Accelerate Your Leadership

90 Day Plan

By Jeff Perry
More Than Engineering
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Accelerate Your Leadership

A 90 Day Plan for New Technical Leaders

It’s hard to transition from all-star engineer to new team leader. Many of us have been
there and failed hard. Much of that failure comes because we neglect to plan out how
to take on this new, unfamiliar role. This guide intends to help fix that. Experienced
technical leaders will also find this guide useful to revisit their approach and consider
how they can improve. As a senior leader/executive, you can share this guide and with
those you are trying to grow into leadership positions.

Put the Five Factors to the Test

The Five Factors of Leadership and Team Success should be the framework that you
look through in all leadership actions/activities. If you’re not sure what the Five Factors
are, check out my blog post.
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Yes, You DO Need a Plan

There’s no shortage of blog posts, books, and articles about how to manage and lead. I
get that. Yet rarely do they have timelines and checkpoints that are helpful for you to
actually do something concrete. Usually, you are left feeling, “good ideas, now what?”
This plan is different and gives you real actions to take for the next 90 days.

On the other hand, it’s an opportunity for you as a new technical manager to be
introspective and ask if leadership and management is really something you want to do.
Sometimes leadership opportunities get sprung on individuals with no desire to manage
others, or at least little understanding of what challenges leadership will bring. Leading
people means dealing with uncertainty, subjectivity, and feelings – things many
engineers went into their profession to avoid. So as you enter this new chapter of your
career, you’ll have to consider how willing you are to embrace these factors.

Rarely do new engineering managers receive any formal management training. They
often simply learn through observing others or by trial and error. While the school of
hard knocks is a good teacher, it often works slowly.

So I created this 90-day guide to help new technical leaders get through the first three
months by splitting it up into three, one-month phases: Dive into Learning (Days 1-30),
Get Your Groove (Days 31-60), and Personal Assessment (Days 61-90). Before we jump
into the actual process, let’s address some critical things to consider.

Day 0: Know This Before You Start

Many engineers get so caught up in the nitty gritty of technical work that they aren’t
aspiring to be leaders at all, but rather masters of their craft. When someone else sees
the potential and asks them to step up and lead, they have to be willing to make a real
shift and take on a fundamentally different role that moves from technical mastery to
people mastery. You must accept this reality.

Be willing to step away from creating technical work

Technical work is no longer your primary objective and purpose when you manage
other engineers. This is a huge adjustment for many. The longer you hold on to
personally understanding and being involved in every technical decision, the longer it
will take to become a good technical leader. You have a lot of new material and
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concepts to learn and implement. To put it in perspective, most engineers spend at least
four years getting a bachelor’s degree to become an entry-level engineer. You’ll need to
spend a significant amount of time learning to become a good leader. Decide if you’re
willing to step away from creating technical work to do that.

Now, that’s not to say that you won’t be involved in technical work, but as a manager
it’s much more important to review, give feedback, and coach rather than create. It’s
okay and important to get into it enough that you know what people are working on
and can assess their work, but you’ll need to resist jumping in and doing a bunch of
projects yourself, especially to escape your management responsibilities. This may be a
tough transition, and a bigger change than you expect. You may miss the technical
creation and design aspects of your work, and desire to move back into a role as an
individual contributor. That’s fine, and the earlier you can decide what’s best for you the
better.

Be willing to embrace uncomfortable tasks. Those are often the most

important.
Trusting a team with technical details, telling a boss that a project is off track, and giving
critical reviews to team members – these are all uncomfortable experiences that didn’t
usually exist before we became leaders and managers. Yet if we avoid them and slip
back into what is familiar, we pay for it.

You’ll want to support and help your team, and that’s great. Yet it’s important to
recognize the difference between being helpful and removing an opportunity for
someone else to learn. Often the “trust but verify” approach works well – not needing
to see every detail but paying attention to critical project details and providing
appropriate feedback.
Very important: You’ll need to trust members of your team enough to let them run with
ideas that you may not agree with. This is very hard to do for most new leaders but
extending this confidence in someone can be extremely motivating. It may not work
out, but it will turn into a great learning experience for both of you no matter what
happens.

Be ready to manage and communicate in all directions

As a leader, you’ll be managing and nurturing lines of communications in multiple
directions. The most obvious is communicating down to those that you now lead. You’ll
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also have to communicate up to your boss and other leaders. Often the most difficult
lines of communications are with peers and customers (both internal and external). This
is often considered communicating “sideways.” These are often harder because it isn’t
usually formalized through some chain of command but is still hugely important to
understand context and collaborate on cross-functional work. You’ll need to skillfully
work with your fellow managers and avoid any turf battles that may ensue.

Communication comes in many forms – emails, chat, informal check-ins, formal

meetings, standups, collaborative sessions, and more. Goals of communication include
understanding people better and creating opportunities for them to do their best work.
Some leaders work hard to sequence their regular meetings – they have meetings with
leaders early in the week, and opportunities to cascade conversations to their team
through team meetings and 1:1s shortly after to remove information bottlenecks.

For those that you lead, this will need to include frequent career conversations. Asking
questions about career goals and what people are trying to accomplish gives a great
context for how to nurture, lead, and provide chances for them to show their value.
Figure out where people are trying to go and check in regularly about it. If they don’t
know what they want to grow into, this is an opportunity to help them chart a path that
is right for them.

To appropriately manage and communicate with your own manager, you’ll need to be
able to give clear updates on project progress and be able to tactfully push back if you
disagree with your leader. Putting it all together – managing up to the boss, down to the
team, and across to peers should be a high priority to get in place during the first 90
days.

Consider your source of motivation

Jumping into a management job is a huge shift. You now have responsibilities that span
much more than your own personal interests. You are now at least partially responsible
for the effectiveness and satisfaction of others’ work lives. This is a large responsibility,
and you’ll need to know what will keep you motivated through it all.
Here are a few things not to do:
• Don’t manage just to accelerate your career.
• Don’t manage simply because no one else will do it. No need to be a martyr.
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• Don’t manage to please your own manager. You don’t need to take on roles that
aren’t right for you just to make others happy. Be honest with yourself.
Conversely, here are some good reasons to take on a management responsibility:
• Manage if helping others to be better excites you. Think back to previous
experiences of helping junior engineers or less experienced workers. Did you
enjoy this, or was it a burden? When you see someone on the team that is
struggling, are you quick to lend a hand?
• Manage if you are willing to trust others in the same way that you expect to be
trusted. You’ll need to be willing to be vulnerable, ask good questions, and show
that you truly care on a regular basis.
• Manage if you can be empathetic. This doesn’t always come naturally, especially
for a lot of engineers. Think back to a recent conflict – can you examine all points
of view?
There’s a lot to think through and prepare for in the transition to management and
leadership. The quicker you can work through some of these questions, the more ready
you’ll be for your new assignment.

Days 1-30: Dive into Learning

Your first month on the job is all about learning and education. You really can’t learn
enough during this time. Let’s go through a few ideas to consider.

Schedule leadership learning

If you don’t block off time to study and develop your skills as a leader, it probably won’t
happen. This time can be used meeting with mentors, reading management materials, or
taking leadership classes. You’ll then want to quickly take what you learn and practice it
in team meetings, 1:1s, and other opportunities. Learning is most effective when
immediately applied. Don’t hide these learning sessions, however. Own it and make
your calendar transparent. Your team should appreciate this effort.

Here are a few of my favorite management books to get your started:

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Leadership and Self Deception by the Arbinger Institute. This book takes a fictional
narrative approach, helping you be more self-aware and break down personal barriers
we put up in our own leadership.

Drive by Dan Pink. He covers critical sources of motivation for employees that you can
utilize to invite the best out of others.

Five Dysfunctions of a Team by Patrick Lencioni. This book is also a fictional narrative,
taking you through the development and growth of an executive team from
dysfunctional to high-performance.

Dare to Lead by Brene Brown. Brown’s work is all about how to unlock the great power
of vulnerability, and this book applies it specifically to how important it is in the world
of leadership. It might suggest you do some things that are uncomfortable, and that’s a
good thing.

Find a mentor or two (or three)

It’s important to learn from those that have gone before you. If you don’t seek out input
from people with experience, you’re missing out on awesome growth opportunities.
Mentors should be different than your boss, but you can ask your boss for
recommendations. It’s often nice to have a mentor inside and outside of your
organization to offer guidance that is removed from your situation and environment.

Don’t be afraid to reach out to someone you really admire that you think can give you
great advice. Direct requests work best and are most personal. You may be surprised by
how willing and helpful experienced leaders will be. Make sure, however, to be a
contributor in these relationships – don’t just be a “taker.” Take personal ownership for
the frequency and the quality of the meetings you have with your mentors, as they are
giving you their time freely.

Days 31-60: Get Your Groove

With new meetings, responsibilities, and things to learn, you’re going to have to find a
workflow that is conducive to your new role. This will take some intentional structuring
of your calendar and activities. Let’s go through a few ideas.
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Create an “Activity Cycle”
An activity cycle is a checklist of tasks and activities you do on a periodic basis – daily,
weekly, or even monthly. This is about making sure you get to the regular actions that
can easily get overruled by the latest fire. Once again, blocking out time on your
calendar for these actions is most effective. Thus, if you need to reschedule that time,
you’ll be doing it consciously and prioritizing appropriately.

Protect your calendar and cancel meetings

There are a lot of new meetings that you’ll be invited to. There may be some that you
can’t get out of, but it’s worth it to evaluate each one and determine if they are worth
your time. Are you getting critical insights or making connections that you can’t make in
a more efficient way? It’s tempting to accept and say yes to every meeting invite
because you feel obligated, especially when you are a new leader, but if you are
relentless about protecting your time, you’ll be glad you did.

Make sure to give your reports ample time

Even as you are cancelling and questioning meetings, don’t neglect giving time to those
you lead. You’ll want to schedule in regular 1:1 meetings at a cadence that works for
you. They’ll also request ad-hoc time, and you’ll want to be able to give it to them. Best
practice is to do this at the beginning or the end of the day so you can protect large
chunks of focused time for them without interruption during the workday.

Days 61-90: Personal Assessment

This third month is an opportunity to continue to operate with the personal systems
you’ve put in place while also assessing how well you’ve integrated into this new role.
The purpose here is to determine if this is the direction you want to and should take,
and what key improvements you still need to make. Here are a few questions/exercises:
• List each team member. What is unique about each one (strengths, weaknesses,
etc.) and how will you best utilize them and help them grow their career?
• Where are you falling short as a leader – time, skill, motivation, effort? What
needs to be done to improve?
• Can you describe your team’s results? Are they improving, regressing, or staying
the same? If they are getting worse, or you can’t answer this question, that’s a red
flag. You should be able to measure things like quality, progressing through
milestones, and other metrics you define.
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o You may also want to dig deeper into the “why” behind the results.
• How would you describe team morale? What would improve it?
• As a leader, how are you adding value? There may be a critical reason or initiative
that pushed you into your role – are you making progress on that? Look for
improvements that have been made and feel good about them.
• Are you enjoying yourself? You’ll probably be working harder and longer in this
new role, especially at the beginning as you’re learning the ropes. If this is
energizing and you remain excited for the future growth, that’s great. If you are
nothing but overwhelmed and wish you could go back to your old job, then that
may be the best idea. Don’t give up too quickly, but honestly check-in about the
path you’re on.

Day 90: Plan for the Future

Put Day 90 on your calendar. After three months, you should have enough time to
know whether you are on the right career path or now or if an adjustment is necessary.
If this new role doesn’t sound fun at all, it’s important to figure out what needs to
change. Block time to reflect with your boss and talk with him/her about the
experiences you’ve had. You may want to make this clear enough with your boss so
that the whole role is set up in a way that it won’t be devastating to you or anyone else
if you both decide that the right decision is to step away from leadership.

If this isn’t for you, be willing to step aside

Finding out that management isn’t for you should be a good thing, not something to
hang your head about. You’ll want to do the work to decide if it’s not for you now or it’s
not for you ever. Sometimes timing, role, and team just aren’t right or you need more
experience first. People aren’t just born leaders – it takes time and development. If
you’re honest with yourself that this new role isn’t what’s best for you now, it’s best for
you and your company to step aside and find the best fit for everyone.

If you are trying to stay fully technical, often organizations have tracks to continue that
path rather than people management. You can become a senior technical contributor
and often still have opportunities to mentor and help junior employees without direct
management responsibility. You should still have plenty of opportunities to grow and
develop yourself, gaining further mastery of the craft you have grown to love.
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Encourage Truth
It’s important to make sure that people on your team can be honest about giving you
feedback. As individuals we often have blind spots. Others help us see them, so do all
you can to invite others to help you see what you can’t. Encourage this by being
gracious when you get it, not by acting defensive. Not everyone is willing to do this, so
sometimes you may need to find just one or two people on the team who can really
give it to you straight.

Build on strengths of your team members

It’s easy to try and fix problems in people rather than recognizing and building around
their strengths, yet you’ll often find much more success and growth when you improve
their natural abilities. Your team members will be less resistant, and there is often just
more progress to be found in strengths.

Continue to collect favorite leadership materials

Books, articles, courses, and other materials about leadership and management are
endless. Find the ones that work best for you and collect them in a way that is easily
accessible. You’ll want to do this for personal reference, but also for opportunities to
share various materials with those you lead and mentor. Keep making time to learn and
grow a priority.

If you like to lead, there is a lot more to learn

Like any skill or craft, you are never done learning and growing in your leadership.
Getting through three months is just the beginning. It’s an exciting journey!

Be Committed to the Craft

Being a transformational leader doesn’t happen overnight and will take consistent
dedication to stay sharp throughout your career. To be the best leader you can be,
you’ll have to be just as dedicated to becoming a leadership expert as you were to
becoming a technical expert. Perhaps more.

Enjoy the journey and reach out if I can help in any way.

Jeff Perry
jeff@morethan-engineering.com
www.morethan-engineering.com
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