gender,
circumstance, or location, was the need for parental leave to provide
meaningful time with their new child.
Every company will have a different appetite around parental leave,
different statutory requirements by location, and different budget
constraints too. The baseline I have found myself coming back to in
multiple startups might be a helpful starting place to consider as you look
to engage and support your parents and would-be parents.
• Leave: Meaningful and fully paid. I’ve used 12, 16, and
26 weeks of fully paid leave at various companies and
also considered additional pro rata pay and the ability
to carve up that leave (i.e., 24 weeks at half pay rather
than 12 weeks at full pay might be a preference of some
parents).
• Gender-blind: There’s a shift from maternity/paternity/

adoption policies to primary and secondary caregiving
policies, and even further to gender-blind. I am in the
latter camp and making leave and support available
equally to all parents, regardless of both gender and
family circumstances.
• Global: Human beings love to compare and, if you’re a

global team, you’ll have folks looking across the fence
at what benefits are being offered elsewhere. Unless
there’s a really compelling reason why a parental leave
policy can’t scale globally, I’d highly encourage one
offering globally.
• Flexible: Not every family needs one or both parents

having big lumps of leave the way we think of parental
leave. Sometimes it makes sense for extended periods
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at a lesser entitlement, or the flexibility to stop and start

it. Being able to take the statutory minimum and then
having the flexibility to take chunks of leave within one
to two years rather than all at once can be super helpful
for people, especially if there are considerations around
caring arrangements.
• Accessible: My favorite one so I kept it to last. It’s

not easy getting everyone on board with this (I
certainly haven’t been successful every time), but
I fundamentally believe it’s the right thing to do.
Accessibility means removing the tenure requirement
and removing clawback provisions. Parents do not
need more barriers up against them and these are
risk-based policies that play to the 1% of people who
abuse the offering, not the 99% of people who do not.
Accessibility and autonomy are critical when a family
is expanding, and I count on one finger the number of
times it’s been taken advantage of (out of 50-ish, which
I guess makes it the 2% rule).
Pay Transparency
Pay transparency has been one of the most hotly debated issues in the
reward space in the last five years. The status quo for too long has been to
accept the power dynamic where employers have asymmetric information
and advantage to control a pay conversation. Between reward frameworks,
market data and benchmarks, budgets, and internal pay knowledge, it’s
a steep mountain for a candidate or employee to climb to reach a point
where they feel their pay is set with clarity, fairness, and reflective of their
experience and performance.
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There is no silver bullet to this, just a long line of candidates and

employees hoping for change. For a more level playing field. To start day
one confident, they are being recognized for what they bring, rather than
feeling a bit weary after a fight.
One of my favorite parts of startup life is the ability to experiment,
analyze the impact and results, and iterate. The ability to enact change
when there’s not a huge amount of embedded structure already isn’t easy,
but it’s easier than established organizations without the same freedom to
experiment and iterate. And, if the results are poor, the ability to roll back
the changes.
For this reason, I think startups are a fantastic place to explore the
concept of pay transparency and how we take it from a “nice to do”
concept for the most progressive organizations, to a “must-have” forming
part of every company’s social license to operate. In practice, it’ll probably
form part of a legal license to operate in most locations soon anyway.
On several occasions, I’ve shifted recruitment processes at startups to
include transparent salaries and benefits. For some roles like a People
Advisor, it means putting salary ranges like $70,000 to $80,000 on the
advertisement so that all candidates have that information before they
apply. For roles where variable compensation exists, it means putting
the total cash compensation like $60,000 to $65,000 plus $60,000 on-
target commission, or plus 10% bonus. For good measure, I’ll usually
ask for salary expectations, if they have them at this stage, as part of the
application. Note, this isn’t asking for salary history and there are enough
documented reasons now why we shouldn’t ever do that, but in this case
asking for expectations back makes the first stage for those who progress a
very informed conversation on both sides to check for alignment.
Pay transparency discussions bring out the best questions, so for the
rest of this lesson (that I’m still learning and implementing!), I wanted to
share some of the best questions to help get under the skin of the merits of
pay transparency.
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Will I miss out on applicants who don’t fall within that range?
Possibly, but it’s likely to be far outweighed by what you’ll receive through
transparency and there are ways you can prevent applicant leak at the
application stage. If a candidate’s expectations are less than the range
you’ve provided, they’ll self-calibrate and likely reset their expectations
in line with the range. It’s really hard for candidates to know how to price
themselves in the market so consider this a gift.
If a candidate’s expectations are higher than the range, you’ll see one
of two things happen. They’ll still apply and either make known in their
application that their expectations are higher, or just state expectations
are at the top end and wait to learn more about the role before sharing
their original expectations. Or they’ll choose not to apply because the pay
doesn’t meet what they’re looking for. This is OK for some candidates and
might show a misalignment between the level of the role and the level of
the candidate. A helpful tactic is that below your salary range, you can use
a statement like “If your salary expectations are above this range but you
think you’re a great fit, we’d love to see your application and discuss with
you your alignment to the role and what options we might have available
to make it work.” It’s possible there are other levers to pull around benefits,
equity, growth opportunities, etc.
What if the salaries are more than what we pay the current team
members in those roles?
This comes up more than I wish. The key here is why the salaries are
different. If the role is genuinely positioned higher in terms of the level
of experience and skills the expected employee will bring, that’s a very
valid reason for paying more than existing team members. The key here is
for the manager to be transparent about this before you go out to market
and address any questions. In my experience, their future teammates are
almost always very understanding of the reasons and just don’t want to
miss out on the opportunity to grow and increase their pay too.
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If the salary is higher because the market has moved and your pay
range has increased as a result, or if the existing team is below the current
market rate regardless of the reason, you have a more fundamental problem
than pay transparency. This points to an area of your reward framework or
cycle that hasn’t synced salaries with market rates quick enough to catch
up to market. It poses a choice. Do you include the pay range and risk
upsetting your current team, or do you hide the pay range and disadvantage
candidates applying for the role? If those are the only options you are willing
to consider, it doesn’t matter which one you choose. Both do damage,
although hiding the pay range is probably the less risky business decision to
avoid heightened risk of churn. Just know though, once a new person starts,
everyone in the team will eventually know the salaries of everyone else.
Transparency either happens by design, or by human behavior.
There is a third option, which is to tackle the more pressing issue to
enable pay transparency. There’s a rough and ready way to tackle it and a
more comprehensive way, so if time is a priority and you’re in “that” sort of
startup, rough and ready might be worth a look.
The rough and ready way is to make market adjustments for just
the team or roles directly impacted. If you’re hiring a Front End React
Developer, it means all Front End React Developers who are too far below
market based on the ranges you have. There is possibly a more systemic
problem affecting other teams, but the focus here is on fixing an issue you’ve
found and keeping the hiring engine going. Once the market adjustments
are in, you have the ability to share the pay transparently on the job ad and
continue on. Another way to look at this is this – if you discover your team
is paid below market, your competitors are going to be using the higher
salaries when they reach out to your team to pitch them opportunities. So
even if you hide salaries from the job advertisement, you’re opening up your
team to a significant reason why someone would take another opportunity
and leave. This is why it’s so important to lock your team in. There’s no point
focusing on hiring if there’s a revolving door within the team.
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The more comprehensive issue is to go back to the framework and

cadence for reviews to see where it slipped out, and assess possible
impacts across other teams too. These sort of things happen all the time
throughout reward cycles, so we need to be comfortable with iterating. In
the example with the developer earlier, if you’ve rectified that team, the
review of other teams can happen simultaneously and should probably
start with the highest risk areas of the business (those in hyper-growth
mode or those that have skills identified as in shortage in the market).
How big of a range can I put on the job advertisement?

When pay transparency laws started to be passed through a number of
US states after the pandemic, we saw the rise of pointless transparency.
Companies, being forced to now comply with pay transparency laws,
choose to set the range so large as to be pointless and of no benefit. I
remember one infamous one for a software engineer where the range was
$500,000 wide. Pointless and a waste of everyone’s time.
Admittedly, there are some roles where the range can be difficult to
keep narrow especially if you’re setting a total compensation range and
including things like variable compensation, commission, and the value
of equity grants. If you’re advertising across multiple geographies and set
pay based on the local market, including a single range, covering multiple
geographies will also usually mean a very wide salary range.
As a rule of thumb, if I’m only posting base salary on the advertisement
and in a single market, I aim to not exceed a 20% range. A bit of creep isn’t
harmful, but when we start seeing advertisements for $60,000 to $120,000
for roles, no candidate is looking at that and feeling informed or impressed.
Where advertisements cross multiple markets, make it transparent
that this is the reason for the discrepancy, and use a location at either
end of the scale to help people understand where they can likely position
themselves. Again, without this sort of detail attached to the salary
ranges, it’s near impossible for candidates to consider if it meets their
expectations.
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And finally, where multiple compensation components are included,

don’t just lump it together into a huge range. There’s a huge difference for
a sales rep seeing an advertisement saying $120,000 OTE compared to one
that says $80,000 base salary plus $40,000 OTE commission. Split out the
components so candidates can understand what’s on offer and make an
informed decision on whether they are throwing their hat in the ring.
What about transparency of the current team’s salaries?

This is an area of pay transparency that is truly fascinating, and muddled
up in sorts of human behavior and personality too. One approach that
some companies have taken is to take pay transparency to the maximum
level possible and publish the salaries of their team either internally or
externally, or both. The question has come up from the team a few times in
startups I’ve been part of, and for me, the reasoning behind it can be really
helpful to understand.
“I want to know if I’m fairly paid compared to others?”

“If we’re trying to be more transparent, why wouldn’t be just
be transparent about this?”
“You can’t fix what is hiding in the shadows.”
There’s a lot tied up in that sort of reasoning, and all things I’ve heard
as part of why you’d take transparency to that level. It was also coupled
with counter opinions around people feeling uncomfortable having their
own salaries being shared, and people not wanting to know salaries of
others too, all of which is also a consideration.
I have no doubt there are some businesses who have infused a radical
level of transparency into their culture from day one. This level of salary
transparency makes a lot more sense when done from the start, as it then
represents the business that every future new joiner has chosen to be
part of. I’ve never been able to rationalize, on a personal level, how the
preference of one person to have public salaries is more or less important
than another person’s preference to not have public salaries, unless there’s
an opt-in where people can choose to share their own only.
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There aren’t too many lessons in this book where I don’t share a
strong opinion, even loosely held ones, but this one fits into the bucket
of things I feel conflicted and undecided on. The test I want to now apply
the next opportunity I have is if you have a robust salary, role, and leveling
framework across the business and make it transparent around what roles
exist, what is expected of each role at each level, and the salary ranges the
business have set for each role and level, is the rationale for public salaries
still there, or has it diluted because transparency of design and decisions
has fulfilled some of the original concerns?
The “Pay Me More or I’ll Leave” Ultimatum

It’s a people issue we never want to happen, but we’ve all probably had it a
few times. A team member asks to speak with you, has an offer on the table
at another company, and is using it to negotiate a pay rise.
I received an unexpected but very real insight into how we end up
in this situation from a friend and former colleague. We’ll call her Sam.
Sam’s story isn’t something that happens every time, but sometimes in
the People space, we can feel attacked by these ultimatums and feel a bit
bitter. I’ve certainly been guilty of that. So I like Sam’s story for a number of
reasons, as you’ll soon see.
Sam had tried to have a conversation with her manager about pay on
the basis of her performance and having not had an increase in almost
two years. Sam’s manager had said to her that she needed to back up the
request with data to prove why a pay increase was appropriate (I’m not
going to tackle this problem, but you’re probably thinking the same thing
I am about the manager at this point). Sam pulled together as much as
she could around what she had delivered, and also grabbed a few salaries
from Glassdoor as a comparison. She went back to her manager, but no
luck. This time, the manager said the Glassdoor salaries don’t justify the
pay rise but her performance had been strong and she’ll be considered
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for a pay rise at the end of the year which was still over six months
away. Sam enquired about bringing forward the pay rise and was told
only exceptional cases are considered by the HR team and this wasn’t
exceptional.
So, Sam started looking elsewhere and ended up with two job offers
(Go Sam!). She didn’t really want to leave but she would if she felt her
performance wasn’t reflected in her pay. Sam spoke with her manager
again, this time referencing two offers and asking for it to be raised as an
exceptional case for review. She was then invited to a meeting with the HR
Business Partner and was told they don’t respond nicely to ultimatums,
that her pay wouldn’t change, and if that meant she will resign, then it
would be a shame. There was also some guilt-tripping from the HRBP
about how the workload for the rest of the team would increase if she left
but I’m parking this under HR behaviors I wish would die quickly. Sam
resigned and is now earning more money elsewhere and, last I checked, is
really enjoying her role and team too.
I really felt for Sam through this process. She kept having barriers
put in front of her and ended up using the ultimatum as a last effort to
show how serious of an issue it was for her. The going belief in the HR
and People profession is to not give in to ultimatums as they’ll probably
leave anyway. Some people probably do. But some don’t. And it’s our job
to navigate the scenario enough to understand what sort of judgment we
apply to this, rather than the blanket approach to not give in. I know I’ve
fallen into this trap, and there are a couple of ultimatum conversations
in the past that I wish I could replay, and a few tips and lessons I’ve
swallowed along the way.
Mitigate the Likelihood of Ultimatums

I’m a big believer in the concept of stickiness. Identifying and investing
in the reasons for each individual that makes the business a very sticky
fit for them. When the stickiness wears off, it opens up the risk that they
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find a stickier fit elsewhere. In the case of ultimatums, our first priority
should be to reduce the likelihood someone feels that their pay doesn’t
reflect their role and performance. This means regular reviews of roles,
performance, and pay, a clear link between someone’s performance and
achievements and pay increases, a close eye on external conditions that
affect cost of living, and perhaps most importantly, coaching managers
to have proactive and candid discussions with their team members
about pay.
When We Get Pay Wrong

Some ultimatums are because we simply got it wrong. We’ve let our
team member down, either through not keeping up with the market
or not ensuring their performance, skills, and contribution to the team
are reflected in their pay. When these ultimatums happen, there’s
an opportunity for us to make it right, but it’s important to do that
sensitively too and consider the full picture. If it’s clear that we got it
wrong and we’d like to try and make it right, it’s worth asking your team
member if there are any other things on their mind that would improve
their experience at the company. It could be growth opportunities,
relationships within the team, feedback, recognition, training, tools,
and the list goes on. The reason why this is important is that if the belief
around quick turnover after agreeing to new pay is true, the reason
why they leave is less likely to be pay rather than something else. Sure,
it’s possible a competitor puts a massive offer on the table and they
accept, but that’s an uncontrollable factor. Typically, quick turnover
after negotiating a new pay is because something else has prevented
stickiness, so you may as well know about it now and work through it
than find out later.
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When We Don’t Get Pay Wrong

The scenario earlier of a competitor tabling a massive offer is a good
example of this. Some ultimatums are simply out of reach, either because
the other offer is well outside of the reward framework that there genuinely
isn’t a budget available for it, or it risks severe disparity with the rest of the
team (i.e., don’t create another problem by solving a problem). When this
plays out, the situation can feel more complex and the risk of churn much
higher. I’ve had this a couple of times, and it’s not uncommon in tech
companies for some mammoth competitor offers to lure away in-demand
skills. This is typically where I don’t agree to the ultimatum and accept
we’ve lost someone, but it’s not the starting point. In these situations, it’s
worth exploring how they’re feeling about other parts of their role, such
as the stickiness factors we discussed earlier, and if you were to table
something that gets you part of the way there and consider changes in
other items raised, whether they’d be open to considering this.
I cannot stress this “watch it” enough. Team pay parity is sacred and
should be nurtured. It doesn’t mean things need to be equal, because they
shouldn’t be, but parity of reward outcomes that are transparent, with clear
links to performance, and building a sense of trust and fairness within the
team. Team parity should almost always outweigh individual outcomes.
The Law Is the Floor

When I was studying for my HR qualification and throughout my first few
years in the field, I was under the impression that the laws in each country
determined what people received by way of benefits. If we’re only talking
about legal entitlement, then indeed they do. But in many countries, the
statutory entitlements under law leave a lot to desire. It’s what you have to
do, not what you should do.
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If you’re a global startup, it also means you’re keeping an eye on

the laws of all countries you’re operating in and navigating the need for
compliance and consistency. It wasn’t until I entered a global environment
that it became more obvious of the need for us to have a global position
on benefits designed for our startup and consistent across the team. Take
something like maternity leave. Depending on the country, statutory
maternity leave can vary from unpaid leave only to six months’ leave at
full pay, to twelve months leave at statutory pay rates. Navigating all of that
individually is complexity that your People teams and managers simply
don’t need.
The way I’ve tried to look at the law is as the bare minimum you
must do. The law is the floor. And there are actually very few statutory
entitlements that you’d argue are best practices in themselves.
All Benefits Are for Day 1

The hiring manager calls you after a final stage interview and offers you
the role. You’re over the moon. They share with you how impressed they
are and excited by what you’ll bring to the team. You turn up on day one,
pumped to start onboarding, and get stuck in. You finalize all of your
payroll forms and start reading up on benefits.
You need to work here for three months before you can enroll in
retirement benefits. Three months before you can access your learning
budget. Six months before life insurance cover kicks in. Your probation
period before you’re eligible for a bonus. Twelve months before you can
access parental leave benefits. For a company so excited by what I’ll bring
to the table, they seem to be hedging a lot of bets if things don’t work out.
You sit back in your chair, curious as to why they are confident enough to
offer you a job and pay your wage, but not so confident as to give you the
full package until you’ve hit a certain timeline.
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The tenure requirements we’ve put in place around benefits are a

total misfire. Remember the 99% lesson from earlier in this chapter? This
is a prime example with some unfortunate side effects. When new team
members come in, they are already eager to impress, and likely a bit
anxious and cautious too. We need to be doubling down on our support of,
and confidence in, them to succeed and achieve. Trying to mitigate some
admin or a bit of cost if things don’t work out sends the opposite symbol.
It says we aren’t yet confident in you to receive access to everything. We
have to go all in on our new team members, which means all benefits
from Day 1.
ou Probably Won’t Retire Early Because

Y
of Equity
We need to talk about equity. If I do a second edition of this book in the
future, we’re going to split out equity into its own chapter as it’s quickly
becoming one of the most complex parts of startup compensation to
navigate. Some companies nail it. But most I’ve come across struggle to
get it right. I’ve seen a fair number of share and option frameworks to date,
and I can’t say any of them truly nail it. It’s become a personal endeavor to
keep iterating and finding ways for equity to play the role it can in people’s
experience.
One of my first ever introductions to the world of startup equity was
from a friend who told me the plan was to exit in a few years and retire. My
first thought was “Hell yeah!”. At the time, he was an employee at a seed-
stage startup and took a sizable haircut to his previous compensation to
take a meaningful equity stake. An all too common story, and a decision I
wholeheartedly support and respect from anyone wanting to get stuck into
building while the startup is still a garage band.
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It turns out he took a 0.5% equity stake and, in his mind, he would
sell it in the future when the company became a unicorn (i.e. worth
$1 billion). “I can live off that for the rest of my life.” It didn’t click at the
time because I was a novice in the world of startup equity. Like 99.5%
of other startup employees, my understanding of equity didn’t extend
beyond understanding the general concept of shares and options, and
that if the company is sold or listed in the future, I could get a payout.
What my friend experienced was equity hype. A combination of the
leaders of his startup allowing unrealistic expectations and an excitable
recipient who started believing, even planning for, the best possible
financial outcome that might just come from an exit.
Over the course of several startups and now over a hundred
conversations with startup employees about equity, I’ve ended up with a
long list of things I’ve had to learn along the way and, in some cases, have a
brutal reality check on. Here are some of the most pertinent.
E quity Requires a Framework More

Sophisticated Than What We Use for Salaries
In the early days of a startup, founders and investors are likely picking
and choosing people to receive equity grants. It’s usually a mixture of
early-stage employees (very common up until 20 or 30 people given
cash constraints) and others they want to recognize and retain. It’s not
uncommon for this to be very unstructured. Discretionary decisions,
discretionary allocations, sometimes even discretionary terms of the
agreement depending on what the relevant equity scheme allows for.
As the startup grows, greater consideration is given to the size of the
equity pool by shareholders and investors, especially if the startup is
investor-backed and likely to go through rounds of funding in the future.
The equity pool is an agreed allocation of a percentage of the company
for employee grants and can be dilutive to existing shareholders. Over
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time, and as the cap table changes, the equity pool is revisited and
sometimes resized to take into account future headcount growth and new
employee grants.
At the same time as this, the startup is growing into a scale-up
environment. Roles are becoming more specialized and defined, teams
are starting to take shape and consider their own structure and operations,
and the People team (hopefully in place by now) are looking at the
infrastructure needed to grow, such as scalable reward frameworks,
performance management, engagement and feedback mechanisms, and
progression. These changes to both the governance and operations of
the startup, and the headcount growth, both call for a more sophisticated
approach to equity in the same way we’d be maturing the approach to
compensation or other areas.
The reason equity requires a more sophisticated framework than we
might be hoping for is how fluid the equity environment is. Valuations
may go up and down over time. Early-stage employees often receive larger
equity grants than later-stage employees. And it can be difficult to quantify
the value of equity you’re awarding on a consistent basis. An employee
receiving 100 shares at a $10 share price is the same value of equity as
someone who joins and receives 50 shares when it’s a $20 share price, but
at that stage the value of the first employee’s equity has doubled.
There are four scenarios I try to make sure are built into equity
frameworks to allow for the majority of considerations as we grow. More
recently, I’ve found answering these four scenarios will flesh out a lot
of the thought and consideration required when building an allocation
framework.
1. New hires: What do we award by role, level, and

geography and have we modeled the one- and
two-year growth plans and headcount against the
framework and equity pool?
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2. High performance: How do we use additional equity

grants to reward high-performing team members
and build more stickiness? Similarly, if high
performers take on more responsibility and bigger
roles, there may be equity implications too.
3. Tenure/retention: This may be more or less important

depending on how equity vests and how it can be
exercised. But if you’re running the standard four-
year vesting and one-year cliff model, how do we top
up those when vesting ends to ensure there is always
equity continuing to vest (i.e., stickiness again!)?
4. Leavers: How do we deal with leavers taking into

account equity pool sizing, the need and ability to
exercise, and sometimes the tax implications in the
employment country?
Understand the Risk and Likelihood of Dilution

If you’re in a startup without investors or a need to fundraise, this may be
of less consequence to you, and it’s probably another huge selling point to
the value of bootstrapped businesses who don’t nearly feature enough in
the technology press. If you’re in an investor-backed startup with equity
and have fundraising on the horizon, you need to understand dilution.
If you haven’t come across dilution before, it’s essentially the process
where the percentage of shares you own decreases as a result of new shares
being issued. So let’s use the preceding example again.
• There are 1,000 shares in the startup, with a share price

of $10 per share, making the startup valued at $10,000.
• You receive 100 shares which puts the value of your

equity at $1,000.
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• This means you own 10% of the equity in the company.
• Your startup does well and decides to take on a round

of funding to fuel the next stage of growth. An investor
purchases 200 shares at a share price of $20 each,
making a total investment of $4,000. Unless existing
shares are being sold, these are often added as new
shares (see the next note on preferences).
• There are now two things you should be aware of:
• A share price of $20 each means your equity is now

worth $2,000 instead of $1,000.
• There are now 1,200 shares in the startup (the original

1,000 plus the 200 shares from the investment). This
means 100 shares now represents 8.3% of the equity
in the company instead of 10%. This is dilution.
Dilution is very common with startup equity and something to

understand, rather than to fear. The reason it makes this list though is
twofold: Firstly, my friend who received 0.5% equity as an early-stage
employee almost certainly won’t have 0.5% equity if they “become a unicorn
in a few years”, unless they’re in a true outlier startup. If you assume an
average of 15-20% dilution over four rounds of funding, it’ll be more like
0.2%. That would still be a load of money and congrats to anyone in that
situation, but it’s worth being mindful how dilution impacts you. Secondly,
dilution feels less important when businesses are growing very successfully.
In the example earlier, having 8.3% equity is quickly overshadowed by
knowing the value of your equity doubled to $2,000. This is the trade-off
considered acceptable for dilution. You can dilute the ownership percentage
of shareholders but return a multiple of that in increased share value. Where
a business is not growing successfully though, dilution can have a negative
effect. Imagine the company earlier raising money at the same share price of
$10. The value of your equity is the same, but the dilution still exists.
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Liquidation Preference
When an investor or new shareholder comes on board, they may have a
liquidation preference or preference shares. This means there is an order,
and sometimes a value, determined for where proceeds of an investment
go first. Those with liquidation preference will essentially get their money
back before those without preference. In some occasions, it can even be a
multiple of their investment depending on the terms agreed.
Again, this may feel less consequential if a startup is growing really
well and there’s a successful exit of some sort. What is helpful to know is
that employee equity is typically for ordinary shares and therefore at the
bottom of the ladder. A lot of other people will be paid first, and depending
on the preference terms, how many different levels of preference exist, and
the valuation of the company, the proceeds that make its way to ordinary
shares can be less than expected, and even zero.
E quity Is Worth Nothing, Until It’s

Worth Something
Sounds more philosophical than I mean it. Equity is not cash, or even a
bonus. It doesn’t pay the bills. You can’t take an option grant into the bank
to use it as a deposit on a mortgage. There is zero guarantee that the value
of the shares in your agreement is worth more than the paper it’s written
on. I’m sorry to pop the balloon, but it’s time for a reset.
Equity is a really memorable and valued thing to receive as a startup
employee. It allows future success to be shared. It might even start to
make you feel a greater sense of ownership over results, or think through
problems and opportunities in different ways. I hope that everyone who
receives equity either has it structured to allow for exercise and sale
processes to happen in a way that the employee sees value to their equity,
or gets to experience an exit event of some sort where the full proceeds
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are realized. The reality, however, is that very few people see either of
these things in a startup. Some do, and their stories tend to spread and be
shared. But most don’t see any value to their equity for a variety of reasons.
So if you’re holding on to a share or option agreement, I truly hope you see
value from it, but it’s important to make sure you’re comfortable with the
fact it may never happen.
Minimum Leave, Not Unlimited Leave

If you were on LinkedIn around 2016 and scrolling down your feed, you
would have been met every second or third scroll with another company
posting about how they’ve given their team unlimited holiday leave. To
date, it’s certainly become more common than other initiatives having
their time in the spotlight. Unlimited holiday is a pretty interesting
concept. The first time I heard of it, I cheekily asked if I could take the
whole year off because I had unlimited holiday.
Now, before I take aim at unlimited holiday, I really do like the
rethinking of holiday leave to be built around concepts of wellbeing and
trust, rather than leave entitlements. The thinking behind it is centered in
creating a great people experience, so big kudos to those thinking this way.
On paper, unlimited holiday is exactly that. We ask for our team to take
time off when they need it, communicate well with the team, contribute
to team planning and coverage, and not feel the pressure that comes with
an annual holiday entitlement. In practice, unlimited holiday means we’re
OK with you taking a bit more than what you’ve come to expect as your
entitlement, but not so much that we think you’re abusing the benefit.
The only difference with the latter is you’ve now moved the responsibility
and pressure of knowing what is acceptable and what isn’t acceptable to
your team member. It’s up to them to work out the norms and restrictions,
which usually don’t become explicit until someone steps on the wrong
side of what is acceptable.
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There’s enough research now into unlimited holiday to suggest that, on

average, people take less holiday than what they did when they had a clear
entitlement. Which makes sense given the pressure has shifted and most
team members don’t want to do wrong by their manager or their team.
This behavioral impact is merely a hiccup, and I don’t think the merits of
unlimited leave are lost. The principle of trusting the team to look after
their wellbeing and take time as needed is exactly what we want within
more workplaces. But without some sort of guideline to what is expected,
it’s hard for this to eventuate.
For me, I’ve landed on a reframe of unlimited leave to something that
aims to balance the principle of trust, alongside creating safety for people
to be trusted to look after their wellbeing. It involves setting the minimum
and maximum for leave. The minimum might be company policy or a
statutory requirement, so let’s say it’s 20 days. And the maximum is what
we actually accept before we start to think someone isn’t working enough.
So let’s say 40 days. The new holiday leave policy becomes “We offer up
to 40 days of holiday leave, with a minimum of 20 days each year to make
sure you’re recharging enough” or something similar. I think that means
we can’t call it unlimited holiday anymore which takes some shine from it,
but I’m OK with that!
This chapter likely felt heavier than other ones which is to be expected
given the complexity and sensitivity of reward. In the next two chapters,
I’m sharing principles and lessons learned in Learning and Performance,
two parts to the People experience that go hand in hand in terms of
developing our people, but require their own techniques and approach.
Summary
1. Build benefits for the 99% of people who will benefit
from and value them, rather than the 1% that
abuse them.
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2. The status quo of hiring without pay transparency

has passed its expiry date. We need to prevent
asymmetric information and an employer-dominated
power dynamic, and reduce the inequities in pay
discussions that prevent our people from feeling
recognized, valued, and fairly treated.
3. It is not black and white to simply say no when

someone poses the “pay me more or I’ll leave”
ultimatum. There are reasons why it’s sensible
to counteroffer and scenarios where it doesn’t
make sense, but primarily our goal is to reduce the
likelihood from it happening in the first place.
4. Our statutory obligations for benefits and leave are

not our benchmarks for good practice. They are the
bare minimum we have to do and there’s almost
never a compelling reason why we’d ever want to
only do the bare minimum for our people. Similarly,
to instill trust into the relationship with new joiners
early, avoid tenure restrictions on benefit eligibility.
5. We need to bridge the knowledge gap on all things

equity, setting realistic expectations, communicating
the key components of equity, and allowing
our people to have access to a transparent and
meaningful way to share in the business’ success.
6. Unlimited leave may seem sexy, but it often proves

to have a negative effect. If you do want to rethink
leave entitlements, at the very least, it should have
a minimum amount of leave that allows for both
adequate well-being rests and meets any regional
requirements.
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CHAPTER 7
Learning
This chapter continues our exploration of key components or milestones
that allow us to engage, develop, empower, and recognize our people.
Learning is undoubtedly one of the biggest reasons why people join
startups, especially if they are transitioning out of bigger and more
established businesses. But learning doesn’t just happen in startups.
It takes a whole lot of planning, feedback, design, onboarding, and
leadership support to enable learning and the growth culture associated
with it, which is what we’re going to dive straight into.
Water Your Plants

“We don’t really do much formally by way of learning and progression
because we’re a startup.” Yawn. We’ve all heard it. I’ve even said it a few
times. The excuse wears thin quickly and it’s detrimental to everyone
in the team. In what is becoming a real theme throughout each chapter,
half the trick in startups is knowing when to build out a part of the people
infrastructure and how to make sure it’s aligned to the stage of the business
and the performance and objectives of the business.
I’ve always been curious about the return a startup receives from
investing in the learning space. It feels intuitive, but I can’t shake some
skepticism. I can throw thousands of dollars, and I do, at learning budgets
and watch as people buy books and subscribe to online courses, but should
I be thinking of those thousands of dollars as an investment that pays back

Chapter 7 Learning
(and how would I know that), or just treat it as a benefit (which also pays
back in its own way, but for the purpose of this I’ll treat it as spend in a simple
form). Similarly, I’ve taken part in week-long leadership summits where I sit
in a classroom and take in a whole bunch of content and set plans for how I
will use it. Oh, and don’t forget the role-plays. They probably cost between
10k and 15k a pop, and outside of the connections and relationships, I can’t
for the life of me tell you something specific that I did differently in the
workplace and the impact that has on my or the business’ performance.
Each time I’ve joined a startup, there are parts of learning that always
make it on to the road map. Onboarding, progression frameworks, manager
development, technical training, and the list goes on. All important stuff. But
the more I work on learning programs and initiatives, the more I find myself
thinking about goals and outcomes. The ultimate goals and outcomes.
Because I don’t think any of those learning initiatives are actually the goal,
but rather the tool or enabler for what we’re actually looking for. When I
sit in exec or board conversations, very rarely do we talk about learning
specifically. We’re talking about productivity, culture, engagement, retention,
and preparation for our next stage of growth. That’s more indicative of the
outcomes we need rather than what learning quickly becomes, which is a
series of completed projects and some feedback surveys.
With this in mind, there are some common pillars that seem to sit in
between what we do in the learning space and the sort of outcomes we’re
trying to achieve. This is not a playbook, or even a recommendation. It’s
just an observation after a few startups and even in larger organizations for
the things I tend to look for and focus on in the learning space when there’s
very little in place already.
Growth Culture
In the next chapter, I’m going to cover the concept of startups and team
members outgrowing each other. It could easily go in this chapter too, but
I think the link with performance is punchier. As companies rapidly grow
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and try to scale, they start to transform and need to rethink a lot of how
they operate. Hiroshi Mikitani’s Rule of 3 and 10 has always resonated
with me – essentially that everything breaks and needs reinventing
as companies go from 3 to 10 to 30 to 100 to 300 to 1,000. In startups
going through early-stage funding, you’re likely going to see three or
four transformations of the organization in a short space of time. It puts
pressure on people to be agile, resilient, flexible, and curious. And it is
that specific need to allow people to grow with the organization that I find
myself honing in on constantly for how we nurture and develop it.
I mentioned learning budgets before and understanding the return
on that spend. So it feels natural to now revisit that with a different lens.
In three consecutive startups, I’ve introduced learning budgets with
some very specific traits around accessibility, community, and trust.
I would never argue with someone about the individual return we get
on an employee reading a book. But what about an entire product and
engineering team using their learning budgets on resources, with time in
their work day set aside for learning, recommendations flowing between
team members on what they’re learning and what they’ve enjoyed, and
managers finding opportunities for them to apply some of the things they
were learning about. There’s no price to that, but it’s quite the return. It
builds a sense of curiosity, the feeling we’re all continuously learning
and trying new things, and a sense of community within the team. All
things that are incredibly helpful when we hit the “Rule of 3 and 10”
transformations.
Great Managers
Tightly coupled with a growth culture are great managers. Managers
have a heightened ability to enable or disable their team on every single
outcome we previously discussed. They cast a shadow deep into their team
structures and even across teams, so if the behaviors and capability are not
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aligned with the culture, engagement, retention, productivity, and future-

proofing needed within the business, it’ll feel like inflating a balloon with
holes in it.
The first step is understanding what great managers look like in each
specific business, and even within teams as there can be differences,
especially if you compare commercial and tech teams. Some managers
will self-assess thoroughly, but there’s some top-down thinking around
behaviors in particular that needs input, and some bottom-up thinking
from team members around how managers can set them up, individually,
for success.
There’s a lot of theory out there, but managers are not developed
through theory and content. No one ever walked into a workshop and
walked out an expert. So I like to think of the content as a prompt. A little
nugget or resource that tickles the curiosity of the manager, or a future
manager wanting to explore, and helps them take the step to trying new
behaviors. And once they do take that step, a whole lot of reinforcement,
coaching, and safety to explore how they show up as a manager and how
they contribute to what the business is trying to achieve. Everyone wants to
be a manager until they are one, because it’s harder than it looks and you
never feel capable enough.
Onboarding
I guess this one might feel like a strange addition given my reticence to
specific learning initiatives. Onboarding gets a free pass through that. Not
because we don’t want to create an amazing and personalized onboarding
experience for new joiners, but because of its unique influence on
productivity, engagement, and turnover.
Most of the startups I’ve worked in have been B2B SaaS startups. And
one particular onboarding challenge rears its head in every single startup.
It’s hot on the lips of founders, it’s tested and analyzed by investors,
and it has a direct link with the revenue growth of the company. Sales
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onboarding. The period of time from which someone joins the sales
team to the point they are considered fully ramped and productive. It’s
one of the biggest risk areas during hyper-growth as to whether a startup
has enough ramped capacity to meet its next revenue objective, and
depending on the complexity of the product and the sales cycle, the
onboarding process can be quite extensive.
I’ve picked sales onboarding as a specific part of onboarding not as an
anomaly, but rather a really helpful and effective place to start. Onboarding
itself has a clearer connection than many other learning initiatives to
business outcomes, particularly productivity and having the right talent
performing well at every stage of the startup’s growth journey. It’s also a
risk area for other areas. Poor onboarding leaves a stench on engagement,
which is a great test of culture and team support, and there’s ample
research for the heightened risk of turnover in the first six or twelve months
of employment. If we nail onboarding, the positive effects compound and
feed into the talent, performance, and progression areas too.
L earning Is About Experiences, Not

Just Knowledge
A few years back, I shared a post on LinkedIn that hit a spot with a lot of
people. It went like this:
Things we do and realize later didn’t teach us much:

–– Online courses
–– Conferences
–– Sit in a classroom
–– Most networking
–– Read books
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Things we do and realize later taught us heaps:

–– Work on stuff we’ve never done before
–– Practice our craft in different contexts
–– Be mentored by someone
–– Fail miserably at something
–– Have a difficult conversation with someone
–– Volunteering
–– Work for a bad manager
I remember what prompted the post very clearly. It was a series of

conversations with people at all levels in the startup I was part of at the
time where we were discussing learning. There was a theme throughout
these conversations, and after the theme started emerging, it was one I was
keen to provoke and test with others to see how far the theme continued.
The discussions related to how we learn, both as humans and also in
our roles. The team member reflecting on transitioning from a large and
highly structured organization to a scrappy startup and the opportunities
and challenges it has provided them. The manager who told me how
some of the challenges within their team had really helped them reflect
on their leadership style and show them how small tweaks to their style
could influence different outcomes. The team member who was telling
me about their recent volunteering shifts and how much perspective it’s
given them on their own life and upbringing. The senior leader who shared
several mistakes they had made at a previous company and some of the
things they were going to change or be mindful of at our startup when we
approached a similar stage.
All of these reflections, plus several others, all touched on things that
we realize had an impact on us as humans and as professionals. Situations
where, at the time, we probably didn’t realize the extent of our learning.
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But in hindsight, these situations made for critical learning milestones

that influence how we now behave and perceive things. No one talked
about the self-help book they read. Or the conference they went to. Or
the online training they were forced to do. It’s not to say we don’t learn
something from these and they still play an important part. But if our
approach to learning doesn’t extend beyond the traditional knowledge
buckets of courses, books, and conferences, we’re only tackling a tiny part
of someone’s learning experience.
So the next time we’re considering how we can help prepare a high-
performing individual contributor for their first manager role, let’s not just
stop at some training. Maybe they could start to pair with a manager as
part of conversations and observe what they liked and what they would do
differently. Maybe they could start with a junior team member for a short-
term project where they take on the manager role and have a chance to
experience that before they step into a manager role formally. And once
they do take on a manager role, the learning can’t and won’t stop. They will
need to experience the mistakes and failures that come with any new role
and have safety to explore these and learn from them.
The “Best” Career Advice I Ever Received

“If you want to progress your career, do your job well.”
This is definitely the book equivalent of a clickbait title. This isn’t the
best career advice I ever received. But it’s by far the most memorable. It
was much earlier in my career that it was shared with me and it’s taught
me heaps, in its own way.
I’ll start with the obvious, which is the stupidity of the notion that
to progress your career, you just need to do your job well. That’s not the
experience of most people, and frankly, it hasn’t been my experience
either. It also reads as a stereotype for someone asking their manager for
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a promotion and being told the “keep working hard and we’ll think about
it” excuse. I should also point out at this point that while progression and
promotion don’t mean the same thing and I’ll cover that off shortly, the
context in which this advice was given to me was relating to whether I
would be promoted.
The reason why it’s memorable is because of what I’ve taken away from
it and how impactful it’s become for me. Whether it was ever intended this
way I have no idea, but I don’t imagine the giver of this advice might have
anticipated the tangents would take it on in the years ahead. And some of
these tangents, well, are pretty loose.
Do I Even Want to Progress?

Why is everyone obsessed with promotions?
Will I still be seen as doing well if I’m just content in my cur-
rent role?
What if I don’t know what I want?
All questions I have asked myself a number of times, and I don’t

imagine I’m the only one who might feel this way. We have a tendency
to assume progress and growth equals promotions. Sometimes it does,
but in several of my roles I’ve not had any real desire for promotion. Most
of my promotions have… just kind of happened. I have a desire to be
good at what I do, and to keep getting better. I have a desire to positively
impact people and the world. I have a desire to see my pay increase (who
doesn’t?). And I’d say all of these things feel like progress for me. And all of
them can happen without promotions.
So the conversation I need to have with myself, and my managers,
isn’t really one of progress the way we typically define it. It’s one of growth.
What can I do, and what support and environment do I need, to grow in
my role? What experiences do I really want to have even if I suck at them
or dislike them? What is going to get me out of bed on a Monday morning
thinking “let’s get it!”?
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Similarly, the conversations and systems I need to be encouraging

as a member of a People team need to reflect the diversity of progress
also. It needs to be deeper than a framework of roles and responsibilities,
even though for some that will be very important. And we need to make
sure that growth is incentivized and recognized, even if a role change
doesn’t happen.
Underperformers Are Rarely Promoted

I originally wrote this as “never promoted,” before realizing that we
all know someone who got a promotion that was clearly unrelated to
performance. So I’ll try to be more factual and have edited it to “rarely”
instead. This is probably the closest tangent to how the original advice was
intended, which is to remind myself that if I do want to push and make a
case for a promotion, it must be widely understood that I’m performing
well in my current role. There can’t be any doubt in the decision-makers’
minds that I’m ready to graduate.
The follow-on from this if a promotion does happen is that
underperformers sometimes don’t last long in their promoted roles.
There are many reasons why this might come about. If someone hasn’t
been set up for success, or provided the right level of support, or made
the full transition to the new responsibilities, it’s not uncommon for
their performance to drop off a cliff. The risk is higher once someone is
promoted. It’s a reminder that any time we step into a new role, we should
treat it as an entirely new job, just like if we joined a new company. It
means a version of onboarding, building role clarity, setting and agreeing
expectations, and making sure it is crystal clear for both us and our
managers what high performance looks like in the new role.
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hat Prompts a Manager to Say “You’re Ready

W
for a Promotion”?
When I reflect on promotions that I have done within my team, it’s never just
someone doing their current job well. That’s important, but it’s never the only
thing. It’s the same thing when I’m speaking with managers about promotions
in their team and their mindset to know if someone is ready or not.
There are three things that come up regularly that differ those who
are high performing and those who are high performing and ready for a
promotion or level up.
1. Outcomes: Performance is clearly articulated in

terms of outcomes and impacts. It’s not about effort
or inputs, but rather the results and business impact
as a result of their work.
2. Transition: Often, those receiving promotions have

already made some form of unofficial transition.
Even if it’s just an inch into the new role, they
typically have taken on responsibilities already that
are more reflective of the role they are going into. I
think this one drives a lot of the confidence managers
have when deciding someone is ready for promotion.
3. Making life easier: Our manager’s performance

is mostly a reflection of our performance, as
individuals and as a team. This is especially true
as teams grow beyond a couple of people. A key
contributor to promotions is often those people
who make life easier for the team, and therefore the
manager. Those that proactively identify issues, are
introspective to how the team performs and finding
ways to be more effective, and who help support
and amplify the team of others around them.
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Approach with Planning: Peer Feedback

Peer feedback can be a gift and a curse to someone’s development.
Rounding out feedback to provide a more holistic view of how someone is
performing and growing can be hugely beneficial and also helps to prevent
the impact of manager bias slipping in too. So when the feedback is
specific, meaningful, actionable, and nonjudgmental, the addition of peer
feedback can support both self-awareness and someone’s actions toward
development.
So, what’s the issue then? The risk of peer feedback is the
higher likelihood that it is not specific, meaningful, actionable, and
nonjudgmental, unless a significant amount of planning, upskilling, and
expectation-setting is completed. In my experience, it’s seldom devious,
but rather has a tendency to fall into a few traps that hinder it being useful
for the recipient. Here are a few things I’ve learned from implementing
peer feedback mechanisms.
Giving Feedback Is a Skill

It’s hard to provide feedback more meaningful than general praise. And we
often don’t really know the specific areas our peers are looking to focus on,
or the journey they’re going on too. It’s very common with peer feedback
for people to provide a list of general things they appreciate about
someone, such as them being a great team player or being happy to answer
questions for others, and if prompted to discuss how someone could
improve or where they should focus, we slip into “nothing comes to mind”
or “keep doing what you’re doing” feedback. For this reason, I try to invest
a lot of time up front helping people think through and structure feedback
based on specific observations, and discourage feedback for feedback
sake. It’s fine to not have any genuine feedback to contribute.
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Anonymous or Identifiable
Our peers will feel more comfortable if their feedback is anonymous
and taken into consideration by the manager, but this allows a greater
likelihood of “vent feedback,” which is the gripes someone has about
their peers under the guise of feedback around their performance. It
becomes a judgment on someone else, rather than something specific
for them to focus on. If feedback is identifiable, it will almost always be
overwhelmingly positive because, as human beings, we much prefer
to hold our tongue on anything not positive. I used to approach peer
feedback in the same way as engagement surveys – anonymous comments
rolled up into a report – but I think that was a misstep and dilutes how
effective it can be. I’ve since seen better results by managers identifying
a very small number of peers (two or three maximum) who have worked
closely with their team member, speaking to them first around the specific
areas of feedback that are seeking, allowing those peers to contribute this
feedback in an identifiable way to the manager, and the manager taking
that into account in their feedback conversation with the team member.
The Filter of Perception

I’ve had 360 feedback processes done where one comment will contradict
the next. It’s not that either of those comments are invalid or not real for
that person, but rather a symptom of how we perceive feedback. We put
our own individual filter and biases on the feedback we give and receive.
What we want to see more or less of in someone else is not automatically
true. It’s just our perception of it, and therefore input to how they might
think about that specific area of development. For managers, this means
helping people identify and place a filter on the feedback they give and
receive. Feedback is helpful to understand ourselves and those around us,
but not all feedback is equal and there’s an art to how we process and use
feedback to grow.
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T he Perfect Resignation: When the Time Is

Simply Right
My voluntary turnover target in any startup I work in is never zero. It feels
counterintuitive – while we know that involuntary turnover is unavoidable,
voluntary turnover is something we theoretically should aim to never
happen. If we build a truly sticky people experience, why would we want
someone to leave?
There is one scenario that gives me warm, fuzzy feelings inside and it
relates to resignations. It’s the person in our team who has aspirations to do
things that are simply not possible in our startup. It might be a passion to
make a difference in an industry that is vastly different from where they’re at
(e.g., transitioning out of FinTech into ClimateTech). It might be an increasing
entrepreneurial spirit that drives them to go and start their own business. Or
even, they’ve grown into a bigger role that doesn’t exist at our startup.
These are great reasons to leave a business, and something I believe as
leaders in startups we should be supporting and advocating for. You don’t
spend an entire career in a single startup, like you can in other industries
and in larger companies. The time we have people in our startup will come
to an end, so I like to think of the people experience as trying to make it
as sticky and fruitful as possible, and for our people to be well positioned
at the end of their time at the startup to take whatever next step they are
aiming for.
Don’t get me wrong, it will always feel bittersweet because I’m a selfish
person and someone leaving for however great a reason will still be a loss.
But when the time is right for someone to pursue something not possible
within a startup, it’s a perfect resignation.
In this chapter we’ve covered a number of parts to how we learn
and grow that also impact and overlap with how we think about high
performance in startups, so in the next chapter we’ll continue that flow
into the world of performance.
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Summary
1. Being part of a high-growth startup is a reason to
invest in and focus on learning, not an excuse to do
the opposite. I typically start with the growth and
development culture and nurturing that, nailing
onboarding and building a great team of managers
to amplify impact across teams.
2. It can be easy to think of learning as a series of

online courses, conferences, or reading books.
But that’s not where most of the learning actually
comes from. Our approach to learning needs to be
grounded in experiences for people – tackling new
projects, mentorships, learning from mistakes, and
stretching responsibilities.
3. Progression doesn’t have to mean promotion, and

it will mean something different for everyone. For
our work in this space to be effective, we need
to understand and tailor our work to how each
individual views their own progression and what
they’re trying to work toward.
4. Peer feedback is equally as helpful as it is dangerous.

We should carefully plan how we build skills in
giving meaningful feedback, ensure appropriate and
safe forums in which that feedback is provided, and
help our people know what to do with feedback too.
5. Not all resignations are bad. There are great reasons

to leave a business, and when someone leaves who
has aspirations to do things simply not possible in
our business, we should be excited for them and
grateful for their time with us.
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CHAPTER 8
Performance
In the last chapter we explored how we learn in the context of startups, and
some of the mental notes I’ve taken to approach this very broad area. One
of the themes through learning is the growth of our people. In a startup
environment, growth is critical to how we also think about performance –
the mindset and behaviors required by managers to support their team
members, the clarity of direction and goals that ensure everyone is pointed
in the right direction, and how we think about the cycle of performance
and development in the context of a rapidly growing and scaling startup.
This chapter continues that chain of development and growth from
Learning and shares the lessons and principles that have stuck with me
when thinking about high performance and how we create environments
where our team members can thrive.
The Trinity: What, How, Where?

Typically, when we think about performance and how we help both
managers and their team members, we spend an awful amount of time
talking about goals and underperformance. Goals can be super powerful
and create alignment and buy-in, which is necessary and gets increasingly
harder as the business grows and becomes more complex. And
underperformance is an unfortunate reality of managing people. Even the
best teams have an underperformance quotient that they need to manage.

Chapter 8 Performance
This emphasis on goals and underperformance, as important as they

both may be, both relate to specific steps in performance rather than how
we actually go about driving performance. Managers have a tough gig
in this regard. A lot of the training they have done in the past introduces
an abundance of theories, models, frameworks, and concepts for how
to manage performance, and people, well. It’s a monumental amount
of information to take in and it’s easy to feel overwhelmed. And let’s
not forget what was shared in the previous chapter around how people
learn too!
I’d guess two or three times a week, I speak with a manager or team
member about something performance-related within their team.
Something mightn’t be clicking between the manager and team member,
or there’s ambiguity around the role or expectations, or something
personal going on, or one or either of them have no idea what the point of
the work even is. It’s a surprisingly finite list of things that tend to get in the
way of the peak performance we’re trying to find.
It’s especially hard for managers who are managing a team for the first
time. Being able to take all of the things, and all of the advice, for what they
know they should be doing and convert it into action that is effective. As
I reflected on hundreds of these conversations with managers and team
members, I was trying to find a silver bullet for how we prevent this from
happening. It doesn’t exist. But there are patterns with the sort of things
that regardless of team, experience, and personality continue to pop
up. Boiled down to their simplest form, they’ve become a series of three
questions.
This is a model (I know, another model to add to the mix) I’ve been
using for a number of years with managers and team members alike. I
frame it as making sure the 101s are in place and constantly revisited and
reinforced throughout the interactions that happen between managers
and their team members. Secretly, it’s been more about trying to
proactively reduce the likelihood of people and performance problems
ending up with the People team to help work through.
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The model is this: as a manager, if you do nothing else, make sure you
help your people answer these three questions:
1. What am I doing?
2. How am I going?
3. Where am I going?
Let’s break it down a bit further. “What am I doing?” is about role

clarity and expectations. While some team members might intuitively
know what they need to be delivering, for the vast majority we need
to revisit this all the time and be explicit about what we’re working on.
This means prioritizing what comes first to avoid a misfire of focus, clear
expectations for what is delivered and, by when, any barriers or roadblocks
that might put this at risk, and generally having an open discussion with
each team member to understand their workload and where they are
spending their time. Quick reminder: This doesn’t require a thrice-daily
Slack message to check in on what someone is doing. You can cover all of
this as part of your 1-1 and should carve space out for exactly this.
“How am I going?” is a bit of a double-edged question, so it could easily
be split into two components. Firstly, it’s a check in for how your team
member is going. What’s on their mind, how they’re feeling about their
work, and assuming you know them well enough and they’re comfortable
with this, how things are going outside of work too. Usually we kick off a 1-1
with a question that touches on this, before accepting the default “pretty
good” response and moving straight to the next thing. This question is really
about making sure you’re in tune with your team members. The second
component is helping your team members understand how they are going
in their role or with the work they’re doing. Humans need reinforcement,
encouragement, praise, and sometimes correction and alignment. And in a
work setting, the feedback provided by managers for any of those purposes
is gold dust. Never assume your team member knows how you’re feeling
about their performance. And please, never operate the “no feedback is
good feedback” management style. Your team deserves better than that.
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“Where am I going?” relates to purpose and direction for both the

business and each team member. As startups grow, the mission can feel
quickly removed from the day to day and it’s vital to performance and
motivation that people see the link between what they’re working on, what
others are working on, and overall what the business is trying to achieve.
This also aids in building empathy and a team mentality for when things
go awry or not to plan (these are called weekdays in startups, so doubly
important!). Direction can also be at a very individual level and relates to
how we perceive growth and progress from the last chapter. The day-to-
day roller coaster of work can sometimes cause tunnel vision and it can be
difficult to see what we might be working toward from a personal level.
These three questions don’t only apply to managers but also to team
members too, with a slight reframe. When we’re feeling like things aren’t
quite clicking the best they could be with our managers, or there’s been
some misalignment or conflict, these are three questions that can help
bring back the clarity, purpose, and alignment needed to operate more
smoothly.
I Messed Up OKRs, Twice!

I’m about as far from an OKR expert as you can be, especially for someone
in my role. I dove head first into OKRs on two occasions and would kill
to have my time again. As is the theme with almost everything in this
book though, messing up is rarely a bad thing and it’s given me some
much needed perspective on why I should never underestimate OKRs or
generally how we go about setting and communicating goals.
For the record, this lesson is not about criticizing OKRs, but rather the
reality check from implementing them poorly.
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The first time we launched OKRs, our aim was to bring the whole
company on board with a bottom-up build of initiatives that would
feed our top-level objectives. We hosted workshops, facilitated team
discussions, and gave everyone the opportunity to contribute to how we
were going to smash it out of the park that quarter. Even with a relatively
small team we had hundreds of initiatives contributed. Some of them
related to the company objectives and many others fell into the “these
would be good to do at some point” bucket. The prioritization of these
left a lot to be desired, but we ended up with a set of initiatives and some
half-baked key results and metrics. Good enough, we thought, and we set
sail into the quarter! What became brutally obvious as we moved through
the quarter is that we’d gone through the entire process seemingly blind to
the day-to-day of the startup. Almost every single initiative was something
new to improve or enable the business. There’s plenty of value in that, but
we were going into OKR progress updates and hearing feedback like not
having enough time to meaningfully move forward most of the initiatives.
We’d placed OKRs on top of everything in the business, rather than
integrated into what we were doing, and it ended up only having a slither
of the positive impact it was capable of having.
The second time around was painfully amusing (in hindsight, it was
less amusing at the time!). We overcorrected and then some! We found a
better balance of objectives and key results that reflected both incremental
growth to our core business and some opportunities and threats that we
carved out as focus areas. It wasn’t until one of the final OKR progress
updates that we sat around chuckling at the fact our sales team had hit
almost all of their key results without completing a single initiative. On
one hand, we can’t complain too much as hitting the key results is a great
outcome for the business. On the other hand, we still failed to bring value
from the methodology and couldn’t be confident of the link we’d created
from initiatives to key results to objectives.
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During future goal-setting processes at this startup and others, I’ve

probably been a bit adverse to most of the methodologies that exist and it’s
only been more recently I’ve come back to believe in the power of the link
between the work that we do individually to the measurable outcomes for
the business that contribute to our objectives. Something that I reflect on
often with my brief foray into OKRs is the need to contextualize according
to the stage of the business. We do this in almost every other part of the
people landscape, from how we approach recruitment and onboarding
to how we do compensation and benefits. I skipped this step with OKRs
and tried to achieve a methodology rather than using and adjusting a
methodology to achieve the business goal.
The value of OKRs wasn’t void during this process. It was messy and
ineffective in a lot of places, and we probably wasted too much time
working out whether we were aiming for three or four of a certain outcome
as part of defining key results. But what it did do is put front and center a
cadence to come back and communicate more about our objectives and
what we were trying to achieve. Every month we were talking about the
same thing, and then during the month it came up again and again in team
meetings. Our team became fluent in our direction and ambition, even if
we muddled everything below this. And that’s a pretty good outcome as a
starting point to build on again.
eople Outgrow Startups; Startups

P
Outgrow People
During an interview process for a new role, the Founder and CEO and I
were discussing some of the pains of growing the size of the team by a large
multiple year on year. Toward the end of this, he asked me, “What’s one
piece of advice you wish you were given before your last growth journey?.”
And I said this: “People will outgrow you, and you will outgrow people. Both
of those things are fine.”
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In the previous chapter, I shared the concept of people and startups

outgrowing each other as part of the focus on growth culture. It crosses
over both performance and learning, and it’s arguably a lesson from my
time in all startups that never stops resonating. Or being true. Startups are
incredibly fluid businesses. They experience significant amounts of change
in a short space of time, which is why there’s an adage within startups that
a year in a startup is worth two anywhere else. We’ve become accustomed
to hyper-growth stories, where a small team with early traction and some
investment quickly balloons to having a huge valuation, several hundred
or even thousands of people, and sometimes still expanding. These
startups needed to continuously reinvent itself, and it’s likely that every
couple of years the business would have felt unrecognizable by some.
I covered the perfect resignation at the end of the previous chapter
which is the best reason why someone might outgrow a startup. But it’s
probably not the most common, which is the scenario where a team
member is seeking a step up to a role that doesn’t exist at that startup,
either because it’s occupied or because it doesn’t exist yet, and they go
and pursue that elsewhere. The growth curve of many team members can
be just as steep as the growth curve of the startup, and I’ve come to accept
the reality that there’s always going to be a subset of this scenario that
you can’t plan for or fix, and that the best thing for that team member as a
person might well be in another business.
The second part to this lesson is the reverse, which is an unfortunate
reality of growing quickly especially in senior roles. Let’s take a B2B
education technology startup which is experiencing significant revenue,
customer, and team growth. Within their first few years, they might have
grown their revenue from $1 million to $10 million, and in the few years
after that, from $10 million to $50 million. Their customer numbers have
gone from tens to thousands, and their 15-person team as part of an
early stage of funding is now several hundred. While this all will happen
within one startup, for those part of that journey it will have felt like they
experienced several startups. The journey to the first $1 million in revenue
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is scrappy and all about initial traction, feedback, and market fit. To $10
million, it shifts to go-to-market, technology development, and stability,
and reaching that period where scaling a business is possible. And to $50
million, it becomes about the ability to grow in a repeatable and scalable
way. Each of these environments looks vastly different, and while some
people can thrive across different stages of growth, most people generally
have a stage of growth that is their jam.
Imagine you’re hiring your first sales leadership role. You have a
couple of million in revenue and some sales reps in place. You’re now
looking for a sales leader to take the early stages of the playbook and likely
take over sales leadership from a Founder. They might be expected to be a
player-coach, securing revenue through new deals but also building
foundations for a revenue engine capable of doubling or tripling revenue.
If you were hiring for this role, you’re unlikely to want to hire the sales
leader who has spent their career in $100 million revenue organizations
with all of the infrastructure in place already. You’ll be looking for
someone you have confidence in to deliver what you need in your startup
at your stage of growth. And if all things go well in the coming years, that
sales leadership roles start to look very different. Almost unrecognizable
from the role you needed not long ago. It’s possible your sales leader can
grow with the role, or might have had experience across multiple stages
of growth and can bring transferable learnings, but if they’re like many
leaders in the startup space who have built their success on that stage of
growth only, you may well outgrow them and need to bring in a different
sales leadership role.
This same scenario can apply to almost every part of a startup. My
jam is pretty early in startups, typically as the first People or HR hire. If a
scale-up already has 1,000 people across 20 countries and with a 30-person
People team, they’re likely to need a leader who brings their experience
and learning from that stage of growth. Equally, that leader would have
likely found the experience of being the first People hire to be quite the
shock if they haven’t done it before… Just like I did.
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I’m a big believer and advocate of finding paths for as many people
as possible to grow with our startup, but not blind to the fact that with a
business that experiences such significant change and transformation
in a short space of time, it’s OK to outgrow someone. Just like it’s OK for
someone to outgrow us.
P.S. One day, I will tackle the 1,000-person scale-up!
If I Hear “Hire Slow, Fire Fast” One

More Time…
It’s the business adage gift that just keeps on giving. Take your time hiring
and be highly selective and sure of the people you bring in. And if they’re
not working out, remove them quickly. I won’t argue with what you might
think are the opposite practices to this. Any startup that hires whoever
they can find in order to grow quickly and then allows for continued
underperformance or a strong values misfit is probably going to hit choppy
waters really fast and require a lot of reparation.
But let’s not kid ourselves into thinking that “hire slow, fire fast” is the
goalposts for startups, or any business for that matter. For years, we’ve
built recruitment processes made up of six, eight, or even ten stages to put
candidates through every possible test, most of which are pointless, to try
and perfect the science of hiring perfectly. Most major tech brands are all
renowned for convoluted assessments and needing to spend significant
amounts of unpaid time and expertise trying to give them an extra 0.1%
confidence in the hire. They can do this because their brand and offering
is so attractive to so many people that candidates will try and fight through
the process, in hope that greener pastures are on the other side.
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I’ve experienced a recruitment process that dragged on for months and

had six stages before I withdrew. My engagement with the process went
something like this:
–– Stage 1: Consider me interested.
–– Stage 2: I like this a lot. Very interested!
–– Stage 3: Hire me please!
–– Stage 4: OK, fine, but get to the point.
–– Stage 5: Sigh, really?
–– Stage 6: I’m not interested.
Now I may not have been that 10/10 hire for them, but I have to trust
that at Stage 6, there must be enough interest at their end to want to keep
investing their time, and to keep trying to test one more thing. By the end
of this process, it didn’t matter how strong of a fit I was because I had lost
my interest and engagement in the process.
I suggest a change to the first part of this adage. Don’t hire slow.
Hire with purpose. Design a process to test the critical requirements and
components of the role that allows for decision-makers to arrive at a
conclusion in the quickest amount of time. If you’re taking over a month
to hire someone, with the exception of processes that involve a lot of travel
or logistical challenges, it means you’re not sure what you’re looking for
or how to know you’ve found it. Invest time early in the process, before
candidates are engaged, to make sure your hiring process is purposeful,
but not slow.
Fire fast. There are circumstances where this is simply bang on. Where
behaviors and values in particular are compromised, the effect of allowing
this to continue is infectious and toxic. Similarly, if someone new is not
working out, or where a performance issue continues to not improve after
you’ve made genuine attempts to try and solve this, taking action quickly
makes a lot of sense.
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However, once again I can’t help but notice that the preceding
examples are usually not the scenarios where fire fast is used as a tactic.
The countless examples of people unexpectedly losing their job after
providing feedback on something or someone in the business, the
performance issues that go unmanaged for months and sometimes years
before a quick process is run to exit someone, and let’s not forget the
layoffs that plague the tech industry and the obsession when an indicator
turns red to reduce the team size (the same people put through months
of recruitment stages to make sure they’re just right for that culture and
role). That’s how fire fast plays out in too many startups and it does the
ecosystem and People teams no favors by this behavior continuing to exist.
So it feels appropriate for a change to the second half of this adage.
Don’t just fire fast. Fire thoughtfully. Fire as though it was you receiving
the news, or a member of your family. Exhaust every reasonable avenue to
resolve situations before needing to make the call to part ways. And if that
doesn’t work, fire respectfully and with sensitivity. These decisions affect
people for years and can easily come back to bite your brand for both
employees and customers.
The Death of Performance Reviews?

My first experience of a performance review was in a 50,000-person
company. It was exactly as you expected. An annual review, a performance
rating from 1–5, and a salary and bonus outcome determined by this.
I always thought it seemed a really sensible approach to linking in
performance and reward, and I still do. The piece I was missing though
which I didn’t realize at the time is how fortunate I was to have a series
of managers who were all very strong at what they did, and it was their
leadership behaviors that enabled that system to work.
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The longer I spent in HR and People teams, the more it felt like my
experience of performance reviews was an anomaly. I would hear of people
who felt like they had nailed it in their roles to be told they are “meeting
expectations.” Or they were told by their managers that they would rate
them higher but they’re only allowed a certain number of people above
a line. Or a whole year’s worth of feedback was collated and dumped in
one go on the team member, and told where to improve for next year. It
shouldn’t be surprising that we look at the system and think “it needs to go.”
As more and more businesses started sharing their plans to remove
the annual performance review and move to continuous feedback or other
cycles, I felt like I had to get in on it. Every major consultancy in the world
was publishing reports on the death of performance reviews, so surely
there had to be some merit behind this, right? Fast forward to today and
I’ve had the opportunity to design and implement a few different types of
performance cycles, and also spend time with a lot of other people doing
the same in their businesses. I found great amusement in two scenarios
that I kept hearing. Neither of them are bad scenarios. Just amusing ones.
1. We’ve replaced annual performance reviews

with quarterly performance check-ins, and we’ve
decoupled performance and reward outcomes.
Salaries are now set based on the market with
high performers being incentivized through other
compensation means. It’s a shiny way of saying
we’re designing for more frequent feedback and
still linking performance and reward but in a less
clear way.
2. We’ve removed performance ratings and instead use

a framework or matrix to calibrate reward outcomes
to make sure they’re consistent. This is also known
as using a form of performance rating, but without
the team members knowing.
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I am being flippant with these scenarios to highlight a couple of things

that can be lost in performance cycle decisions. Firstly, we need to view
our performance cycles from a team member’s perspective first. At its core
I believe we’re all looking for similar things within a performance system –
recognition for the work we do, feedback on how we’re going and how we
can grow, a feeling that we and our team mates are being treated fairly, and
confidence that we’ll be financially rewarded for performing well. If we
know these to be true for most people, it stands to reason that almost every
performance system could work. This leads to a second point, and perhaps
the summary of what I have had to learn. The culture and leadership
behaviors of a business determine the effectiveness of a performance
system. It’s not the system itself that fails a business, but rather how well
it’s implemented and supported.
Given every startup will have a different culture, I don’t believe in a
single, correct performance system that will be effective by design. Instead,
I wanted to share a number of areas to consider to help enable whatever
performance system you decide on.
Forced Distribution
Possibly the most famous gripe of an annual performance rating. Also
known as a bell curve, this is where it is assumed every team will, and
therefore must have, a distribution of performance ratings. The origin
of this isn’t grounded in some theory of human behavior, as common
as it may be to see some sort of distribution. It’s instead grounded in
budget. Where a link between performance and reward exists, there
is a budget line item to cover salary increases, bonuses, and any other
form of compensation. This is typically done on a “middle of the curve”
basis, so if you budget a 3% salary increase across the board, your middle
performance rating will receive something around that level, and in order
to fund your high performers receiving more than that, you need an
equivalent set of low performers to receive less than 3% and balance it out.
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Budgeting for performance-based reward is always tricky, especially

in high-growth companies where typically your ability to fund reward
outcomes comes from meeting revenue expectations which can be steep
targets. A different way to think about this is to budget higher than “middle
of the curve.” The idea you’re budgeting for a 2–3% increase to cover cost
of living and expecting high performance from your team members makes
no sense. If you’re striving to embed a high-performing culture and tackle
steep ambitions, you should be budgeting for the high performance your
team will need to display to reach that. If the results validate this at the end
of the year, you have budget to financially recognize your team.
If you’re using ratings, the biggest concern your people will have is forced
distribution, so you need to make sure this doesn’t sneak into the process
and provide enough clarity and transparency on the link between ratings and
reward to allay concerns that they’ll be rated based on how they stack up to
the rest of the team rather than on their own individual performance merits.
Review Bias
This is largely a manager capability and one of the most important roles
a People team can play. There are so many natural, human biases that
impact our perception of our own and other people’s performance. Being
aware of things like recency, attribution, and halo/horns in advance,
setting clear expectations and calibration between managers in advance
of feedback and review conversations, and having a feedback loop on
the process itself from both managers and team members can all help to
identify and mitigate the impact of biases playing out.
Deferred Feedback
Ah yes, the old “hold that until their review” which might be in four weeks
or eight months depending on how deferred the feedback really is. One of
the best parts of the rethinking of performance reviews across companies
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has been the recognition of deferred feedback. The value of feedback that
is held until a performance review is a fraction of what is can be if delivered
in a timely and continuous way.
The test I use with managers where a periodic performance review
process happens is this – there should not be anything new raised in this
conversation. The performance review is a reflection, not an opportunity
to bring up new feedback. That should have taken place already, and if not,
it’s a reflection on the manager’s performance, not the team member.
Rating Emphasis
There’s some nuance to ratings and a few challenges with how they’re
implemented. One of the main ones I have stumbled on a few times
is where the rating itself, especially the title of a rating, gets in the way
of a meaningful conversation. This is a risk of the direct link between
performance and reward and often why I try to keep the rating as part of
a reward conversation rather than as part of a performance conversation.
As humans, we see the number 3 on a 5-point scale as meaning average,
even if you intend it otherwise. Similarly, “meeting expectations” can feel
really underwhelming if the feedback you receive is that you’ve gone over
and above.
Performance ratings aren’t for every business, so it’s a judgment call on
what will be effective within your culture. If you do use them, engage your
team members early in the design of these and listen to their feedback and
suggestions on how they are applied.
This chapter was the last of four chapters dedicated to key functional
and lifecycle areas within our People experience: Recruitment, Reward,
Learning, and Performance. In the next chapter, I wanted to call out
something very specific which has become much more topical and
relevant since 2020. You guessed it, remote working.
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Summary
1. Managing a team can feel overwhelming trying
to get everything right and avoid all of the pitfalls
you’ve been warned about. It can be helpful to strip
it back to fundamentals. If you do nothing else for
the moment, make sure you help each person in
your team answer these three questions: What am I
doing? How am I going? Where am I going?
2. If you’re building a goal-setting process for the first

time, don’t be afraid to experiment and don’t be
disheartened if you get it wrong. I messed it up a few
times, and with each iteration and improvement, it
gets closer to a great goal-setting process.
3. There are two truths about people and startups.

Number one: people outgrow startups. Number
two: startups outgrow people. Both are perfectly OK
when we can’t find a path for someone.
4. Swap out your “hire slow, fire fast” mentality for

one that is people-first. Hire with purpose. Design
a process to test the critical requirements and
components of the role that allows for decision-
makers to arrive at a conclusion in the quickest
amount of time. Fire thoughtfully, as though it was
you or a member of your family receiving the news.
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5. It can be difficult to know what best practice

performance reviews look like, but in my experience
it’s the culture of the business and the manager’s
behaviors that have the most impact on success
rather than the specific design of the performance
cycle. Avoid forced distribution and deferred
feedback, identify and mitigate reviewer bias, and
be mindful of how you define ratings if you choose
to use them.
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CHAPTER 9
Remote Working
While there are fascinating links between remote working and the
components of our People experience that we’ve covered in the last
four chapters, it feels necessary to call out this topic specifically given its
relevance since the Covid-19 pandemic. This chapter shares some pointed
observations about how we’ve coped with and continue to manage remote
working, as well as how we start to think about flexibility and the rise of the
remote manager.
The Covid-19 Acceleration

Remote working existed long before the Covid-19 pandemic. Some truly
incredible businesses built remote teams and cultures that have been
enviable examples for others. And in the space of a few weeks, the vast
majority of white-collar work was forced into our homes, bedrooms, living
rooms, and families as restrictions set in across the globe. For these people
and businesses, remote work was now the status quo.
Remote work is not any better or worse overall than non-remote work.
For some people and startups, it works well. For others, it doesn’t. And
that’s perfectly OK. There can be more than one correct answer and the
constant battle between remote work advocates and critics alike is pretty
pointless.

Chapter 9 Remote Working
The pandemic represented a fascinating change curve for a lot of

businesses. There wasn’t time for planning. Most businesses probably
treated it as a continuity crisis. In addition to widespread illness, wellbeing
concerns, trauma, and loss, remote work was forced into many workplaces
and we needed to make lemonade. And so that is what happened.
Businesses with decades of in-office history made swift and impactful
changes to allow for continuity. It didn’t matter if you were a remote work
advocate or not, you simply had to make do.
Very few good things can ever come out of an event like a pandemic.
But we witnessed a symptom of the pandemic which was the adoption and
practices of remote work. We experienced possibly decades of progress
with remote work adoption in the space of twelve months, and so now as
we come out of the pandemic, we shouldn’t be surprised to remain in a
teething period for quite some time. The change was a shock to the system,
and now that a choice has returned for a lot of businesses, we’re starting to
cast a more critical eye on the sort of arrangement and culture we’re trying
to build.
emote Work Is Uncovering Our

R
Dirty Laundry
“How will I know they’re working and not slacking off?”
“You can’t be as productive from home as you can be in an
office. There are too many distractions at home.”
“We value flexibility and you’re allowed to work remotely one
day per week.”
My word we are airing some dirty laundry, aren’t we? Whether you’re
a fan of remote working or not, I’d like to think the acceleration of progress
in remote working, especially how to do remote working well, is a great
thing. It’s opened up a much broader understanding of how we behave
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and think as humans, and how we operate as part of a team and business.
It’s also brought out our dirty laundry. They aren’t secrets in the world
of work, but rather have been amplified through the transition to remote
working and have taken center stage as businesses consider the work
arrangements of their teams.
Performance
There is no better way to say you don’t know how to measure the
performance of your team than to be genuinely concerned they are
slacking off when they’re at home. Because if you did know how to
measure a team member’s performance, you wouldn’t be concerned. At
worst, you’d be really curious. It might take a moment of self-reflection for
each manager, myself included because I too have been guilty of this, to
question if the physical presence of someone working near you in an office
has been mistaken for performance, even on a very small scale.
When we identify and remove that mistake, it allows us to start over
with how we think about performance for each team member. Working
together to define outcomes and goals rather than just inputs and effort.
And once those are defined, let’s be curious about how or if remote
working influences that.
Trust
Trust is central to the relationship between managers and their team
members, and remote working has added some chaos to that trust. There
is a logical follow-on from the example earlier about worrying that a team
member is slacking off. A big part of that is performance, and another
part is likely trust. Highly trusting relationships would already have the
empathy and authenticity behind it to work through that belief system and
arrive at a positive outcome.
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Trust played out in the world of remote working in a whole variety

of ways. Take those people who joined remote companies during or just
after the pandemic. They joined under an agreement that they would be
in a remote role, and once offices started reopening, many were met with
requirements to relocate to be in an office for a period of time, or risk
losing their jobs. The same thing applies to the sheer volume of layoffs
that took place in the last few years, sometimes leaving people without key
benefits or any level of financial stability until their next role. If we want
to talk about how to erode trust in the shortest number of steps, there is
basically a playbook on our door from the last couple of years.
Trust is complex and dynamic and takes a long time to build and
nurture. Remote working has aired the poor state of trust between many
managers and their team members, and between team members, and is
now contributing to some of the blanket decisions being made to enforce
working arrangements in a certain way. It should come as no surprise that
so many of the fully remote businesses who operated that way since well
before the pandemic cite building trust and relationships as so core to
their values and ways of working.
Culture
There’s been a meme floating around since offices started reopening at
the back end of the pandemic. It shows a lifeless office of cubicles with
words to the effect of “we’re returning to the office because we care about
our culture.” If you remember back to Chapter 3, you’ll already know my
opinion about culture relating to something so insignificant like an office.
But this meme didn’t become so popular just because it was funny.
For so many people, this was real. Their business had chosen to return
to the office under the banner of trying to nurture their culture, without
any real shared understanding of what that even means. There may well
be some very valid parts to how they’re thinking about their culture in
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a deliberate way, but without this context or any detail around what
specifically they are trying to achieve, it will continue to be perceived in its
most negative light (and rightly so).
Culture happens whether we like it or not. And as we already discussed
in Chapter 3, the question is around how deliberate and purposeful we
want to be with the culture we’re building. There are great cultures within
remote companies and great cultures within non-remote companies,
just like there are poor cultures within both too. We should start with the
culture we’re trying to build to understand the role of remote, hybrid, and
in-person arrangements in helping to shape and reinforce that culture.
now the Difference Between Flexible

K
and Remote Work
At risk of sounding a wee bit condescending, I thought it might be
helpful to recount the definitions of a few terms we continue to use more
interchangeably than we should.
Remote. Hybrid. Flexible.
It can be easy to blur the lines between these when describing the sort
of arrangements that take place or might be possible. Similarly, we might
describe how we prefer to work individually in a different way to others or
different to how businesses describe their setup.
Remote
This describes working outside of a company’s office or place of business.
It doesn’t have to mean working from home. It might mean working from
a bookstore or working from my parents’ house in Australia. Sometimes,
businesses will define it one layer further with additional terms below
which I’ll share the going understanding of:
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–– Fully remote: Everyone works remotely all the time.

Some companies will give complete choice around
where their team chooses to work also.
–– Remote-first: Everyone is assumed to be working

remotely but there could still be options to work from
an office location. Typically, these businesses will
structure their operations around a remote team.
–– Remote-friendly: Everyone is allowed to work remotely

at least some of the time, but they aren’t assumed to be
doing so. This is sometimes known as a combination of
hybrid and remote, as some people will use an office
and some people may be fully remote.
Hybrid
Hybrid assumes that everyone needs to be in a company’s office or place
of business at least part of the time. Businesses that require a day per week,
or a week per month, for instance, would be described as hybrid. Hybrid
assumes there will be times when everyone is together and when everyone
is apart.
Flexible
Flexible work cuts across remote, hybrid, and in-person work
arrangements, but it can be difficult to separate out the language given
how readily remote and hybrid work are described as flexible work.
Flexibility is where work can be adjusted by a team member based on
their needs. It might be where work is done, or how it’s done, or when it’s
done. Flexibility can exist in all forms of remote, hybrid, and in-person
arrangements and can also be missing from all of them too. A company
that mandates every team member must work from home and with set
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hours and breaks is not somewhere a lot of people would describe as being
flexible, even if it’s remote. Similarly, it can be tempting to describe hybrid
arrangements that require two days a week in an office as being inflexible.
For some, they might consider that. But if you have the ability to set those
two days, to increase or decrease it as other things arise, and to also adjust
hours and breaks to what works for you, you might find there are a lot of
options for flexibility.
The reason why defining these individually is important is to uncouple
flexibility from the concept of remote, hybrid, and in-person working.
By simply choosing an arrangement, we’re not automatically flexible or
inflexible, and we still need to be in sync with the sort of flexibility that our
team members might be looking for in order for a work arrangement to
work for them.
The Remote Manager

I’ve worked in a number of different remote businesses and been fortunate
enough to work with some exceptional managers who have taught me
a lot about how remoteness can influence how we engage, motivate,
and interact with our teams. I genuinely feel for all of the managers who
became overnight remote managers during the pandemic. As humans, we
all had things to deal with in our lives, and managers had an extra pressure
on their ability to transition to remote management and wear that hat well
for their team.
There are a lot of tweaks to management style and behaviors that
remoteness requires, but overwhelmingly I’ve found there are consistently
three areas of remote management where the exceptional managers stand
tall. They nail these three things, and as remote working continues to
become more prevalent and understood in the coming years, I fully expect
these will start to appear more explicitly on.
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Synchronous and Asynchronous Communication

There’s a fine art to communicating with remote team members and
knowing what sort of communication will achieve the best outcome for
each team member. Unsurprisingly, things like 1-1s and social activities
are almost always synchronous and fundamentally designed to bring
people together. Likewise, purposeful synchronous forums to allow for
discussion and debate, coupled with asynchronous forums where time
zones impact participation, make sure that each person still feels included
regardless of where they are at. And, something that is consistently
underrated, a culture of writing and documentation to record discussions
and decisions, clarify processes and steps, and help support the self-
service of new team members.
Onboarding
Speaking of new team members, onboarding remotely has a different
flavor to rocking up to an office for your first day. But for these exceptional
managers, onboarding never started on day one. It started way back in
the recruitment process with the expectations and transparency they
demonstrated around how their teams worked and even some of the
challenges. And once someone had accepted an offer, preboarding
processes were in place to start to prepare someone for stepping into the
team, especially making sure they knew what their onboarding would look
like, what equipment and support they’d have, and how they’d meet and
work with their new teammates.
In Tune with Work and Well-being

I remember being in an interview for a developer who would be joining a
fully remote team. When we were talking about remoteness and how they
liked to work within remote teams, they made a comment around how
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they appreciated managers who knew and trusted what they were doing
but didn’t feel the need to check in on Slack ten times a day to make sure
of it. It stuck with me, for both the honesty and for a nuance in remote
management that exceptional managers just seem to nail. Being in tune
with each team member’s work and their well-being.
There’s a balance to staying in tune without coming across
overbearing, especially when you lose some of the body language from in-
person conversations. Exceptional managers carve our time to deliberately
and purposefully discuss work and work outcomes (and trusting it gets
done when they say it’ll be done) and also on how people are going as
humans. Meaningful check-ins to learn about them as individuals and
explore how they’re thinking and feeling about things.
Burnout Is Our New Thanos

It’s a logical flow from the previous lesson around being in tune with each
team member’s well-being, and especially important given some truly
sobering statistics that are coming to light around how burnout, stress, and
pressure play out on remote team members.
Over 35% of men and 42% of women feeling consistently burnt out at
work was reported by McKinsey. Some other publications reveal this rate
to be much higher too. Zippia found that two-thirds of remote workers feel
pressured to be available all the time. And it’s been shown consistently in
research for years that those who experience burnout are more likely to be
absent. Gallup’s research puts this into perspective – team members who
feel burnt out are 63% more likely to call in sick, and 2.6 times more likely
to be looking for a new job.
Now, before we assume that remote work is the cause, the statistics
for hybrid and in-office teams are not that much better. It turns out,
burnout is increasingly a risk for everyone. But remote work puts a unique
strain on team members through the blur between their work and their
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nonwork lives. A lot of us will have seen how easily it can play out during
the pandemic, including me. Your desk and your bed may only be feet
apart, and with most of our tools available on our phone too, it seems
inconsequential at 7 a.m. with breakfast or at 8 p.m. when watching
television with the family to fire away a few emails or send a Slack or Teams
message back to the boss. This risk exists for non-remote workers too, but
there’s a more clearly defined work day which helps some people transition
from work to the rest of their life. That delineation is less clear for remote
team members who need to mentally check in and check out of work to
force it, even when their systems and tools are always close to hand.
The next chapter is the last chapter, but we take a sharp right turn to
talk about something much more individual than our collective People
experience: your career.
Summary
1. The Covid-19 pandemic accelerated decades of
progress with remote work adoption in the space
of 12 months. Now that we’ve come out of the
pandemic and greater choice exists, we should
expect to be in a teething period for quite some time
as we learn more about how various arrangements
can contribute to our teams and culture.
2. Remote work has broadened our understanding

of how we think about human behavior and
performance in different contexts. It also aired our
dirty laundry, in particular whether we actually know
how to measure performance, how we perceive and
build trust in relationships, and the (lack of) depth in
our understanding of culture and what drives it.
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3. Be precise in how you describe work arrangements.

Remote work and flexible work are two different
things, and we should uncouple our thinking on
these as being related.
4. A new role has been introduced through the

pandemic in many companies – the remote
manager. There are three areas, in my experience,
where remote managers consistently excel –
blending synchronous and asynchronous
communication, onboarding, and staying in tune
with both work and well-being.
5. While burnout is prevalent and increasing across all

work arrangements, remote work has added a new
lens to how we identify and respond to unique risks
of burnout that it poses, in particular around the
blurring between our work and nonwork lives.
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CHAPTER 10
Your Career
This chapter has a bit of a different feel to it. I want to talk about myself.
And you. And every member of a HR or People team too. Every lesson
in this chapter is something I have struggled with throughout my career.
Some of them I still do and need to remind myself constantly to maintain
perspective.
There is a People team flavor to most of what I share in this chapter, but
many of the things I struggle with I know others do too, in different parts of
the business and in different stages of their career. So I like to think there’s
something here for everyone.
now the Difference Between Who You Are

K
and What You Do
I’ve worked with mentors and coaches at various points throughout my
career and a topic that has come up a number of times relates to my
identity, both personally and professionally. Not only how I see myself,
but also how I think others see me, and how I want them to see me.
Throughout these conversations, there’s a question that really stuck with
me and it fits firmly into the bucket I described of things I need to remind
myself constantly.
If you lose your job, who are you?

Chapter 10 Your Career
It’s not intended to be a deep philosophical question even though it

sounds a bit that way. It’s simply a guide for reflection. The very delicate
balance that I’m sure many of us all live each day is that of who we are
and what we do. It can be hard to differentiate these sometimes. When
I’m in my zone and passionate about what I’m doing, sometimes my
entire view of myself becomes my job title. And it’s easy enough to do. We
spend our working hours, days, and weeks playing a part in companies,
and regardless of what part we play, it feels very human that we start to
see ourselves as that part. We introduce ourselves to new people and go
straight to what we do for work.
So if that work no longer exists, by your choice or someone else’s, who
are you? What gives you passion? How would you introduce yourself to
someone you met at an event? Are you a parent? A cyclist? Do you volunteer
at a local shelter? Are you part of a community or sports group? These are the
things that can and should fill our identity buckets. So if we lose one of them,
we’re only pouring out a splash and replacing it. Not the whole bucket.
Having breadth in my identity has been a focus for a number of years
now. Having been through a redundancy process and feeling it necessary
to quit a different job immediately, I’m slowly getting comfortable with the
fact that as much as I might enjoy my work on the whole, it is always less
permanent than I give it credit for. Change is inevitable, so if I do need to
part ways with my job for whatever reason, there are enough other parts
to my identity and passion that mean I can wake up the next morning still
feeling a sense of energy, purpose, and direction.
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e Clear on What Your Role Is and What

B
It Isn’t
Depending on your experience and exposure, the role of a HR or People
professional can have a very different meaning to the person sitting next to
you. And different again from the next person. There are operational support
roles, “back office,” business partners, strategic advisory roles, “people
people” roles, and of course the “HR but you’re mostly a recruiter” roles.
When you’re the first People hire in a startup, there’s a bit more
freedom to define how the role and function shapes up. There are also
existing expectations about the role too, so, just like the myth of a blank
canvas we covered in Chapter 1, you’re unlikely to be building from
scratch. In the first startup I joined, the CEO described a cathartic response
from people. I became a sponge for all of the good and bad, which is fine
at first to get under the skin of how things happen. But once you multiply
your team size that needs adjusting, and the intent of my role was to build
a people function, not just be a therapist.
The principle that came out of this was defining the people function as
not existing to solve problems, but to help others solve their own problems
and prevent the number of problems in the first place. How that played out
was in approaching conversations using coaching techniques, allowing
others to experiment, fail, and learn, and making sure our People team
processes were constantly looking at how to arm team members and
managers to be informed, empowered, and accountable. Hiring managers
were accountable for the hiring in the teams, supported by our Talent
Acquisition team as a “guide by the side.” Similarly, people leaders were
coached to identify, analyze, and come up with options to solve the people
problems in their teams and trusted to do so without the People team
needing to be involved in absolutely everything that was happening.
This is just one example of setting the tone for what the People team
are in a startup to deliver and identifying the value of the People team
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in that capacity. However, this lesson for me is broader than that. It’s a
reminder that if you’re not 100% clear on what you’re there to deliver
(and what you’re not), people will fill that ambiguity with assumptions
and guesses based on their own experience. And unfortunately, those
experiences in the People and HR space can be wildly varied and are not
often positive. In the absence of clarity, people make their own.
“I Don’t Know”

It’s human to feel a bit shitty when someone asks you a question and you
haven’t a clue what the answer is. It’s also human to want to avoid the
thought that others around us think we don’t know what we’re doing or
we’re underqualified. Yet it’s these two things together that we’d do well to
embrace, even when it doesn’t come naturally.
To date, I always feel inadequate when someone asks me what we
should do in a people or culture situation and I don’t know the answer. It
took the wisdom of a fair few founders, investors, and trusted mentors to
remind me of two things:
1. In a startup environment, most people are working

it out as they go. We might add a pinch of good
judgment, some lessons from our experience, and
a sprinkle of good intentions. Then we hope for the
best. Every startup environment is different and
playbooks tend to be few and far between for how to
navigate so many different situations. Even this book
is really only scratching the surface of the people
space in startups.
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2. No one knew what they were doing the first time they
did it. It’s a universal truth about starting something
new, be it in any industry or profession around the
world. And the fact we are doing something new is
already a massive learning milestone and how we
can grow our skills.
These two things are part of the fun and journey of building and
scaling startups. It’s usually our own pride that gets in the way of having
a conversation where we’re vulnerable enough to admit we don’t know
the answer. So instead we fill that space with empty words that are, at
best, waffling around without answering and, at worst, a poor attempt at
an answer that may be wrong and dangerous to the startup. I’m guilty of
both, yet even in the moments where I chose to cover up my insecurity,
I realized it did no one any good. I didn’t feel any better in my ability to
waffle out an ambiguous and unhelpful answer. And I certainly never
felt better guessing the answer on my own and allowing others to believe
I knew what I was talking about. I needed to stop pretending and start
accepting those two points earlier.
What has been fascinating to experience as I started to make the
transition to saying “I don’t know” more often is the effect it had on those
around me. It wasn’t met with condescension, at least to my face! Instead,
it became a chance to work together and collaborate. A problem that
needed ideas, debate, advice from others, and a chance to figure it out
together.
Find Your Outlet

A bit of self-love goes a long way, especially in People teams, or in any
role with responsibility for people and culture. You will be part of difficult
conversations that make you feel sick, upset, or guilty. You will see the
best and the worst of people. People will be angry at you because of your
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role and not because of who you are. You’ll doubt yourself over and over.
You’ll be expected to carry an emotional load of stuff that very few people
in the company can see, and if you’re alone or in a small team, the support
network can be sparse.
All of this has a profound impact on our mental health. The very fact
it impacts us simply makes us what we are: human. You deal with enough
of other people’s “stuff,” so it’s vital you have an outlet for your own, for
both your physical and mental health. During the Covid-19 pandemic, my
calendar became full of people wanting advice, support, and often just a
set of ears. Parents who were struggling with school and childcare closures.
People feeling lonely and frightened being unable to leave the house
outside of specific reasons and unable to hook in with their network and
friendships. Folks who were experiencing significant loss and trauma with
elderly and unwell family members and almost no ability to say goodbye.
And, generally, everyone who was struggling to juggle so much happening
in the world with what their work had become.
For months, I was a therapist, friend, coach, counselor, advisor,
listener, and many more hats. And then I would get to the end of the day,
if not sooner, and sit in my shoebox studio in New York alone and go
through some of the exact same stuff myself. I put on too many pounds
to count and was forced to pause almost all of the hobbies and activities
that brought me joy. This isn’t fishing for sympathy. I came through the
pandemic as one of the very lucky ones without significant loss or change,
so I’m very fortunate in that regard. But there’s a parallel into mental
health in the workplace that feels too important, in hindsight, to ignore.
I was trying to be an outlet for everyone else, but forgetting to look after
myself too.
Once some fitness activities were allowed again in New York, I started
to find joy and peace in walking. Sometimes it would be five or six short
walks a day as I needed the change of scenery from my coffee-table-
turned-desk in my studio. When I left a conversation feeling drained or
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worse for wear, I walked. If I felt emotions around the pandemic that
were difficult to contain, I walked. Even when I just felt bored or restless, I
walked. It always found a way to bring me back into a good place mentally.
It doesn’t really matter what the outlet is, just that it works for you and
meets you at that moment where you are. Could be something physical,
something quiet and meditative, something social or something entirely
different. It’s where you go to give yourself some love when you need
it most.
Be Ruthless with Your Time

10:58 a.m. You’re at the end of a call with three of your colleagues about an
upcoming project. James says he’d like to use the last couple of minutes to
discuss something which turns out to be entirely new and definitely not a
two-minute conversation. You begrudgingly go along with it knowing your
11:00 a.m. one-to-one with Kylie is afterward.
11:03 a.m. You manage to escape James who has booked a follow-up
meeting later in the week and you quickly jump up from your chair and
pace to the bathroom for a pit stop before hightailing it back to your chair
to dial in to your one-to-one with Kylie.
11:06 a.m. “Sorry about that Kylie, I’m back to back today and we ran
out of time in that last meeting. You know how it is. I do have a hard stop at
11:30 as I’m speaking to Jesse so let’s dive straight in.”
11:32 a.m. You let Kylie know you’re unfortunately a few minutes late
to your next meeting already so need to wrap up and you’ll give her a call
tomorrow to go through that last item you were discussing.
11:34 a.m. Damn. You open your calendar and see that your only spare
30 minutes at 12:30 p.m. after meeting with Jesse is now taken by your
manager wanting a “quick chat.” Lunch breaks are a thing of the past these
days and every day just seems so busy.
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It’s easy enough to do. Our to-do lists are bursting at the seams; we’re
trying to keep up with what is happening and help others do the same
thing. What starts as a few meetings throughout the day quickly expands
to fill every minute, with our calendar now looking like a completed tetris
diagram. You feel you’re permanently late to every meeting and always
relieved when Gary tells you he has a clash and needs to cancel just so you
have a gap to work on something that was due yesterday. Our calendars
have become our actual job, starting each morning not by identifying what
you want to achieve that day, but by scrolling through each calendar invite
for who you’ll be speaking to that day.
A huge disclaimer coming on being ruthless with your time. Typically,
the more senior you are in the company, the more autonomy you have
over your time. So I wanted to compile tips that would cover the breadth of
roles and seniority that exist in every company, despite being very aware
that a few of these may be harder to implement for some than others.
Reduce Default Meetings to 20 and 45 Minutes

If you’re booking in a meeting with others, calendars default to time blocks
of 30 and 60 minutes. So even if your conversation might be done in 15
minutes, or 40 minutes, you’re typically using those blocks to set your
time aside. We are great at filling the time available in meetings whether
it’s adding value or not. Parkinson would be proud. By changing default
meetings to 20 and 45 minutes, you’re constraining the time to focus on
the value-adding conversation.
Set Meeting-Free Blocks

It’s all the rage for companies to do meeting-free afternoons or days, and
while that may be incrementally helpful, we can’t assume that everyone
will use that same time and day every week to be a productivity ninja. You
also want to avoid the company-wide cramming of meetings into other
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parts of the week as that behavior, on mass, creates a different problem.

Similarly, sometimes the most value-adding work to be completed is in
fact a conversation or meeting, so removing people’s autonomy to do
that is silly. Individual meeting-free blocks can help to create time and
autonomy but on a cadence that works for you. Maybe it’s an hour every
lunchtime to force a break and walk the dog. Or, if you’re in your zone
in the morning, block every morning for an hour or two to use that time
most effectively on what you need to deliver. These blocks don’t have to be
meeting-free. You can absolutely use them for that. But they’re blocks that
are used by what you determine, not someone else.
Confirm the Purpose of Attendance

Overextending invitations for meetings is the equivalent of cc’ing irrelevant
people on emails. It’s not devious, just annoying and unhelpful. If you’re
invited to a meeting, especially when there are over four attendees, where
you can’t see what contribution you will add, politely ask the organizer
to confirm what the meeting is intended to achieve, and if it’s clear you
are just an observer to it, you can offer to help with anything specific
asynchronously or take on any actions assigned to you that come out of it.
Define the Outcome of the Meeting

There’s plenty of literature around about the purpose of meetings and
when and where to use them. It’s never that black and white in practice,
so something I’ve tried to adopt is making sure I’m clear before a meeting
what we hope to achieve by spending time together (where it’s not already
obvious) and if there’s anything that can be shared prior to the meeting
as a pre-read to make best use of the time. This is especially helpful for
“presentation meetings.” Someone has done something and books time to
take everyone else through it. If you want to test a new approach to this, a
week before the meeting, send out either the presentation or document as
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a pre-read, or record a short Loom video of yourself presenting what you

need to, and set the meeting as being specifically to debate or decide on an
outcome. You’ll find it reduces the time needed in the meeting, allows for
more reflection and thoughtful responses during the meeting, and allows
for others to have a greater sense of autonomy for their time.
If You Do Nothing Else, Do These Three Things

This is a really simple habit to help reduce the likelihood you get to the
end of the day and you’re not sure what you accomplished. At the start of
each day, or the night before, decide on the three things that, even if you
do nothing else, you must get done that day. And then test if your calendar
that day allows you time to accomplish those. If it does, great! If not, you
need to reconfigure your calendar (and time!).
Your time is the biggest enabler to how you do your job, so if it’s not
working for you, it’s time to change it. You’re welcome for the pun.
Everyone Is a People Expert

I said these words to a colleague after coming out of a company-wide
forum where I was presenting quite extensive upgrades to a reward and
benefit framework. Weeks of research, engagement, and iteration had gone
into getting something really exciting in place that would scale with the
company, incentivize people, and also continue the journey toward pay
equity. Even though I knew it would be iterated several times once live, I
was pumped to have it in place. Reward conversations and presentations
are always lively, and in this case, it was no different. But from what
started as sharing a new framework that would benefit almost every single
person at the company ended up becoming comment after comment after
comment with sentences starting with “we should be doing…,” “why aren’t
we…,” and “my roommate’s company does it this way….”
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Now don’t get me wrong, I live for lively conversations like these. It’s
gold dust for someone in my role to have ideas and engagement on people
topics. But in the moment that I walked out of that forum and referred to
everyone as people experts, I couldn’t help but wonder what a finance, or
legal, or sales presentation would look like with those sorts of comments
being made. The People space is full of thoughts, opinions, and ideas.
Some of them are from people working directly in that space. But most
of them are from folks who simply have a vested interest in the outcome.
More than any other function in a company, people feel affected by the
decisions that we make. So, quite rightly, we should expect (and want!) for
those decisions to come under close scrutiny.
The missing piece to this is the gap that often exists between those with
feedback and ideas and those who have knowledge and experience in that
area. As a graduate, I remember putting my hand up to complete a reward
analysis project. I’ve always been incredibly fascinated by the concept of
reward in companies and I honestly thought “how hard can it be.” Fairly
narrow thinking I know. In the years since, reward has been a critical part
of almost every HR role that I’ve had in both big and small companies,
and in startups. And the more I work in the reward field, the more I feel
intimidated by just how complex and nuanced it is. I felt more of a reward
expert as a graduate with no experience, than I do as a C-level People
professional with a lot more experience.
It was this gap that would result in someone telling the whole company
that if we’re serious about pay transparency, we need to share everyone’s
salaries within the company, while simultaneously I was receiving private
messages from others, including those in my team, who said they felt
that idea was unwelcome and uncomfortable. How do we balance and
encourage the gift of ideas, criticism, and feedback with the complexity,
nuance, and grayness that is almost every part of people and culture?
The approach I take lies in the communication of what we’re
delivering. It’s not just overcommunicating, but being able to make
transparent almost every single part of the thinking, decision-making,
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and impact of what we’re delivering. We can’t just roll out a reward
framework and then be perturbed, like I was, that others would have
such strong opinions about it. We have to communicate the intent of the
framework, the restrictions, and the constraints that might exist, involve
diverse subsections of the team in the process to design it, explore openly
the imperfections and edge cases, and be brutally candid with how we
arrived at the decision to implement the framework. When we strip away
the asymmetry of information, we’ll still have strong opinions on almost
everything we do, but we can separate these into items needing further
consideration and those that we just need to address head-on.
It’s Great to Experience a Truly Shit

Company at Least Once
Working in a terrible company is truly a bittersweet experience. It’s bitter
100% of the time you are there, and only months or years later once you’ve
left and hopefully found a better company to work with does it start to taste
sweet. And that sweetness is rooted almost entirely in the perspective and
learning that you now have from seeing browner pastures.
I’ve had the good fortune to experience really toxic and unhealthy
cultures, and others that exude values and brings the best out in me. The
perspective and learning from each has been invaluable and helped to
shape a lot of what I now work on. Despite experiencing some really tough
moments and emotions during my tenure in toxic cultures, I’m glad that
they happened.
The perspective I gathered is the ability to identify and be grateful for
positive work cultures and great companies. Take cultural traits such as
belonging, autonomy, and trust. It can sometimes be difficult to identify
traits like these, and the behaviors that drive them, within company
cultures unless we’ve experienced them, in some form, before. My
recognition and appreciation of companies where I feel like I belong is
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driven, to a large extent, by what I experienced and how I felt in workplaces

where I felt I definitely didn’t belong. The pressure I felt to behave in a
certain way, particularly with senior leaders, and the adjusting of behaviors
and covering I had to do to conform to this weren’t as identifiable at the
time. But once I came into a company where this weight was removed,
it became more obvious just how much energy and time I was spending
trying to conform to a culture where I clearly didn’t belong.
Similarly, the learning you take from toxic cultures, and especially
terrible managers, has helped me shape my own leadership approach
and work to avoid the repercussions it creates. In the past I’ve needed
managers at certain times to meet me where I’m at, be it to unblock some
problems I was having, to listen to some feedback, to be candid about
something in the business, and even to just give to show they care about
something I was experiencing. And I know the impact it had on me when
I didn’t have that support from my manager, on both my work and my
general feelings about the company. I never want to have that effect on
anyone in a business.
If you’ve experienced a truly shit company or manager in the past, look
for the lessons in what it taught you, as unpleasant as it may have felt at the
time. Whether you consciously know you’re doing it, the experience itself
has likely given you a heightened ability to sense the behaviors and culture
that you experienced. And, hopefully, gratitude to a truly great company
and manager when they emerge.
caling Part 1: Keep Your Team As Small

S
As Possible
Growing startups are feeding grounds for work creation. Regardless of
how value adding the new work might be, it is a reality of any company
that is growing their product, customer base, and team that the volume
and complexity of work is very fluid for a number of years. Within People
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teams, it can feel like a constant transformation. Small teams without huge
investments in people infrastructure yet are balancing the operational
delivery of their work with one eye on the direction of the business, and
making sure that it’s all aligned.
If you add to this a common investment environment where startups
are receiving an injection of capital every couple of years (usually with
a growth and hiring plan to match), it’s not uncommon to feel that the
answer to work creation is to just keep hiring. However, that’s growth.
Not scaling. And as the business continues to grow the customer and
team base, you’ll start to witness inefficiencies in how the team operates.
Communication becomes more complex and takes a lot longer (picture
the reward framework presentation from the previous chapter and how
that might be different with 500 people instead of 200 people). Work
duplication will start to creep in and, unless the business was already
profitable through the rounds of funding, the inefficiency will be a barrier
to achieving profitability. Culturally, growing like this starts to embed a
problem-solving dilemma. To solve problems, the team thinks the answer
is to hire. But by continuously hiring, you’re increasing the risk of problems
and the impact that they have along with extending the period for which
you feel like you need to keep hiring.
As a manager of a team, I’ve become quite hell-bent on keeping the
team as small as possible for as long as possible. In principle, it sounds
achievable. In practice, it’s a bit of a nightmare. I’ll keep using the People
team as an example for this lesson, but this lesson isn’t company-wide in
terms of the philosophy behind it. It’s applicable across the board.
For a People team to stay as small as possible, two things are
nonnegotiable.
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ork Is Thoughtfully Managed, Not

W
Just Executed
This means that instead of accepting work into the pipeline of things to
be done, the work is swiftly assessed to understand the value, impact, and
approach. For example, you might be asked by a founder to make sure
that any candidate at offer stage has two completed references taken. The
natural response is to make it happen and most companies do that, so why
not? What starts as very manageable, maybe a couple of new hires a month
and two references per new hire, quickly escalates at the next growth phase
to be 30–40 references a month. Add to this the constant follow-up of most
references as it’s never a quick process, plus the administration of obtaining
the reference details, writing up the notes, and storing them on record, and
you now have a bloated work process that keeps growing as you do.
Let’s take a step back from that. Why do you want references to be
completed? Was it the one candidate a founder felt a bit iffy about and
wanted some validation? Is it in a customer contract that it’s required
as part of their diligence processes? What are you trying to achieve from
references, or hoping to avoid?
In over a decade of doing reference calls ad hoc for various roles,
I can count on my hands the number of times the reference provided
insight meaningful enough to contribute to our company’s decision to
hire someone. Only one instance was a genuine red flag, and every other
one was small nuggets of feedback or insight that proved mildly useful. It’s
also risky to assume that feedback from one environment is applicable to
the next. After all, I can provide details of a manager who would sing my
praises and another who would tear me down.
So if we’re going to introduce references for every candidate at offer
stage, we need to consider how and if we want to do this rather than just
jump right in. If it’s most useful for senior roles, should we just consider
references for those roles? If it’s just because of that one iffy candidate,
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can you do references on an as-needs basis rather than across the board.
If it’s an employment verification required contractually with customers
or partners, can we outsource it to a third-party integration to automate
checks through our ATS? If we’re still feeling pressure to implement
reference checks, can you constrain the work to a pilot. Set up a sample of
candidates to have references completed, and then at the conclusion of
the sample, debrief on both the time taken to complete the checks and the
value it added to the company. If it’s justified, great, you have a data point
to extend it a bit further. If not, kill it.
This process of managing the work rather than just executing it is
designed to remove as much work as possible and only keep the most
value-adding part to what you’re trying to achieve. And when you look
back in a year’s time, doing this across all People team processes might
be the difference between a ten-person team and a five-person team, and
potentially thousands of hours of low-value work being completed.
Work Is Ruthlessly Prioritized

Straight off the bat I want to define what ruthless prioritization means.
It does not mean to reorder the to-do list and then go ahead and do
everything. It does mean selecting the highest value-adding work to
complete and stopping everything else. It’s a minor tweak to mindset,
but really important as a scalability factor to allow for teams to stay small
and nimble.
Ruthless prioritization in a People team is about constantly reassessing
the pipeline of work and making a conscious effort to invest resources in
things validated to contribute to company goals. It feeds off the thoughtful
management of work, but is a broader undertaking as this one requires
strong engagement of stakeholders, especially those who influence the
People agenda at the company.
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In one startup, I made a deliberate decision to sequence the

investment in the People space in order to focus on the highest value-
adding work first. We started with recruitment and onboarding, moved
into goals and performance management, built out our reward and
recognition programs, and then went full hog on learning and progression.
All of these are undoubtedly important in a company, but the last thing
we wanted was to need a big team and be simultaneously trying to deliver
all of this work. It would be inefficient and overkill based on what the
company actually needed. This prioritization meant that some initiatives
around were put on ice until other work was completed first, and we
needed to communicate that transparently and sensitively. But this
also allowed for a very small team to deliver all of this work for a rapidly
growing startup and in a sequence that enabled the business to continue
to grow.
Scaling Part 2: Make Yourself Redundant

This lesson is tightly coupled with the last one so it’s both a logical part two,
and also the final lesson in this chapter. This one is personal. It’s a
principle I have set with a number of founders and CEOs I’ve worked with
and helps drive the intent and behavior needed for the role I was fulfilling.
Make yourself redundant. It’s by no means entirely literal, although a
small part of me would be quite proud if that was the case (before swiftly
realizing it means I’m back on the job market!). Making yourself redundant
means an active plan to remove the need of the company to have me or my
role as part of it. For a Chief People Officer or similar role I’ve been in, this
means delivering work in a way that is efficient and automated as much
as possible, building a team that is highly capable of providing the people
experience we’ve been aiming for, a culture that reinforces the behaviors
and traits needed to succeed in a self-fulfilling and self-enforcing way,
and an exceptionally strong leadership culture that aligns all of this with
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their teams without reliance on the People team. Whenever I join a startup
as their first People team hire, it’s because things need building, or are
broken, or just need attention. This principle means that I want to be
so effective in doing what I came here to do, that I’m no longer needed
anymore, and the business can continue to grow sustainably. That’s likely
unattainable and for good reason, as businesses aren’t stagnant anyway,
but it helps as a mindset to avoid accidentally creating reliance or single
points of failure.
There is also a natural alignment with this mindset with our own
well-being in People teams. One of the initiatives I use each quarter is to
reflect on all of the work I’ve been doing and try and think through ways
I can either stop that work, automate it, or build it in a way that requires
reduced input and time. It means I can simultaneously try and create
redundancy within my role and also create capacity to tackle what is
coming next.
Summary
1. Change is inevitable. Make sure you have enough
breadth in your identity and sense of purpose
outside of your job so that if you no longer have that
job for whatever reason, you have enough in your
life to make sure you wake up the next morning with
a sense of energy, purpose, and direction.
2. In new teams and roles, you need to spend more

time than you think building clarity on what you’re
there to deliver and what you’re not. Otherwise,
people will fill that ambiguity with assumptions and
guesses based on their own experience, which can
be difficult to unwind.
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3. In startups, most people are working things out

as they go, and the first they did something they
definitely didn’t know what they were doing. Be
comfortable putting your hand up and saying I don’t
know and use it as an opportunity to work together
to solve a problem.
4. We all need outlets, be it physical, quiet and

meditative, social, or something different, where we
can go to give ourselves some care and love when
things get tough.
5. Protect your time and energy, and be

unapologetically ruthless with your time. Consider
reducing meeting length, setting meeting-free
blocks, ensuring purposeful attendance and
outcomes at meetings, and setting outcome lists for
each day.
6. The work we do in the People space will always

garner strong opinions and perspectives because
the impact can be so deep. It requires deliberate,
transparent communication to bring out our
thinking, constraints, challenges, and approach into
the sunlight so we can explore those strong opinions
in a more constructive way.
7. Look for lessons from terrible companies and

managers. Own your heightened ability to sense the
behaviors and culture that made it terrible, and the
gratitude you’ll have for when you experience the
opposite of that.
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8. Scaling is trickier than we make it out to be.

In the People space, aim to keep the team as
small as possible for as long as possible through
management over execution, and through ruthless
prioritization (i.e., saying no or not yet). Consider
how to automate or remove workload over time to
free up capacity for new challenges.
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CHAPTER 11
TL;DR
T oo Long; Didn’t Read: A Summary of Text
That Was Too Lengthy
I can’t remember the last book I read cover to cover, even if it wasn’t in one
sitting. It’s not because I don’t like books or think books are interesting. I
just don’t have the attention span. Some of the best books I’ve come across
and have on my shelf are ones where I’ve read parts of it at certain points
when I find them relevant, or I’ve carved it up into small chunks over
months. Sometimes, years.
I always find myself craving a better book summary or way to make
it feel more accessible to me. One where I can get the gist of a book
first, before deciding when and where I will dig deeper to further my
understanding. So it feels appropriate in this book that I give that a go for
those readers who, like me, appreciate a TL;DR to pretty much everything.
This chapter collates the summaries of every chapter beforehand into a
single list of mental notes, principles, and lessons shared in People Ops.
Chapter 1: Building from Scratch

• Ground your decision-making in data and make it
transparent. The goal is not to please people. Good
decisions sometimes piss people off.

Chapter 11 TL;DR
• Avoid short-term temptations for bespoke employment

terms. You’ll build a people debt that comes back to
bite you in the ass once you grow.
• Perfect work rarely delivers materially more value than

good work in a startup, so get it done and trust your
ability to iterate it over time.
• Build automation and self-service into as many

administrative processes as possible to delay your need
to hire and reduce administrative burden.
• Be clear on how decisions are made and what inputs

are needed. Decision by committee is neither fast nor
does it result in a higher-quality decision.
• Every initiative you work on must be aligned to the

priorities of the company. Work your way inside-out to
understand what people solutions will solve challenges
and enable success in each team. And beware magpies!
Chapter 2: Leadership
• Identify areas of the company where there is a lack
of leadership capability and accountability, where
the wrong leadership behaviors are playing out, or
where accidental leaders need safety to move out of
their roles.
• Leadership is hard and not for everyone. Embed

into progression and development programs the
option to pursue people and non-people leadership
roles. If you are in a people leadership role, find that
psychologically safe space to share your highs and lows.
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Chapter 11 TL;DR
• We can’t, and shouldn’t, avoid difficult conversations.

It’s human for us to be affected by them and that is not
a weakness. Sometimes those difficult conversations
require us to change tune and show our teeth to get the
best outcome for someone.
Chapter 3: Culture
• Culture is a fluid fabric of systems and behaviors. It’s
how stuff happens, not what’s in the fridge.
• Culture fit and culture contribution are currently

fighting for attention, but it’s never been an either/or
battle. When you’re building your team in a startup,
you need to be looking for both.
• Put a common language around the business and

culture as you grow. It helps you work through conflict,
focus on culture fit and contribution, and build
alignment to goals.
• You can’t be values-led without a significant trade-off

to demonstrate it. Narrow in on the trade-offs you make
that demonstrate what your values might be.
• While process is important at times, overusing it in

growth-stage companies starts to chip away at the pace
and agility that likely differentiate you from bigger
players in the market. Things will slow down and
become more structured at some point, so best not to
force it prematurely.
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Chapter 11 TL;DR
• Reducing the size of your team is a last resort, not a

first one. Exhaust every other option first to reduce
spend, look for ways to reduce staff costs without losing
jobs, and if you need to make that difficult decision
to let people go, your people deserve for it to be done
sensitively and generously.
Chapter 4: Inclusion
• Representation matters, but it can’t be the sole aim of
your DEIB work. Start with inclusion and focus on the
pockets of the business at high risk for non-inclusive
outcomes (e.g., leadership behaviors, communication
and meetings, policies and processes that impact
people directly, such as recruitment, leave, and
promotions). Getting this right adds credibility to the
other work you will need to do.
• When something is 80% formed in your mind, start

sharing it with others for input and feedback. The
remaining 20% will allow for buy-in and prevent
perfectionist behaviors from delaying something that
can deliver value.
• The DEIB space is flooded with good intentions,

but our actions and results leave a lot to be desired.
Intentions are worth nothing. We are accountable
for what we deliver and the impact it has, which
is the standard we should apply to any DEIB work
that we see.
170
Chapter 11 TL;DR
• The gender pay gap has become a divisive topic but is

ultimately a test of so much more in the people space
than just compensation. Getting under the skin of what
drives it, where inequities exist, and how to right these
allows us to tackle the problem at the core, not just try
and manage the symptoms.
• Bias is a normal, unavoidable, and human experience.

We shouldn’t be scared of it or try to deny its existence.
We should be scared of letting it play out unchecked.
Chapter 5: Recruitment
• So many parts of the hiring process are broken. We
have an opportunity to do good by people and offer up
a candidate experience with care, speed, and respect at
its core.
• Best offer first principles can drive tangible results and

reduce asymmetric information in the offer process.
• Reframe hiring to be about hiring someone who is a

great fit for the role, not hiring the best person from the
candidates you’re interviewing.
• Demonstrate two-way interviews by turning the tables.
Chapter 6: Reward
• Build benefits for the 99% of people who will benefit
from and value them, rather than the 1% that
abuse them.
171
Chapter 11 TL;DR
• The status quo of hiring without pay transparency has

passed its expiry date. We need to prevent asymmetric
information and an employer-dominated power
dynamic and reduce the inequities in pay discussions
that prevent our people from feeling recognized,
valued, and fairly treated.
• It is not black and white to simply say no when

someone poses the “pay me more or I’ll leave”
ultimatum. There are reasons why it’s sensible to
counteroffer and scenarios where it doesn’t make
sense, but primarily our goal is to reduce the likelihood
from it happening in the first place.
• Our statutory obligations for benefits and leave are

not our benchmarks for good practice. They are the
bare minimum we have to do and there’s almost never
a compelling reason why we’d ever want to only do
the bare minimum for our people. Similarly, to instill
trust into the relationship with new joiners early, avoid
tenure restrictions on benefit eligibility.
• We need to bridge the knowledge gap on all things

equity, setting realistic expectations, communicating
the key components of equity, and allowing our people
to have access to a transparent and meaningful way to
share in the business’ success.
• Unlimited leave may seem sexy, but it often proves

to have a negative effect. If you do want to rethink
leave entitlements, at the very least it should have
a minimum amount of leave that allows for both
adequate well-being rests and meets any regional
requirements.
172
Chapter 11 TL;DR
Chapter 7: Learning
• Being part of a high-growth startup is a reason to
invest in and focus on learning, not an excuse to do
the opposite. I typically start with the growth and
development culture and nurturing that, nailing
onboarding and building a great team of managers to
amplify impact across teams.
• It can be easy to think of learning as a series of online

courses, conferences, or reading books. But that’s
not where most of the learning actually comes from.
Our approach to learning needs to be grounded
in experiences for people – tackling new projects,
mentorships, learning from mistakes, and stretching
responsibilities.
• Progression doesn’t have to mean promotion, and

it will mean something different for everyone. For
our work in this space to be effective, we need to
understand and tailor our work to how each individual
views their own progression and what they’re trying to
work toward.
• Peer feedback is equally as helpful as it is dangerous.

We should carefully plan how we build skills in giving
meaningful feedback, ensure appropriate and safe
forums in which that feedback is provided, and help
our people know what to do with feedback too.
• Not all resignations are bad. There are great reasons

to leave a business, and when someone leaves who
has aspirations to do things simply not possible in our
business, we should be excited for them and grateful
for their time with us.
173
Chapter 11 TL;DR
Chapter 8: Performance
• Managing a team can feel overwhelming trying to get
everything right and avoid all of the pitfalls you’ve
been warned about. It can be helpful to strip it back to
fundamentals. If you do nothing else for the moment,
make sure you help each person in your team answer
these three questions: What am I doing? How am I
going? Where am I going?
• If you’re building a goal-setting process for the first

time, don’t be afraid to experiment and don’t be
disheartened if you get it wrong. I messed it up a few
times, and with each iteration and improvement, it gets
closer to a great goal-setting process.
• There are two truths about people and startups.

Number one: people outgrow startups. Number two:
startups outgrow people. Both are perfectly OK when
we can’t find a path for someone.
• Swap out your “hire slow, fire fast” mentality for one
that is people-first. Hire with purpose. Design a process
to test the critical requirements and components of
the role that allows for decision-makers to arrive at
a conclusion in the quickest amount of time. Fire
thoughtfully, as though it was you or a member of your
family receiving the news.
• It can be difficult to know what best practice

performance reviews look like, but in my experience it’s
the culture of the business and the manager’s behaviors
that have the most impact on success rather than
the specific design of the performance cycle. Avoid
174
Chapter 11 TL;DR
forced distribution and deferred feedback, identify

and mitigate reviewer bias, and be mindful of how you
define ratings if you choose to use them.
Chapter 9: Remote Working

• The Covid-19 pandemic accelerated decades of
progress with remote work adoption in the space of
12 months. Now that we’ve come out of the pandemic
and greater choice exists, we should expect to be in a
teething period for quite some time as we learn more
about how various arrangements can contribute to our
teams and culture.
• Remote work has broadened our understanding of

how we think about human behavior and performance
in different contexts. It also aired our dirty laundry,
in particular whether we actually know how to
measure performance, how we perceive and build
trust in relationships, and the (lack of ) depth in our
understanding of culture and what drives it.
• Be precise in how you describe work arrangements.
Remote work and flexible work are two different things,
and we should uncouple our thinking on these as being
related.
• A new role has been introduced through the pandemic

in many companies – the remote manager. There
are three areas, in my experience, where remote
managers consistently excel – blending synchronous
and asynchronous communication, onboarding, and
staying in tune with both work and well-being.
175
Chapter 11 TL;DR
• While burnout is prevalent and increasing across all

work arrangements, remote work has added a new
lens to how we identify and respond to unique risks of
burnout that it poses, in particular around the blurring
between our work and nonwork lives.
Chapter 10: Your Career

• Change is inevitable. Make sure you have enough
breadth in your identity and sense of purpose outside
of your job so that if you no longer have that job for
whatever reason, you have enough in your life to make
sure you wake up the next morning with a sense of
energy, purpose, and direction.
• In new teams and roles, you need to spend more time

than you think building clarity on what you’re there to
deliver and what you’re not. Otherwise, people will fill
that ambiguity with assumptions and guesses based on
their own experience, which can be difficult to unwind.
• In startups, most people are working things out as they

go, and the first they did something they definitely
didn’t know what they were doing. Be comfortable
putting your hand up and saying I don’t know and
use it as an opportunity to work together to solve a
problem.
• We all need outlets, be it physical, quiet and meditative,

social, or something different, where we can go to give
ourselves some care and love when things get tough.
176
Chapter 11 TL;DR
• Protect your time and energy, and be unapologetically

ruthless with your time. Consider reducing meeting
length, setting meeting-free blocks, ensuring
purposeful attendance and outcomes at meetings, and
setting outcome lists for each day.
• The work we do in the People space will always

garner strong opinions and perspectives because
the impact can be so deep. It requires deliberate,
transparent communication to bring out our thinking,
constraints, challenges, and approach into the sunlight
so we can explore those strong opinions in a more
constructive way.
• Look for lessons from terrible companies and

managers. Own your heightened ability to sense the
behaviors and culture that made it terrible, and the
gratitude you’ll have for when you experience the
opposite of that.
• Scaling is trickier than we make it out to be. In the

People space, aim to keep the team as small as possible
for as long as possible through management over
execution, and through ruthless prioritization (i.e.,
saying no or not yet). Consider how to automate or
remove workload over time to free up capacity for new
challenges.
177
Index
A mentors/coaches, 147
ruthless prioritization, 162–163
Applicant tracking system (ATS), 65
time management, 153–154
Asynchronous communication, 142
work acceptance, 161
work duplication, 160
B Covid-19, 135–136, 152
Building from scratch Culture
communication strategies, 6–8 autonomy, 35–37
compensation, 3–4 contribution/fit, 32–35
decision-by-committee, 10–12 diversity, 43, 51
decision-making redeployment, 43
process, 3–5, 10 transparency, 34
drive self-service, 9, 10 values, 44
employment terms, 6 workforce-reduction, 40
magpies, 12–14
recruitment process, 11,
70, 71, 126
D, E
unscalable solutions, 8 Diversity, equity, inclusion, and
belonging (DEIB), 50,
51, 54, 55
C
Careers, 147
calendars, 154 F, G, H
communication, 157 Flexible vs. remote working
make-yourself- flexibility, 140–141
redundant, 163–164 hybrid, 140
meeting-free blocks, 154–155 remote, 139–140

P. Caldwell, People Ops, https://doi.org/10.1007/978-1-4842-9819-0
INDEX
I, J, K P, Q
Inclusion, 49 Performance
biases, 60 deferred feedback, 130–131
compensation framework, 59 forced distribution, 129–130
diversity, 47, 50–51 goals and underperformance,
gender pay gap, 55–57 117–118
intentions, 54–55 hire slow, fire fast, 125–127
leadership, 51–52, 168–169 mindset/behaviors, 117
pay transparency, 82–88 OKRs, 120–122
progression, 58–59 outgrowing startups, 122–125
recruitment, 58, 171 rating emphasis, 131
review bias, 130
L, M, N, O
Leadership R, S, T, U, V, W, X, Y, Z
accidental leaders, 22–23 Recruitment, 63
accountability, 19 best offer first, 68–69
completeness, 19 candidate experience, 69–71
development perspective, 24 comparison effect, 73–74
feedback, 28, 29 job application, 64–65
investment, 17, 19 negotiation process, 66–69
progression frameworks, 23–24 transparent salaries, 66
psychological safety, 24–26 Remote working, 135
wrong leaders, 21 burnout, 143–144
Learning, 103 Covid-19, 135–136
career advice, 109–112 culture, 138–139
growth culture, 104–105 dirty laundry, 136–139
onboarding, 106–107, 142 exceptional managers, 141
peer feedback, 113–114 onboarding, 142
perception, 114 performance, 137
perfect-resignations, 115 synchronous/asynchronous
progression, 103, 104 communication, 142
180
INDEX
trust, 137–138 learning budgets, 78–80

Reward, 77 leavers, 96
benefits, 78 liquidation
design, 77–78 preference, 98
dilution process, 96–97 Sam’s story, 88–89
discretionary decisions, 94–96 team parity, 91
equity, 93–94 unlimited holiday, 99–100
global environment, 92 unrealistic expectations, 94
181

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People Ops

Lessons in Culture and

ISBN-13 (pbk): 978-1-4842-9818-3 ISBN-13 (electronic): 978-1-4842-9819-0

Copyright © 2023 by Patrick Caldwell

Chapter 1: Building from Scratch���������������������������������������������������������1

Chapter 9: Remote Working��������������������������������������������������������������135

Chapter 10: Your Career�������������������������������������������������������������������147

Chapter 11: TL;DR�����������������������������������������������������������������������������167

I fundamentally believe in the coming years we’ll see People functions

that’s possible anyway. We’re constantly learning, adapting, and changing

Building from Scratch

• The hiring engine that takes place through “who do we

• Having no onboarding process because great people

© Patrick Caldwell 2023 1

• The employee who earns half of what they are worth

• Justifying the lack of job descriptions with the fact

• The founder who believes every employee who joins

• The promotion of a mid-level individual contributor

• And, my favorite one, believing that they have a

Ground Your Decision-Making

• Expectations: Does it seem right based on what

• Lifestyle: There are two points to this to be mindful of:

• Status and sense of worth: Never underestimate this. It’s

• Fairness: I’ve framed most of the preceding criteria

When it comes to employment terms in a growing company, there is

Done > Perfect

In startups, having something in place that’s about 80% done is of

1. Is the initiative aligned with what the company

3. Do you have a rough idea what success looks like?

4. How will you set expectations? In a number

Decision by Committee Sucks

• Recommendations were coming from people involved

• We did not distinguish between feedback and

• We made a poor assumption that candidates needed

• There was a bit too much desire to please and

• Clarity: Identify the decision-maker who is solely

• Expectations: Set expectations with other team

• Partnership: Establish the People team as a partner to

• Get it done: Make the damn decision! As you will have

• Communication: Communicate the why behind the

Beware the Magpies

 our People Strategy Is Your

• Avoid short-term temptations for bespoke employment

• Perfect work rarely delivers materially more value than

• Build automation and self-service into as many

• Be clear on how decisions are made and what inputs

• Every initiative you work on must be aligned to the

© Patrick Caldwell 2023 17

Red Flag 1: Lack of Leadership

repeatable, consistent success. All of these symptoms point to the need to

• Start at the top: Work with the founders and members

• Accountability: Each role on the leadership team

• Completeness: Collectively, the leadership team

• Leveling: Be conscious of titling as the company grows.

• Fractional leaders: Consider fractional executive

• Relevance to now: Consider the job description of every

Make sure you have a passionate, committed, and capable people

Red Flag 2: The Wrong Leaders

Red Flag 3: Accidental Leaders

Accidental leaders can be inhibitors to growth, but seldom do they

 ot Everyone Wants to, or Should,

1. Progression: Progression frameworks should have a

more senior individual contributor roles helping to

Chapter 1: Building from Scratch��1

Chapter 9: Remote Working��135

Chapter 10: Your Career��147

Chapter 11: TL;DR��167

Ground Your Decision-Making

Done > Perfect

Decision by Committee Sucks

Beware the Magpies

our People Strategy Is Your

Red Flag 1: Lack of Leadership

Red Flag 2: The Wrong Leaders

Red Flag 3: Accidental Leaders

ot Everyone Wants to, or Should,

The Psychological Safety of Leaders

If Difficult Conversations Don’t Affect You,

ometimes to Show You Care, You Need

ulture Is Not Free Beer, Fruit, and a

Culture Contribution or Culture Fit

What Does Autonomy Look Like for You?

Process: The Enemy or the Hero?

ut Only When Is Absolutely

E xhaust Every Other Option First to Bring

E xplore Staff Cost Reductions That Don’t

Do It Right and Look After Your People

Find a Common Language

Ambitions and Goals

Getting Past the Values Fluff

Inclusion > Diversity

e Judged by Your Actions, Not

Get Under the Skin of Your Gender Pay Gap

Area 3: Compensation Framework

The Myth of Removing Bias

espond to Every Single Job Applicant

Start with Your Best Offer and Don’t Budge

our Candidate Experience Is As Important

Turn the Tables