Table of Contents

Section 1
Crossing the (onboarding) chasm
1. Retracing Your Steps to Success 10
2. Making Better People 16

Section 2
Helping your users envision their improvement
3. Selling the Dream 25
4. From “I’m listening…” to “I get it!” 31
5. The Painful Joy of Switching 40
6. The Emotional Tie That Binds 46
7. Providing Rational Ammunition 53
8. Clearing the Runway for Takeoff 60

Section 3
Helping your users achieve their improvement
9. Picking Out the Quick Win 70
10. Planning the First-Run Experience 76
11. Designing for a Safe Landing 86
12. Tailoring the First Impressions 93
13. Driving to Victory 104
14. Creating “Regulars” 115
Section 1
Crossing the (onboarding) chasm

Let’s start at the end: There’s a person that loves you.

!
They use your product constantly, almost religiously. They tell anyone
who will listen how awesome it is at making one particular part of
their life better. If you charge for it, they pay — and happily. If you
don’t, they unquestionably would if you did. They are the least likely
to churn out, and the most likely to pull others in. They’re one of the
best friends your company could have: a thriving, successful user.
!
How did they get there? It’s not like they were born that way. After all,
there was a point not too long ago where everyone on Earth was a
complete stranger to your product, that thriving user included. How
did they navigate their transformation from completely unfamiliar with
your offering to intrigued, to exploring, committing, investing, and,
ultimately, finding satisfaction on the other side?
!
That, in a nutshell, is what user onboarding is all about: guiding the
uninitiated all the way to their own personal promised lands. While
onboarding can’t control how amazing your product is, it can sure as
hell try to get as many people amazed with it as possible.
!
And yet, if you’re reading this, you’re probably not happy with the
current percentage of those who become amaze-ees. How can you
make sure even more strangers turn into thriving users? And while
we’re at it, what the heck is happening to all the ones that don’t?
!
To answer those questions, let’s turn the clock way, way back. All the
way back before a user tries exploring your product, and even before
they sign up for it - in fact, let’s run things so far back that it’s a point
where the user hasn’t yet even arrived on the scene: the time when
the people in your company were hashing out all the decisions that
would result in the way your product is adopted today.
!
For many organizations, those decisions were made by a
combination of two groups: those focused on creating the thing your
company offers, and those focused on driving tons of people to that
thing. Or, as they’re more commonly referred to, the Product
department and the Marketing department.
Typically, the Marketing department’s goals involve driving
awareness, traffic, and signups, while the Product department is
primarily beholden to creating new features & generating ongoing
engagement.
!
Whether your revenue model’s based on subscriptions,
advertisements or “let’s just make this thing really huge and figure it
out later,” chances are very good that getting as much of Marketing’s
traffic to become Product’s engaged users is a very wise thing to do.

? ? ! !
? ? ! !

Marketing Product
And yet, for many products out there, the road from stranger to
thriving user is littered with corpses. A poor user onboarding
experience means countless prospects are left on the table —
prospects whose lives could have been significantly improved by
your product, and who would have happily paid you for that
improvement with their loyalty, referrals, and hard-earned money.
 ? ?
? ? !

Marketing Product

x
x
x
This sucks. It’s a waste of time for the people trying to use your
product, and it’s a waste of resources for the people creating &
marketing it.
!
It means you’re burning advertising dollars on prospects that would
otherwise be a sound investment, and it can lead to low retention
rates even for those who do make it through. Factor in the extra
support & sales costs to hand-hold an unnecessarily confused user
base through your adoption process, as well, and it becomes clear
just how much cash you’re bleeding because of it.
!
If your company exists to change the world, crappy onboarding
means it’s changing a lot less of it than it could be. In that way,
humanity is poorer for it. And as a business, your company is literally
poorer for it.
So, let’s fully explore that jump from stranger to thriving user, and set
each moment of it up for outstanding levels of success. While every
product will have its own unique progression, let’s take a walk on the
wild side and play fast & loose with some generalizations.
!
Here’s a very generic outline of a usual customer journey:

Advanced use

Ongoing use

Purchase

Recurring use of product

First use of product

Sign up process

Introduced to product

We will get into these steps in WAY more detail in their own time, but
all we need to know right now is that more and more prospects are
dropping off with each subsequent step, and that it’s especially true
for steps that aren’t actively being managed.
!
Take a gander over each one, and think about who in your
organization “owns” advancing users from that step to the next.
If yours looks something like this, you are definitely not alone:

Product!
Advanced use
Customer
Ongoing use
Support??
Purchase

Recurring use of product

First use of product

Sales??
Sign up process

Introduced to product

Marketing!
This is quite a gap to cover. Count in all the OTHER things the
Product and Marketing departments have to worry about, and the
likelihood of a kick-ass onboarding experience “just happening”
approaches zero.
!
Wherever you happen to reside in your organization, bridging this
gap will require serious dedication. If you aren’t vigilant, you’ll wind up
dropping new users into the proverbial jungle with only a knife
between their teeth, leading to few finding their way out unscathed.
Actually, an even better metaphor than a jungle is a steep, craggy
mountainside, because this is a climb — you’ve got to overcome
forces like apathy and distraction working against you every step of
the way:

Fortunately for your users, though, they have you to help make that
climb as painless as possible. By planning the easiest route,
removing as many roadblocks as possible, and providing timely
encouragement, you can “sherpa” them and your business to new
heights.
!
So how do you plan out that route?
Chapter 1
Retracing Your Steps to Success

It’s probably been a while since you signed up for your own product.
In fact, I’d wager it’s been a while since anyone at your company has
(not counting QA, anyway).
!
You all eat, sleep, and breathe the value your software provides, and
have explored every feature inside and out. You’re the very definition
of “power users”. In fact, you probably know more about the space
your product serves than most of your own clientele. What would
ever compel you to go back through your earliest tutorials?
!
Well… yeah, exactly. I may be misquoting it a bit, but there’s an old
adage that goes something like “You are not your users, and you are
especially not them when they’re first trying to figure out what the hell
it is that your product does.” *

Ironically enough, your product’s first few

impressions are SO make-or-break that
you simply can’t afford to evaluate them as
the expert that you now are — you have to
try to forget everything you know and
???
come in with a totally fresh perspective.
This is also known as the “turn yourself
into the guy from Memento” strategy.**

In order to start retracing the steps, let’s try going back to the top
places someone might first find out about your company and then
map out all the things they go through in becoming a highly-engaged
user (and beyond).
!
For example, let’s say your product is a SaaS offering for customer
support, and cost-per-click ads are one of your primary acquisition
channels (places where you get new users). Looking at your site
traffic, you see that your Google AdWords conversions for “customer
support knowledge base” is doing particularly well for you, bringing
in tons of new signups every day.

* Not an actual adage.

!
** Not an actual strategy. Please do not attempt.
Super! Not only do you have a steady stream of prospects, but you
know exactly where to go to find their introduction to your company
— just do that search yourself!
!
Sure enough, searching for that term in Google turns up an ad for
your site in the right-hand column.

The ad’s link points to a landing

page (a page designed for people
to “land” upon… I know, right?!)
with more information on the topic.

Super Easy
✓ Knowledge Base!
If you’re sick and tired of
knowledge bases that are
a total pain to set up, you
should really think about
giving ours a shot.
! At the bottom is a big
It’s super EASY to set up!
button, which links to
your pricing page.
Learn more!
 Plans & Pricing

Standard
Rookie Pro!

The pricing page has a

CTA (call to action) for
$20/mo $100/mo
$40/mo starting a free trial,
which links to a page
Start a free trial! with a signup form.

Sign Up! Now!

In turn, the signup form

triggers a confirmation Get Started!
email.
 Confirm your address!

Click to confirm!

Either that or paste this into your browser or something:

http://yoursite.com/2903u2093429384-23841098

And just like that, you’ve outlined five key touchpoints (things that
people interact with in relation to your product) for getting someone
from square one all the way into your application!
!
Also, notice how two out of the five weren’t even parts of the
hypothetical website — the first was an advertisement, and the last
was an email. Don’t forget that your onboarding experience doesn’t
necessarily start or stay at YourCompany.com!
!
Keep going through the entire setup process, documenting every
step that’s either required (like confirming an email address) or seems
super important for getting value out of the product (in this example,
“adding your logo to your knowledge base” might be one). It’s ok if
things get a bit fuzzy as you go on — we’re just trying to get the
general shape of things.

PRO TIP
If you want a quick way to see all the pages your site makes available, go to Google and do a search
for “site:yourdomain.com” (where “yourdomain.com” is, well, your domain) and it will show you
everything it has indexed!
Once you’ve documented all the touchpoints for one end-to-end
customer experience, go back and do the same thing for all the
other top entry points. For example, if you’ve already documented
the acquisition path for new Google AdWords users, go back and
document how getting started is different for people who arrive via
your “refer a friend” feature. Rinse and repeat!

Pricing page Email confirmation

AdWords ad

Getting started
Signup form
Landing page

PRO TIP
While you’re documenting all of the touchpoints, also evaluate them for consistency with each other.
For example, did the description of the Google search result match up pretty well with the content of
the landing page it pointed to? Be mindful of what your users are pursuing at each step, and help
shape their expectations for the next one. UX pros call this “maintaining the scent of information.”
Chapter 2
Making Better People

Alright! Now, that you’ve mapped out all the touchpoints in your
current onboarding workflow, let’s make like dreamers and imagine
what your ideal one might look like.
!
When approaching this, it’s really, really important to remember that
people do not use software simply because they have tons of spare
time and find clicking buttons enjoyable. They use software because
it significantly improves their lives in some way.
!
For example…
Do people use Wistia because
they enjoy embedding videos,
because they like filling out
or because they like being
personal profiles, or because
better at video marketing?
Do people use OKCupid Do people use Netflix because
they enjoy streaming video, or
because it makes them better at
they want to be better at relaxing after a hard day?
dating?

In that sense, it’s tremendously helpful to think of onboarding not in

terms of activating features, but in terms of how your product makes
its users successful. Put another way, you earn their engagement by
making them better people, not simply by making a better product.
!
For that reason, your onboarding experience shouldn’t be defined by
the touchpoints you create, but instead by the improvement you
provide. It’s not about getting people from Point A to Point B in your
app; it’s about getting them from Point A to Point B in their lives:
better video marketers, better daters, better relaxers. That’s the
recipe for loyal, ongoing engagement.
!
Take the time to get very clear on what kind of “better people” your
product makes. It will inform everything that follows from here, so it’s
super important to get right.
!
Good definitions generally tend to be a single thing. If your definition
includes multiple items, there’s a fair chance you’re simply listing your
biggest features, and not the overall benefit they provide. That’s
recursive thinking (“we make people better at using our app!”), which
you want to avoid, big-time.

For example, a note-taking app

like Evernote might say “we
make people better at writing,
storing, & searching for notes,”
but that’s really just describing
the use of the product. People
might want to be better at those
activities, but to what end?

Something like “we make people better at remembering things”

could hit much closer to their users’ main aspiration.
!
It can still be hard to separate out the benefit of using your product
from the features you’ve created to accomplish it, but here’s a litmus
test that can really help keep the two straight:
!
Remember playing Super Mario Bros. as a kid, and seeing a fire
flower pop up? You weren’t excited because it had a green stem or
because you could get it simply by walking over it — you were
excited because once you got it, you could hurl fireballs!

PRO TIP
If your product’s main benefit is entertainment instead of productivity, it still totally qualifies for this
approach. Even the most “frivolous” games & social apps fulfill some otherwise-unmet human need.
This is an equally-important part of being human, and one well worth crafting an onboarding
experience around!
The product (the fire flower) and its characteristics (green stem, easy
to pick up) were not the sources of excitement. That came from
knowing how kick-ass you were going to be once you got it.

This isn’t what you sell

This is
You want your entire onboarding experience to be aligned around
that kick-ass-ness. Every step along the way should help boost
people towards the fireball-throwing beast they want to be. Look
back on each of the touchpoints you noted in Chapter 1 — how do
they measure up in that light?
While you’re looking them over, also remember who’s in the driver’s
seat at every turn: the user. Content and interfaces do not generate
user actions, they simply facilitate it. It has to resonate with the intent
the user’s bringing to the experience.
!
Want a non-software analogy to illustrate the concept? I got your
back!

Non-software analogy to illustrate the concept

Let’s say one of the cable giants messes up your bill, and you call their 800 number to correct it.
You’re presented with the inevitable “please listen carefully, as these options have changed” greeting,
and are then told that pressing 1 can get you to Sales, 2 will go to Upgrades, and 3 will help you
bundle additional services onto your plan.

!
There isn’t a person alive that would say “well, I came here because I’ve been overcharged, but yeah
I guess it’d be pretty cool to add a landline, instead” — you want that billing problem fixed! The
company could list all the things they want to happen until the cows come home, but they all might
as well not exist unless one matches what you want to happen.

So it goes with web experiences — the user is in charge, and if the

options you give them don’t get them where they want to go, they
won’t be used. It only works if you first identify the intents, and then
craft things to support them as fully as possible.
!
When you design for intents, you harness the only source of energy
driving a web experience — the user’s motivation to move forward.
You make the pathways, but they’re useless unless the users want to
walk down them.
For each touchpoint, try to really put yourself in their situation —
what’s important to them at that particular time? What just happened
that prompted them to start? Where do they hope to head next?
What other information might they need?
!
It’s kind of like designing in “3d” — you’re not assessing touchpoints
as items in isolation, but rather as a coordinated series of
experiences, each propelling the user forward by serving their
immediate interests. Beads on a necklace. Steps in a dance.
Movements in a symphony.
!
And it ends with them becoming better people — the kind of people
they want to be! How cool is that?
!
The whole rest of the book focuses on completely nailing the
touchpoints of every major phase.
!
I’m excited. Are you? Let’s do this!
Section 2
Helping your users envision
their improvement

Remember that mountaintop we were

helping people scale? The one where
the super-awesome, improved version
of themselves was at the top?

Well, there’s kind of a problem. While our towering, Zeus-like

perspective lets us see the entire onboarding pathway at once, the
users in real life are mostly limited to going off of whatever screen
they’re seeing at that particular time. They might have a hazy idea of
what could be coming next, but that’s about it.
To complete our analogy, let’s make it… like… a super cloudy day.

Hey, what the heck

am I doing here?

Of course, no one’s going to start climbing a mountain without ample

motivation for doing so, and that also goes for any onboarding
experience — after all, even the breeziest ones take some effort, and
no one goes through them just for funsies!*

* Present company excluded.

In order to get them to begin their ascent, you have to give them a
good reason for doing so! Fortunately, you’ve already defined that
!
“better version of themselves”, and nothing motivates quite like self-
interest.
!

Oh, I get it!

?
!

Our first move is to confidently and credibly tell them how much
better things will be at the top, and use that promise as a motivator
throughout the entire journey..
!
Let’s get started.
Chapter 3
Selling the Dream

Let’s start at the initial contact — the first time someone comes
across something your company has created. It might be a search
result, or a banner ad, a blog post, or your home page itself;
whatever it is, this is your first impression, and you want it to be a
good one!
!
These earliest touchpoints might typically be considered “marketing”
and not “onboarding”, but how successfully can you onboard
someone when they start things off with a misaligned impression of
the value your product provides? If your product offers bookkeeping
help, but people are signing on thinking it’s project management
software, they’re doomed from the start — no wizard or product tour
can save that.
You’ve gotta plant that seed of future value consistently from the very
earliest stages - not only for motivation, but for orientation, as well. To
put it another way, think of onboarding as less of an interface
problem and more of an interpersonal one. You’re progressing a
relationship, not just introducing a UI, and it’s never too early to start!
!
Articulating your value clearly lets people know if this relationship will
work for them or not right away, without having to muddle through a
confusing experience to find out. It can also help lower churn (the
percentage of your regulars who stop using your product) by quickly
screening out the people who shouldn’t be signing on to begin with.
!
It also lets you focus more of your time and resources around
providing outstanding service to users who should be in there! It’s a
win-win for everybody!
!
So, how do you introduce yourself well? What key information do you
need to provide to get them to take that first crucial step? This may
come as a shock, but I’ve found that communicating in terms of how
much better their life will become can be a pretty effective approach!
That is to say, talk about them, not you.

PRO TIP
The VERY first impression someone has of your company could easily have occurred before they
encountered anything you directly created. Word-of-mouth from friends or colleagues, a random
comment on Twitter, getting mentioned in a news article, etc. Since you’re not in total control of those,
though, I’m leaving ‘em out. That’s not to say you shouldn’t try to have some positive influence over
how others describe you - you totally should! I just gotta draw the line somewhere, people!
Going back to the fire flower analogy, which page do you think would
lead more people to click the “learn more” button?

This Thing Is You Can Slay

Totally the Best from Far Away!

Recognizable by its patented green Stop using your tiny, delicate body to
stalk, the Fire Flower™ is the latest in duel with your foes — kill them with
weaponized plumber technology. fireballs from long distance instead!
! !
Its patented Dual Leaf Composition™ Our flower also makes you HUGE, so
provides an optimized method for even if you’re a little reckless, getting
consumption — to install, simply walk hit doesn’t kill you — you just shrink
over its icon and setup is complete! back down and keep on rolling.

Learn more! Learn more!

Might it perhaps be the one where it tells them they’re about to

become FREAKING AMAZING??

PRO TIP
If you’re thinking that describing things in user-centric terms can’t apply to your company because it’s
B2B, sorry Kemosabe, but you’re straight-up wrong. Every step of the way to purchase, there are
humans — impressionable, self-interested humans — able to promote or hold back the sale. On top
of that, it’s incredibly easy to tie improvements directly to ROI when business is involved: who
wouldn’t want a salesman who’s twice as effective at finding leads, or an administrative assistant who
needs 6 fewer hours per week to order lunches?
People want to know how your product will be a meaningful addition
to their lives. Establishing your product’s value in its attributes
(features, performance, etc.) forces people to piece that meaning
together themselves. That’s tedious for them and risky for you —
how do you know their interpretation will be accurate? When you
instead talk in improvements, you’re handing them a complete
picture, not a puzzle to put together.
!
Think of your entire onboarding experience as a heroic story, with
your user as the star. You know how awesome Daniel-san was at the
end of Karate Kid? Raised up high on cheering shoulders, trophy
proudly held aloft, his crane kick having vanquished his hated rival?
You lead with that.
!
Apologies to Mr. Miyagi, but you do not lead with “wax the cars and
sand the decks, and then we’ll see what happens.” You start with the
end (kind of like this book did!). This is the hook that will pull your
users all the way through the p.i.t.a. they’re about to subject
themselves to.
!
This is the narrative thread that must be woven into every touchpoint
in your onboarding experience. This is the dream you’re selling.
!
That said, you don’t want to go full “khakis & laptop on a tropical
beach dream” on them. That’s way too vague. This isn’t about selling
something as generic as “the good life,” it’s about holding up a mirror
to your users and showing them an improved version of themselves,
in one clear and specific way — the way your product helps them.
!
Also, don’t shy away from being comprehensive in articulating that
improvement. You don’t want to blindly follow the lead of the
Twitters, Facebooks, and LinkedIns of the world, with their spartan
pre-signup touchpoints. They have the enviable position of
presuming most everyone who comes their way already knows what
they offer. Unless you’re truly a household name, that’s a very risky
assumption to make.
!
I know, I know, they’re wildly successful. It’s hard to ignore out of
hand any approach they’re taking. Fortunately, you don’t have to
take my word for it! Josh Elman played a large role in growing the
user bases of *record scratch* every single one of those companies!
Hear what he has to say:

“Most people have heard of Twitter, so we get the luxury

of having a blank home page that just says ‘sign up’ — I
actually don’t encourage this for most sites early in their
stages, because most people who come to your sites
have no frickin’ clue, and they’re not just gonna sign up
without some rationale. Just be careful not to copy the
people who are much, much larger.” — Josh Elman
Of course, the comprehensive description of your product need not
be limited to the home page alone. As mentioned before, landing
pages can do an absolutely terrific job of rounding out the full picture,
particularly by focusing in on one specific aspect geared towards one
specific user segment.
!
Landing pages also thrive when you need to quickly throw something
up there and see how it performs. They’re ideal for rapidly testing
theories about how to describe the value you provide, and in that
sense are kind of the pawns of the product design “chess match” —
they’re cheap, numerous, and relatively disposable.
!
If you’re finding difficulty in getting lots of landing pages up,
Unbounce has created an amazing product for doing so not only
quickly, but totally without the need to tie up engineering resources. If
you pair them up with Crazy Egg, you can really ramp up your
feedback loop, which will turn your landing pages into heat-seeking
missiles of mutual success. I highly recommend them both!
!
Either way, take a look at all your touchpoints, especially the
introductory ones — are they promising an improvement? Are they
announcing super powers, or just describing features?
!
At every step, you want them selling the dream as comprehensively,
accurately, and persuasively as possible. But even that is not enough
on its own — in order for them to take that leap, they have to first
believe it will actually get them to where they want to go.
Chapter 4
From “I’m listening…” to “I get it!”

There’s a phenomenon in the software business known as the “aha

moment” — the point where the clouds suddenly part for the user
and the high-level benefits and abstract notions you’ve been
preaching immediately become startlingly, excitingly clear.
!
“Oh, I get it!” you may hear them say, “So I just fill out this form and
instead of having to walk my expense receipts three floors down to
Jane in accounting, she just gets them in her email? I love it!”
Suddenly, the vague has become personalized. Everything just…
clicks.
Sadly, this “aha” moment usually comes way too late. It’s often only
unlocked by either a significant amount of futzing around in a trial or
a high-touch, resource-sucking live product demo. That’s
unfortunate, because the majority of your audience will never make it
that far.
!
Blind faith is not a desirable requirement for advancement through
your onboarding experience: if your “aha moment” comes deep
inside your product, you’ve already lost.
!
What if you could instead generate that “aha moment” before signup,
when it can happen for many more people? How could you create
the mental connection of how your app will get them to that desirable
place, without having to pull them all the way through it to figure it
out?
!
The key is to get them to understand your product in the context of
their own lives. “Wait, I can rent movies without going to the video
store?” “Hold on, I just drag my files into this one folder and they’re
automatically on all my devices?” “Whoa, I can have super strong
passwords without having to remember any of them?” *

* Notice how all of those epiphanies use the word “I”? Everyone’s the hero of their own stories. Don’t
forget the power of “whoa, I…”!
Ideally, your pre-signup touchpoints allow your users to envision not
only the improvement you provide, but also specifically how your
product helps them get there. The home page for the mobile app
POP (Prototyping on Paper) does this flawlessly.

They start with an extremely

clear value prop, placing it
directly within the context of an
activity their core audience is
already very familiar with —
iPhone prototyping.
!
Next, they dive straight
into describing the real-life
workflow the app facilitates.

Notice how the first step (“Design on Paper”) doesn’t even take place
in the app at all? Instead of describing their product’s screens,
they’re anchoring their value around how their product assists the
bigger, more relevant thing the user is ultimately trying to accomplish.
They then describe all
three of those steps in
detail, explaining exactly
where POP fits into the
process, and specifically
how it enhances it.
!
This makes it SUPER
easy to arrive at the
realization “oh! I can get
the speed of paper
prototyping without
having to sacrifice the
in-device experience?
Count me in!”
!
“Aha moment”:
unlocked. And roughly
30 seconds into the
home page, no less!
In fact, I could storyboard the entire experience just by going off their
home page alone, using “I want to watch people use my UI idea” as
a starting place:

I create hotspots in the I get to actually watch

I sketch out wireframes I use my phone to take
sketches that link to
other people tap around
with pen and paper photos of each sketch
other sketches on the paper prototypes!

The power here is that I can easily visualize what my life will be like
with the product in it, so I can contrast that with what I’m currently
doing. It’s actually 100% ok if my understanding of the UI is pretty
hazy at this point: the features aren’t the star — how they fit into my
life is.
!
In POP’s case, I don’t need to know how the hotspots are created, I
just need to know that they are. In fact, this is the exact opposite of
outlining the workflows inside the context of the app — it’s showing
the app’s place inside the context of real-world workflows.
!
This even works for non-software products. Here’s a storyboard for
using Swiffer, starting with “I have a mess I need to mop up”:
 I pull out one of those I put it on the end of my I mop up the floor that I throw the wipe thing

wipe things from the box Swiffer mop needs moppin’ in the trash, mess gone!

This makes it super easy for me to mentally contrast that experience

with my current, non-Swiffer-y one. “I don’t have to lug around a big
bucket, get my clothes sloshed with filthy suds water, OR have to
figure out where to store a damp, smelly germ magnet? Take. My.
Money.”
!
If your earliest touchpoints sell the dream, your following ones should
help ground it in reality. A high-level value proposition like “the best
way to publish your social media updates” might be intriguing, but if
you then fail to answer even a simple question like “ok, how?”, the
whole thing quickly unravels.
!
Instead, consider how legitimized that value prop becomes when you
follow it up with something like “you save your updates as drafts with
us, and we publish them on your behalf at the the exact best time for
your audience.” You just went from “dubious claim” to “Buffer” in 24
words!
A particularly popular way to help people connect the dots is to use
what’s typically called an “explainer video”. This is a 1-3 minute video
wherein, unsurprisingly, you explain your product and the value it
provides.
!
A lot of times, they’re animated, but sometimes they’re live-action
and star Adam Lisagor.

As a medium for communicating the central value of your product,

video has a lot going for it. For one, it’s narrative-driven by nature,
which means you get to craft and control how your story is told,
rather than hoping the user will sleuth things out correctly on their
own.
Video’s also a dual-channel experience. Instead of having to cram all
your messaging through the visual channel (with text and imagery
only going through their eye holes), you get to double your
bandwidth by going in through the ear holes, as well. This lets more
parts of the brain take on more detail about what you’re explaining.
!
Lastly, it’s no secret that web browsing can be a tedious activity at
times. It’s certainly not digging ditches, but having to constantly
orient yourself on a new page, hunt for a sign of what you’re looking
for, click, then reorient and repeat can become a low-stakes grind.
!
When someone clicks on a video, they instantly switch from an active
browsing mode to a passive viewing mode and their brain gets to
kick up its heels and simply let the video do the work.
!
However, explainer videos can also be crazy expensive as compared
to vanilla web content like copy and images, and are way less easy
to adapt on the fly.* They’re also no better than the story that they
tell. If you can’t sell people on using your product in person, for
example, replacing yourself with a video isn’t going to suddenly make
things click.

* Wistia’s analytics can make it much easier to tell which parts of a video are falling down on the job (for
example, if people drop off long before it’s over), and I wouldn’t launch an explainer video without them.
Of course, changing a video based on that information can still be quite resource-intensive!
And ultimately, that “click” you’re striving for is really just a mental gap
being bridged. It’s the user tying your abstract claim to something
concrete they can relate to.
!
No matter what medium that click-inducing story takes, make sure it
reliably acts like stepping stones of belief, transporting their imagined
self from the situation they’re now in to a much more desirable one.
!
Based solely on your earliest touchpoints, how fully can someone
articulate their new behaviors once your product is in their lives? How
clearly can they envision your product getting them to success?
!
If your pre-signup touchpoints aren’t shepherding someone to that
“aha moment” on their own, go back and rework them until they do
— hoping your product will save your butt later on may be far too
costly!
Chapter 5
The Painful Joy of Switching

Even once your prospective user can imagine their way to becoming
better with your product, there’s still one major force in play
preventing that from actually happening: the way they’re currently
addressing the problem your product solves.
!
Whatever human need your software fulfills, you can bet your visitors
are already satisfying it, one way or another. Unfortunately for you,
people tend to dislike change, especially when they’re the ones that
have to start doing things differently. Getting them to switch is a very
tall order — you’re going to have to peel them from what they’re
already doing as if they were wearing a velcro suit.
There’s a really helpful mental framework for changing up human
behavior called “The Rider, The Elephant, and The Path.” It was
initially introduced by Jonathan Haidt and later popularized by Chip &
Dan Heath in their book Switch: How to Change When Change Is
Hard (they also were the ones to add the “Path” part).
!
The gist of the concept is that your psychological makeup has two
main sides: the “Rider,” which is the rational, big-picture part of your
mind, and the “Elephant,” which is the emotional, impulsive part.

Direct the rider

Motivate the elephant

Prime the path

PRO TIP
Don't assume your only competitors are companies that make products similar to yours. In fact, it’s
much more likely that your users are currently solving their problem with something they've cobbled
together themselves, and are only now seeking outside help because they’ve stressed their own
system to the breaking point. In that way, your true field of competitors widens to such ingrained
incumbents as pen & paper, telephones, email, and Excel. Considering the fact that we’re also dealing
with an extremely limited amount of attention to make our case to, let’s throw showstoppers like
apathy, confusion, and the back button into the mix, as well. Gulp! (also, see appendix for more info!)
The Heath brothers describe it best:
Perched atop the Elephant, the Rider holds the reins and seems to be the leader. But the Rider’s
control is precarious because the Rider is so small relative to the Elephant. Any time the six-ton
Elephant and the Rider disagree about which direction to go, the Rider is going to lose. He’s
completely overmatched.

For example, your “Rider self” may want to save up money in the
long term, but your “Elephant self” might see the latest iPhone and,
well, suddenly that savings plan can wait.
!
The key is to create touchpoints that orient the rational Rider in the
right direction, while harnessing and guiding the urges of the
emotional Elephant. You also want to shape the “Path” — the
environment they’re traveling in — to support forward progress as
much as possible.
!
Since the Elephant stuff is so much more powerful, let’s tackle that
first. When dealing with emotional forces, appeals based on logic
and reasoning aren’t very effective. Humans are irrational beings, and
the non-rational side of the human psyche is, well, super not rational.
!
Ultimately, what you want to accomplish are two sides of the same
coin: you want to connect with them by showing you understand
their current struggle, and you want them to forge an emotional
connection with the superior option you provide.

RED ALERT!
I should mention now that working in the medium of people’s emotions is some potent stuff. “Black
hat” approaches here can seriously backfire, and even when successful are ethically questionable at
best. Please remember that you too must live in the world you create around you.
In order to empathize with their situation, you have to really try to fully
understand it. If you’re not already, get as much contact with your
customers as you can, in any way you can. Services like Qualaroo for
on-site surveys, and Olark and LiveChat for, well… live chatting make
for great ways to get the customer-contact ball rolling.
!
Ultimately, though, there are TONS of ways to spend quality time with
your users (screenshares, interviews, emails, customer support,
surveys, etc.), and the best option for you is whichever one provides
meaningful conversations with the most users the fastest.

“I’ve found that really good products are very good at

listening, and the more you’re able to listen and let
people talk, typically the better.” — Brennan Dunn

Customer development and user research are topics more than

deserving of entire books in and of themselves (see appendix for
some great ones), but the central notion is this: no amount of clever
marketing tricks, product design patterns or UI trends will ever
outperform leveraging the basic knowledge of how your audience
perceives their current situation, and how they would like it improved.
Learn it. Love it. Live by it.

PRO TIP
One great way to speak straight to your audience’s hearts is to record what users say in one-on-one
interviews, then use those words verbatim to communicate at scale to untold numbers of others just
like them.
As your knowledge of their self-perception grows, look to address
their most significant points of struggle and anxiety as directly as you
can.
!
If your product is project management software and you find out your
customers are concerned with administrative overhead,
acknowledge the nightmare that group emails can cause. If they
admit they hate constantly wrangling multiple versions of files, tell
them you know what a pain email attachments and shared Dropbox
folders can be.
!
And at the most advanced, address those points of realization right
where they arise — if as soon as someone sees that you offer file
storage they wonder how secure it is, tell them right there!
!
Banish FAQ (Frequently Asked Questions) pages from your website.
People only find them useful when their questions aren’t already
being answered in the place they arose. The end goal is not to
quarantine frequent questions, it is to address them so thoroughly
that they’re no longer being frequently asked in the first place.*

* If you must keep your FAQ page, at least rename it to something more honest, like “QtRoOSFFtA”

(Questions the Rest of Our Site Frequently Fails to Answer).

Ultimately, you want to play the role of a dentist picking at the raw
nerve of a rotten tooth — poking their Elephant’s awareness of the
less-than-optimal situation until its previously-unmovable inertia 180s
into a relentless force for self-improvement.
!
Since their current situation isn’t suiting their needs (that’s why
they’re coming to you to begin with), and with it looking a lot less
sustainable by the minute, we can present an alternative that looks
even more attractive by comparison.
!
However, getting the Elephant riled up and wanting to flee its current
situation doesn’t do either of you much good if it’s not directed
towards something that’s a better replacement. Fortunately, you’ve
already aligned your product, experience, and onboarding narrative
around improving your users, so that stage is already set!

PRO TIP
If you’re seeking a time-tested shortcut for understanding the slings and arrows of switching up
product allegiances, look no further than your company’s customer support department. Not only are
most tickets filed when users are getting acquainted with a product, but few in your company know
the end-to-end user experience quite like customer support agents: they catch hell from all angles.

!
In fact, when picking a user onboarding champion within your company, don’t discount pulling
someone from the ranks of customer support. June Lee of MailChimp put it quite succinctly: “Support
people have pretty good knowledge of how the app works, and they also have a lot of experience
dealing directly with customers, so they get a lot of customer feedback, as well.”
Chapter 6
The Emotional Tie That Binds

Now that you’ve peeled your users from the thing they were stuck in,
you want to superglue them to what you offer by having them
emotionally connect with it — this is the “velcro suit effect” in reverse.
!
Nothing forges an emotional connection quite like other humans (well
ok, maybe kittens), and that’s the strategy we’re going to take: even
though your product itself clearly isn’t a person, that’s not going to
stop us from imbuing it with a personality.
Desirable or not, you already have one in all your touchpoints - even
the stuffiest, most boring content has a personality (a stuffy, boring
one!). In that sense, personality isn’t something you sprinkle onto
your experience, but instead a summary characteristic of it.
!
In order to create an effective and consistent tone across all your
touchpoints, it really helps to think of your company as an individual
person with traits, quirks, and attitudes all their own. Remember the
“I’m a Mac, and I’m a PC” ads? You want to reach that level of clarity
on your own product’s personality, then draw upon it at every
opportunity.
!
It’s the kernel that informs what to say and how to say it, when to
make light, and when to be solemnly serious. In a lot of ways, a
website is really just conversation, with one side of it pre-recorded.
Who is your audience having one with?
!
Aarron Walter, Director of UX at MailChimp, has written an entire
book on this very subject, and I highly recommend you read it (see
appendix). In it, he outlines a method for articulating all the important
parts of the product’s personality into one cohesive document he
calls a “Design Persona” — a document quite like the UX personas
that people make for their customer types, but for your own
company’s perspective, instead.
Below are the home pages for two different online form builders. Can
you imagine each of these products being actual people? Might they
even remind you of ones you already know in your personal life?

Who would you prefer spending time with on a weekly basis? Who
would you better trust to protect your sensitive information? Who
would you rather start a relationship with?
!
Note that crafting touchpoints with personality is not at all the same
as simply making it “fun” — having a wacky personality would almost
definitely not be very effective for, say, IT security software, or a
product that manages retirement funds. The point is to resonate and
connect, not to ham it up.
!
Also, don’t limit yourself to only communicating your personality via
the written word. After all, only one part of the brain speaks English,
and you want to convince the whole enchilada. Punchy colors, perky
animations, and dramatic imagery all communicate personality and
create emotional responses with the users experiencing them.
In fact, when it comes to dramatic imagery, nothing is quite as
emotionally-charged as photos of faces. Our brains are hard-wired to
recognize them: newborns have been shown to mimic facial
expressions as early as their second day alive, which means we're
picking up on facial patterns FAR before other communication
modes kick in.
!
Seeing a face immediately commands our attention & influences our
feelings. It's so powerful and so pervasive, we see faces even when
they're not really there!

Remember that American Express commercial from a while back?

Or take these two pictures of bottle openers, for instance. Spend a
moment reflecting on how drawn in you naturally become, and how
each makes you feel emotionally connected in a totally different way.

These are bottle openers, and they're making us feel something

simply because we’re recognizing a facial pattern in them. How crazy
is that?!
!
It should come as no surprise, then, to see an even greater effect
when we look at photos of, you know, actual human faces. An
activity like web browsing has us perpetually in "scan" mode, and
human faces are like magnets for that, pulling our primal attention
away from safe and boring things like text and screenshots at their
will.
It is not a power to use lightly, though. While the tactics of designing
with faces is very well documented, there's a mishap relating
specifically to onboarding that I see time and time again.
!
InVision makes excellent UX prototyping software, but their old
Customers page was a good example of what happens when you fall
into this trap:

With all the faces clustered together, your attention is constantly

pulled in an overwhelming variety of directions. It's really hard to pick
a customer to focus on, let alone pause to read the text. The
attention-stealing faces are, like the fabled crabs in a bucket, all
defeating each other.
If your site clumps faces & testimonials
together, consider how much more effective
they’d be spread out across the page rather
than stealing all the attention away from huge
blocks of non-facey content (and each other!).
They’re like gravy on a holiday feast —
unbeatable as an amplifier, but not for having
all at once on their own.
!
While you’re at it, make sure they’re not only
spread out across the page, but across your
pageS. You want faces in each step of the
journey: capturing attention, forming emotional
bonds, and propelling people along to the
next.
!
For some reason, smiling faces tend to
disappear as soon as signup happens, but
they can be just as effective for moving people
forward inside the app as out.
!
Regardless, we’re now totally prepared to
craft touchpoints that get the aforementioned
Elephant heading straight towards us. So long
as everything checks out with the Rider, we’re
golden. Let’s cover that part now!
Chapter 7
Providing Rational Ammunition

Alright! We’re finally ready to stop talking about the user and start
talking about ourselves — we’ve already captured their heart, now
we just need to get sign-off from the mind.

“People want to believe that they make

decisions rationally, logically — but in reality,
they make them emotionally first. Then they
defend those decisions with logic.”
— Tom Hopkins, sales trainer
Since we’ve already gotten the hard part of the emotional decision
squared away, all that’s left is teeing them up with the rational ammo
they need to give themselves the go-ahead for taking that first step
into the signup process.
!
The first thing we want to do is hammer home that their heart is, in
fact, in the right place and that this is exactly what they’re looking for.
To make the case, we’re going to focus on two main things: how
your product is just as good as all the other options out there, and
then the specific way that it exceeds all the other options, making it
the only logical choice.
!
These are also known as “points of parity” and “points of difference,”
and are nicely illustrated via a venn diagram model I first saw from
Chris Goward of WiderFunnel:

Points of Difference
Prospects’
Points of Parity Desires

Competitors’ Your
Features Features
Honest-to-goodness recommendation
You may have noticed that there hasn’t been a lot of talk about measuring or optimizing the
onboarding experience so far. Sadly, that’s by design — when sitting down to write this book, I
realized that covering everything about taking a data-based approach to improving your product
adoption funnel would turn this book into an unwieldy tome.

!
Instead, I recommend simply using the concepts provided in this book as a starting place for your
metrics-driven experiments, and otherwise follow the conversion rate optimization playbook that’s
already been covered so well elsewhere. If you’re looking for an outstanding book on the subject, one
of my all-time favorites is “You Should Test That!”, also by Chris Goward. I’ve even considered giving
that one out as a holiday gift to all the designers I know — total gold star material!

!
Oh, and if you’re not already tracking the key user behaviors in your onboarding workflow, there’s no
time to start quite like the present! KISSmetrics and Mixpanel both make it super easy to get started,
and your future self will thank you for having all that historical data saved up!

We’ve been holding off on discussing your product’s features since

the beginning, but you finally get to touch on them now — exciting,
no?! While you’re at it, think beyond features and even consider
listing other more general qualities of your software, like security,
speed, ease-of-use, reliability, etc.
!
Also, don’t forget to consider touching on “soft skills” like customer
service, knowledge resources, technical support, and other human
elements. If you offer a concierge setup service, for example, now is
the time to make it known loud and clear!
!
You also want to make it clear why they should believe what you say.
One great way to short-circuit any trust issues is to ask them to
instead believe what others have to say about you. Any opportunity
to include endorsements from current users or mentions in the media
should generally be jumped at.
Testimonials are particularly effective at establishing trust and
credibility, and there are four great ways to round them out when
displaying ‘em (what I call the “four horsemen of the trust-
pocalypse”):

Face

Name Title Logo

Face: As we’ve covered, they’re lightning rods for attention and add
an emotive, human-to-human punch
!
Name: Including the quoted person’s name provides a level of
authenticity that something like a Twitter handle simply can’t
!
Title: Is this person the Vice President or a parking lot attendant?
Titles help inform the reader how much authority is behind the
recommendation!
!
Logo: If the person you’re quoting is representing a super
recognizable company, including that company’s logo will provide an
excellent shortcut to credibility
Another way to approach the “establishing credibility” challenge is to
overtly walk the walk of a credible organization. If you offer things like
100% money-back guarantees, let people know! They will realize
they’re dealing with a company that takes themselves — and their
clientele — seriously. Transparency, confidence, and generosity can
go a long way.
!
Likewise, consider pursuing endorsements from well-respected
experts in the space your product serves. If you’ve won awards,
displaying them might also help in that regard (though I haven’t seen
them work quite so well, since so many of them are effectively for-
purchase).
!
Lastly, if you have the power of numbers on your side, let prospective
users know there’s safety there! Showing signs of a thriving user
base tells those on the outside that you’re onto something — where
there’s smoke, there’s fire. It’s for this same reason that restaurants
seat people at street-facing windows first: restaurants that appear
crowded are probably crowded for good reason.
!
Showing signs of hustle and bustle such as social media followers,
faves, likes and such can be helpful. However, what you really want is
to show that you’re frequented not just by lots of people, but lots of
the right people. People your prospective users identify with, and
perhaps even aspire to be.
One way to achieve this is what I call the “jeweler to the stars”
approach: openly stating that you’re in existence to serve a specific
and aspirational audience. This not only lets the “stars” know that this
is the place for them, it lets people who want to be stars know that
they should be frequenting there, as well. Framed inside that context,
abstract numbers like “follower count” become a lot more powerful.
!
Ultimately, though, what will make your user base more successful
isn’t by joining the ranks of the numerous, but by attaining the real-
world outcomes they’re looking to achieve by using your product.
After all, what’s more persuasive: “we have over 200,000 Twitter
followers,” or “our average user saves $4,985 in federal tax refunds”?

Elance’s home page is a spectacular example of both sides of this.

They start by highlighting Daniel B., who says he works “with really
talented clients” (i.e. he’s the kind of person Elance helps people
become), and then in the bottom-right, they share some very specific
and relevant vitality indicators: “114,500 jobs posted in past 30 days”
and “$984,641,452 earned through Elance to date.” Impressive!
!
It turns out that even when you’re writing about you, it’s still not really
about you! Be conspicuous in your impact, and your popularity will
follow. It doesn’t work so well the other way around (social app
products perhaps notwithstanding).
!
Anyway, we’ve already motivated and attracted the Elephant, and
we’ve now convinced the Rider. We’re WELL on our way to pulling in
super-motivated, properly-oriented prospective users. All that’s left to
do is pave that Path so nobody gets bogged down or loses their
way. Onward! Excelsior!

PRO TIP
No matter how motivated your material may help people become, there’s always a possibility that the
timing simply isn’t right. For example, if your product helps people find their dream condo, but your
visitor won’t be looking for another six months, squeezing them through the “start your trial” entryway
right off the bat won’t do either of you much good.

!
Instead, try frontloading the relationship with value by educating instead of selling. Drip email
campaigns kick total ass at this for both parties - all they have to do is supply an email address to get
some valuable information, and you get an extended opportunity to stay on their radar and build your
relationship. That way selling becomes even easier once the timing IS right. The aptly-titled product
named Drip makes these campaigns super duper simple to get started — I highly recommend them!
Chapter 8
Clearing the Runway for Takeoff

My three year old has developed a fascination

with those cars you wind up by pulling
backwards, which then speed off on their
own when you let them go. In a lot of ways,
that’s exactly what we’ve been prepping for
by ramping up the emotional motivation, and
securing the rational sign-off — a vehicle full
of potential energy, raring to be set free.

Now’s the time to let it loose and see how far it takes them. All that’s
left is to make sure they don’t hit any snags or stray off course. This
is where we curate the Path.
Fortunately, finding areas of the path that are in need of grooming is a
relatively straightforward affair, since we’re optimizing for flow. The
key is to look for the opposite of flow — halted progress. Watch
someone use your product, and note any time they have to stop
what they’re doing. Whether it’s a complete stop or even just a
momentary one, you know they’ve hit a patch that could be in need
of fixing.
!
Something on the screen caused their brain to pause to think, which
in turn caused their flow of activity to seize up. “Will I be billed when I
click this?” someone may wonder, their finger hesitatingly hovering
over a “Get Started” button. A hiccup has been introduced to the
progression of events, and it’s going to require conscious mental
effort on the user’s part to get things moving forward again.
!
We HATE those kind of hiccups because the user’s cognitive
resources (like conscious mental effort and attention) are the only
thing driving this entire experience forward, and there’s precious little
to spare, with oh so far to go.
!
Modern neuroscience has made it very clear that the brain has a
finite amount of resources at its disposal for any given task, and once
they’re depleted, they don’t come back until the brain takes a break
to recharge. Just like how our bodies can only maintain a strenuous
physical activity for so long before fatigue sets in and things start
going haywire, such is the case with our brains and concentration.
This means it’s absolutely critical to be super selective in what that
brain power is applied to. Letting it leak out on unnecessary trip-ups
or distractions really impacts how far it will take them in a single
sitting; once those cognitive resources have been used up, they’re
gone, and so is the user as they close the tab and move on to
something else.
!
That leaves us with only crossing our fingers and hoping they will
come back to try moving things further along next time, which is a
very risky proposition. Instead, we want each experience to take
them as far as possible, which means optimizing their mental load as
much as possible.
!
Remember in Gravity when things would get so tense as the space
suits were running out of oxygen, and how valuable it made every
breath become? We want to treat attention exactly the same way.
!
So let’s polish your signup touchpoints into as streamlined a first step
as possible. Just like how we didn’t want that wind-up car hitting any
snags or veering off course, there are two main problem areas we’re
going to assess the touchpoints by: ways they slow people down,
and ways they let people drift away. Or as I like to call them, Points of
Friction and Points of Disconnect.
Points of Friction occur whenever someone’s flow is interrupted,
usually by confusion or tediousness. Think of all the times you
yourself have felt all momentum grind to a halt as you squinted at a
CAPTCHA, or had to take multiple swings at guessing a site’s
requirements for a successful password. Or even real-life things like
having to leave your computer to get your wallet from the other room
because the signup required a credit card up-front.
!
That’s not to say you should never include CAPTCHAs or require
credit cards up-front — in fact, a lot of experts say that if you’re in
doubt, you should lean towards doing it (the credit card part, that is
— screw CAPTCHAs unless you’re absolutely dying from spam). The
larger point is to scrutinize everything for its propensity to be a flow
blocker, and weigh those tradeoffs very carefully.
!
Do you absolutely HAVE to get their phone number at signup? Is
knowing their business’ industry right away worth turning away a
portion of otherwise high-potential users? Is it absolutely critical to
have someone confirm their email address before they can even dip
a toe into the app? (and no, “the database requires it at signup” is
not an answer you should sleep well at night with)
Look for any and every possible way to shorten and straighten the
signup process. That means cutting out steps wherever possible, but
it can also paradoxically mean adding more at times. For example, if
you absolutely MUST get nine pieces of information in order for a
user to even see the app, consider breaking those out into multiple,
more consumable steps, rather than throwing them all up at once —
overwhelm-ment can be a snag unto itself!

1 2 3

Name

Email

Phone Next

The other side of the progress-preventing coin — Points of

Disconnect — occur whenever someone’s flow is allowed to head in
a different direction than one that progresses them through your
onboarding experience. Have you ever seen a field for a coupon
code and opened a new tab to do a search for “company X coupon
code”? That’s your flow being allowed to drift, and it’s super
dangerous, because it might not “drift back”.
Requiring email addresses to be confirmed is also a big-time flow-
drifter, since you’re actually pulling them out of your onsite workflow
and directing them straight into the nightmarish hell of distraction
known as their inbox. To avoid this, many companies allow
provisional access until it’s confirmed, just to keep you in the setup
flow as long as possible.

“Why do you need to confirm the damn email? That’s a

lot of friction. If it’s a political debate inside the company,
or a HIPPO — a Highest-Paid Person’s Opinion — that
really wants to confirm email, one trick I love is that you
let users sign up, and you just put a banner or some sort
of element at the top of the page that tells them “hey,
confirm your email” but doesn’t roadblock them from
getting through the experience.” — Hiten Shah, KISSmetrics

Email confirmation is very likely to come down as a business decision

and not simply an onboarding one. There are tradeoffs each
company will need to weigh out on its own — just make sure to
represent the onboarding perspective when they’re being weighed at
yours!
Another way flow can drift is when your site freezes up on someone.
This can often take the form of a really slow, underperforming
website, which should definitely be an area to try to improve. It can
show up more surreptitiously, though, in the form of buttons that
don’t respond to you.
!
Remember back when we were talking about websites having
personalities, and how they’re like pre-recorded conversations?
Imagine having an actual conversation with a friend — a nice,
invigorating back-and-forth affair — and you lob a question to them
like “want to grab some dinner?”, only for them to blankly stare back
at you, and stare, and stare. Kind of unnerving, right?
!
This is exactly the same as filling out a form and clicking the “submit”
button, with absolutely no sign of recognition from your website
“conversation partner.” Without that “I hear you” feedback, people
are left to turn inward: “did I do something wrong?” “should I ask
again?”
!
Set even the tiniest interactions up to be as human and responsive
as possible. You want your site to be an enthusiastic butler, not a
DMV teller reading Us Weekly behind a plexiglass window.
!
Once you’ve finished, take a step back and look at what you’ve
accomplished over the past few chapters alone: you’ve built up a
groundswell of emotion, achieved logical buy-in, and turned your
signup process into a frictionless superconductor. Nice work!
Your users have followed you each step of the way, and now have
their finger hovering over the submit button that will carry them, for
the first time ever, into your product. Once they click that button, it
will be the best chance we ever get at winning them over, and the
clock will be ticking more than ever, as well.
!
Fortunately, we’ve spent the past several chapters completely front-
loading that experience as much as possible: the mountain peak has
been charted, now it’s just a matter of scaling to lofty heights. They’re
lucky to have you on their side.
!
*CLICK*
Section 3
Helping your users achieve their
improvement

Alright! We’ve now identified the way we’re improving people, nailed
down how to communicate it to them, and made it super easy to get
started. Now we just need to actually, you know… provide that
improvement!
!
Remember back to our mountaineering metaphor, and how we put
so much groundwork in before they got started because it was going
to be such a hard climb once they took their first step? Well, we’re
there now!
They’ve taken the very first step by signing up, but just as adopting a
new set of behaviors is hard to start, it’s also hard to maintain —
!
think of all the “New Year’s resolution” gym memberships that never
even make it to February.

Well, I’m off!

?
!

Fortunately, all the orientation and motivation we’ve already provided

should be major boosters in keeping them on an upward trajectory.
Also fortunately, they still have you on their side!
!
In this last section, you will pore over all the in-app touchpoints
they’re going to encounter so you can tee them up for success at
every turn.
!
Let’s press right on!
Chapter 9
Picking Out the Quick Win

As they say, a journey of a thousand miles begins with a single step.

Likewise, getting your users all the way up that mountain is going to
require multiple experiences over time. After all, our goal is the
positive, sustainable adoption of a whole new behavior. By its very
definition, that’s going to require repeated attempts at improvement.
!
In that light, the first order of business is to take a long, hard look at
the most critical of all the attempts: the first one. We want this
experience to be extremely well-curated, because software products
across the board have absurdly high abandon rates after the first
use.
Killing Half Your Signups Before the Second Visit
Patrick McKenzie is very highly-regarded for his skills in conversion rate optimization, and has a pretty
sobering story to share.

!
“Based off my experience with [my product], I thought ‘Oh no, I’m doing something wrong — only
40% of my free trial users ever log in a second time.’ And then I got into the consulting game and
started getting to see the metrics within a lot of software companies, and they were also seeing only
40-60% would come back a second time.

!
“It got to the point where I’ve seen this across five software companies, I go into the sixth company
and ask them if they track this metric — they didn’t, because no one does — and then I said ‘Alright,
I’m going to make a prediction: it’s going to be 40-60%’ and I would usually get laughed at by the
product team, because they knew they weren’t doing that terribly.

!
“And then the numbers would come back: 43%. And you would just see the CEO, the head of
product, 15 engineers who have invested a significant portion of the last three years of their lives into
this product, and they’re just sitting around the table with their jaws hanging… I’ve never seen actual
tears when that number comes out, but you can feel that vibe in the room.

!
“So, for those of you out there, I can tell you with a fair degree of certainty that no matter how great
your product is, it is very likely that 40-60% of your free trial users never see the product a second
time. Which makes that first use of the software really really freaking important.”

Since we want those return visits like nothing else, we’re going to
stack the deck in our favor by making sure this first impression ends
with a cherry on top. There’s even science to back it up, in the form
of the psychological phenomenon called the “Peak-End rule”.
!
The Peak-End rule is a theory originally outlined in a 1993 paper, and
essentially boils down to people recalling events most strongly by
their “peak” (the most intense moment, good or bad) and their “end”
— how the experience concludes.
!
We want to use every tool at our disposal to prime for that all-
important return visit, and sticking the landing on the first visit can
only help our chances.
Going back to the mountaineering metaphor, you can almost think of
our goal for the first visit as simply getting them to reach a “base
camp” partway up: a small win that provides them with a positive
outcome to their first excursion, and one that can be used as a
springboard for future efforts.

Sure hope I can get there!

?
!

As usual, this “win” won’t be defined in terms of “learning the

interface” and instead in terms of actually helping them become
successful, even in a small way (or at least greatly increasing their
belief that the product can do so down the road).
!
You know how you can go to an ice cream parlor and they let you
sample a flavor with a tiny helping from one of those little spoons?
That’s exactly what we’re aiming for with this first experience. Simply
providing them a small taste of success now will greatly increase the
likelihood they go all-in on the triple-scoop later on.
So how do you go about determining what your own product’s first
win should be? Well, for starters, it should be something that helps
demonstrate the core essence of your product — what you lead off
with sends a very strong signal of “this is the most important way to
engage with this product”.
!
Case in point, if you’re Buffer and your first-run experience (a design
term meaning “what’s been planned out for a user’s first visit”)
doesn’t involve scheduling social media updates in one way or
another, that’s a real mismatch with your product’s core offering, and
is sending a very confusing signal.
!
Beyond that, you of course want it to be something that can
realistically be achieved in one sitting. The first-run experience for a
video hosting site like Vimeo or Wistia, for example, shouldn’t expect
people to sit idly by while their first upload takes 40 minutes to
process. Unless they direct the user’s attention elsewhere while that
chugs along in the background, that first experience is effectively
over as soon as they click the “upload” button.
It also has to be something someone is highly likely to already be
prepared to do. If you’re an email marketing product and your first-
run experience is banking on someone sending out their first
campaign right away, you better hope a large majority of your
signups are coming armed with something to say. Make sure it’s a
very safe bet that your quick win is harnessing not only a real intent,
but a current one at the moment of signup.
!
Speaking of things that might scrub the deal before it even begins,
make sure it’s also not overly dependent upon involvement from
others. If your product requires a tracking snippet to be installed and
a large portion of your user base is non-technical, this will be a
significant roadblock. Picking something else as the primary first
experience might be straying slightly from the direct activation of your
product, but it’s a whole helluva lot better than ending the first visit for
half your signups before they’ve even made it into your app.
!
Also, don’t discount the friction that comes with anything requiring
clearance. For example, if your product requires access to sensitive
data and you know that the IT team will have to sign off on it before it
can be installed, “installation” is not the way you want to lead things
off — it’s a non-starter. Instead, getting the hypothetical user to
customize and download a “get IT to approve this” kit could be the
perfect first win to log.
!
Finally, it has to be something that actually leads to engagement. I
know, this one is kinda “doye”, but it’s amazing how easy “we
want people to do this” can become a false proxy for “this is how to
make our users successful”.
!
Case in point, Twitter saw a massive spike in signup retention once
they stopped leading things off by encouraging people to search (no
one came with a search in mind) or tweet (nobody was ready to
tweet right away, either) in favor of following (everybody knew people
they were interested in).
!
Once people followed others, their timelines filled up with content
that not only demonstrated the value of Twitter, but provided new
value upon every follow-up visit. This directly led to habitual use, and
tweeting and searching followed in kind.
!
Ultimately, you want someone to walk away from their first
experience feeling a little happier, a little better off, and a little more
invested in your product than they were when they started. Score
that first win, and your life just got a whole lot easier as far as getting
them to return is concerned.
!
To boil everything down, think of it via this litmus test: what’s the one
first step in your software that, if you knew someone took it, would
make you feel WAY more comfortable in betting on them ultimately
becoming highly-engaged users?
!
Get that locked in, and then we’ll figure out the best way to get them
there!
Chapter 10
Planning the First-Run Experience

Alright! In the last chapter, we picked out the best “base camp”
endpoint that we could — now let’s plot the course for users to
actually get there!

“It’s thinking about what the customer wants to

accomplish in the first couple minutes that will prove to
them the value of the product we provide, it’s the
information that we want to know from them that will
help us serve them better, and it’s also knowing where
things are really confusing for someone using the
product for the first time.” — Jeff Vincent, Wistia
Let’s start by defining the beginning and end in terms of the user’s
improvement (as opposed to simply defining it as the steps required
for them to get there).
!
Let’s say your product is an online survey creator, and its core value
is that it gets people quick answers from a group.
!
A great first-run experience (the path that gets them to the “base
camp”), then, would be one that advances the new user all the way
to a state of kicking back and waiting for results to come streaming
in. That’d be very nicely achieved by, well, having them get a survey
out there!

End State
Beginning State

?
Taking it real easy
and just waiting for
first
Publishing their the survey results to
Just signed up survey come streaming in!

How they get there

With those two guideposts in place, let’s set about detailing all of the
steps the user has to go through to progress from one state to the
other. Let’s say our first draft looks something like this:

1. Confirm email address

2. Sign back in
3. Click “Create New Survey”
4. Name the survey
5. Fill it up with questions
6. Save the survey
7. Copy the embed code
8. Paste it on their site

Alright! So we just need to help people through all eight steps and
they’re well on their way to survey-publishing success, right? This is
exciting!
!
Hold it right there, Jack.
One of the most important things to be conscious of when planning
out user workflows is to not mistake activity for achievement (hat tip
to the late, great John Wooden for that one). Consider the contrast in
two different ways to buy something on Amazon:

Method Shopping Cart Checkout One-Click Ordering

Activity Add to cart Click the button
Review cart
Review billing & shipping
Complete purchase
Achievement Item purchased Item purchased

This isn’t to say one process is objectively better than the other —
they both have their merits — but it would be silly to say that the one
with four times the activity gets you four times the outcome.
!
And yet, as designers, it’s easy to take the steps in any workflow for
granted. Instead of taking a step back and finding the shortest path
to a real-world outcome, it’s easy to simply define progress as
“making it past the steps in our workflow,” as if the act of advancing
through an app’s setup wizard had value unto itself. This is a mistake,
because not only can steps have little correlation with actual
achievement, they can actually be preventers of it.
How? Well, no matter how helpful they are, each step in a workflow
is yet another opportunity for someone to drop off: some people will
never confirm their email address and are gone forever, and some of
those that do might never get past the following step, or the one
after that, or the one after that.
!
They will never make it to the base camp we have waiting for them,
which is a bummer for all involved. We had hot cocoa and
everything.
!
That’s not to say that having lots of steps in a workflow is always a
terrible idea — in fact, sometimes splitting one step into two or three
can make it more digestible and increase the likelihood it gets
completed. The point is simply to remember that the ultimate
purpose of a workflow isn’t to get users to complete the steps, it’s to
get them to where they want to go.
!
To take a workflow’s steps as a given is to take an activity that’s
supposed to be about a user’s progress and define it by its possible
impediments, instead — kind of backwards.
!
Let’s go back and take a really long, hard look at those eight steps
outlined a minute ago, and ask ourselves if the progress they provide
outweighs the risk they pose of letting people drop off.
 1. Confirm email address
2. Sign back in
3. Click “Create New Survey”
4. Name the survey
5. Fill it up with questions
6. Save the survey
7. Copy the embed code
8. Paste it on their site

For step 1, does confirming the email address help someone

accomplish their immediate goal of publishing a survey? Maybe sorta
— it kind of looks after their long-term interests, in case they have
trouble logging back in in the fut— you know what? Let’s cut it out,
and make that a follow-up step once they’re done publishing the
survey, instead. They’d probably be pretty motivated to do it at that
point, as well!
!
For step 2, since we’re not pulling them out of the app to confirm
their email address, we don’t need them to sign back in, so that’s
another easy one to cross off our list.
Step 3 seems like a pretty reasonable one to keep around — you
could make a good argument that we could cut out this step by
simply preloading an open “create survey” form as soon as they log
in, but there’s something to be said for training them on where to go
to create more in the future — let’s keep it for now.

1. Confirm email address

2. Sign back in
1. 3. Click “Create New Survey”
4. Name the survey
5. Fill it up with questions
6. Save the survey
7. Copy the embed code
8. Paste it on their site

Step 4 seems on the surface like a no-brainer to keep, but does a

survey absolutely HAVE to have a name? It’s really only for internal
use — specifically, once you have more than one survey and need to
tell them apart. It’s literally impossible for that to be a problem right
now, so let’s just default it to “My First Survey” and call it good. This
step goes in the waste bin with steps 1 and 2.
Step 5 is pretty crucial. I can’t even find an interesting angle on why it
might not be required. It stays.
!
Step 6 is a pretty tiny one, but even the smallest of steps should be
scrutinized. If there’s nothing happening here that an autosave
couldn’t accomplish, let’s relieve the human from having to do the
work a machine could do better. It’s also out.

1. Confirm email address

2. Sign back in
1. 3. Click “Create New Survey”
4. Name the survey
2. 5. Fill it up with questions
6. Save the survey
7. Copy the embed code
8. Paste it on their site
Steps 7 and 8 are two sides of the same coin, and are one of the
more interesting parts of the workflow to consider. They present
significant risk for blockage if the operator isn’t technical enough to
know what to do with embed code (if they even have access to their
site’s code base at all), and are a pretty complicated step outside of
the app either way.
!
If all we care about is getting them to the point where they can kick
up their heels and let the survey results roll in (and thus start
experiencing the real value of the product), we could find far-simpler
workarounds.
!
For one, there are lots of options out there for one-click installs (like a
custom WordPress plugin) that would greatly reduce the technical
knowhow requirement. Alternatively, why not make it even simpler
and just give them a link to a live page that already has the survey up
and running? They just send that to their friends or add it to a blog
post and it’s off to the races.

PRO TIP
If you’re ever in question about how positive any part of your user experience is, Temper.io is a great
way to get a “Spidey sense” for it. It’s a super simple service that asks participants to rate that part of
the experience on a “smiley, neutral, or frowny face” meter, and aggregates all the responses for you.
It’s a wonderful way to keep your fingers on the pulse without interrupting things too much!
 1. Confirm email address
2. Sign back in
1. 3. Click “Create New Survey”
4. Name the survey
2. 5. Fill it up with questions
6. Save the survey
7. Copy the embed code
8. Paste it on their site
3. Share ready-to-go link

We just shrunk a chain of dependencies down from eight to three,

and sacrificed very little power or capability in doing so. With fewer
unnecessary steps to bog them down, more people will reach the
base camp and get to drink that delicious hot cocoa. Win!

? Publishing their
survey
first

Taking it real easy

and just waiting for
the survey results to
Just signed up come streaming in!
Chapter 11
Designing for a Safe Landing

As we set out on the first leg of the journey, Let’s say someone JUST
finished signing up for your product, and we freeze time at the exact
moment before the ensuing page loads.
What do you think they will expect to see once the page’s content
pops up? In this author’s humble opinion, the smart money’s on them
thinking they’re going to see, well… the thing they just signed up for.
!
They just left the familiar territory of your marketing site to strike out
for something that they will hopefully be getting even more familiar
with very soon: your app. The sooner they return to terra firma, the
sooner they can hit the ground running.
!
However, for reasons good, bad, or otherwise, a lot of products have
users first go through a series of screens before alighting back on
stable ground. These “limbo” experiences can take many different
forms (wizards, showcases, tours, questionnaires) but almost all of
them exist to serve some combination of two purposes: to introduce
the product, and to customize the experience that ensues.
!
As far as introducing the product is concerned, you’ve hopefully, over
the course of all the chapters leading up to this one, already laid
some serious groundwork in giving people an idea of what your
product is all about. Likewise, in the coming chapters, we’re going to
cover how to make your product and interface as self-evident as
possible, so that the interface itself needs very little introduction.
For those reasons, I really recommend scrutinizing the importance of
expository content at this stage. While there’s a slim chance it will
clear up some confusion that’s slipped through the cracks, there’s a
greater chance it will just provide an annoying delay: think back to all
the times you’ve fast-forwarded your way through screen after
screen of fluffy intro copy, salivating for the chance to get started in
earnest.

PRO TIP
The exception to this rule are downloadable applications, which could have been acquired without
much or any influence from your earlier touchpoints (e.g. getting something directly from an app
store). This also goes for products where users are invited by other users. Even then, though, I’d argue
that a product capable of explaining itself is much more evocative than an introductory slideshow
could ever be.
However, the other big reason for “limbo” screens (the “customize
the ensuing experience” reason), is often totally legit. Most notably,
whenever you need information that’s critical for teeing up the first-
run experience, but isn’t likely to be changed often (or ever) after it’s
initially set in place.
!
Netflix makes heavy use of “limbo” screens en route to their
application, like this one for setting up profiles:

While cutting this step out wouldn’t have really adversely affected the
first-run experience, it’s not hard to imagine it being nice to have out
of the way, and this info certainly isn’t likely to change very often.
Netflix also uses an approach similar to Amazon’s stripped-down
checkout layout. I call it “focus mode”, because in both cases they’re
stripping out everything that draws focus away from the single task
at hand. Gone are the usual screen components such as the header,
main navigation, and more.

However, while this approach giveth, it also taketh away. For one, it
can create a bit of anxiety in its neither-here-nor-there-ness. In
Amazon’s case, it feels wholly untethered from the “real” site, almost
like a modal popup that’s just floating in space.
!
That goes double for “limbo” screens, as by their very definition the
user doesn’t even know what the “real app” is even going to look
like. This can be an unnecessary source of anxiety.
One way to mitigate that is by anchoring the limbo material on top of
the aforementioned “real” interface. Quora does this when it asks you
to start things off by picking out interests:

See how you can just barely make out the “real” site in the
background? This provides essentially the same amount of focus,
but even more orientation and motivation — you can see the cool
place you get to land as soon as you just… fill… out… this… screen.

I call this the “Emerald City in the Distance”

approach — it lets people focus on the road
directly ahead of them, while having the comfort
of never losing sight of their ultimate destination.
This keeps users grounded by immediately providing a point of
orientation inside the real app, which leads to a more cohesive, less
ambiguous experience.
!
At the end of the day, the user has taken a leap of faith by signing up.
“Limbo” steps have their place, but don’t lose sight of the fact that
the sooner you can get them back on solid ground inside your app,
the better!
!
Speaking which, what are things looking like once they land?
Chapter 12
Tailoring the First Impressions

Alright! Now it’s finally time for your product and the new user to get
acquainted. A lot of work has led up to this moment — let’s make it a
great one!
!
One trick for designing compelling and relevant interactions is to
imagine yourself standing in for the website and personally helping
the user with their improvement. How would you introduce yourself?
What are the first things you’d help them accomplish? Are there
questions you’d ask them right off the bat? What would your tone
be?
Getting a really clear idea on how you would behave in that situation
can make for a phenomenal starting place for planning out how the
website will behave. In other words, figure out the human-to-human
interaction, then design the human-to-computer one to mirror it.
When in doubt, ask yourself “what would I do if the user was
standing right in front of me rather than sitting in front of my
website?” Then design the site to replace yourself.
!
For example, one thing humans tend to do when being introduced is
greet the other person. If your app doesn’t currently welcome new
users, you might want to consider it! It doesn’t have to be anything
fancy, but a brief note of encouragement can go a surprisingly long
way. Once again, you want your site to be the world’s best butler, not
a disinterested DMV teller.

PRO TIP
Notes of encouragement also work for other key inflection points in the onboarding experience — if
someone just completed something difficult or particularly important, it doesn’t hurt to let them know
they did a good job!
However, don’t mistake a greeting for an opportunity to blab on
about yourself. Sadly, companies often think it is. Enter: coachmarks
& UI tours.

These little devils have regrettably become deeply associated with

user onboarding, to the point where many companies have come to
believe that this UI technique is onboarding. This is flat-out incorrect.
It is also, ironically, a strong indicator that the onboarding experience
was tacked on as an afterthought.
If your interface is so confusing that it needs more interface just to
introduce itself, my recommendation is to have not so confusing of
an interface to begin with. Tacking callouts on top of a poorly-
designed UI does not fix the UI, it just literally points out how poorly
designed it is.
!
On top of that, coachmarks and UI tours can actively detract from an
experience. At the very least, they’re momentum interrupters,
grinding progress to a halt until they’re either addressed, skipped, or
dismissed. Since one of our biggest goals is to clear away as many
snags from the pathway as possible, the thought of introducing more
to the mix should be met with the utmost scrutiny.
!
If you’re already using coachmarks, try this as an experiment: turn
them off, and bring in some people who’ve never used your product
before. Watch how long it takes them to figure out what the purpose
of the UI is. Note the biggest areas where they trip up.
!
Then, instead of turning coachmarks back on, fix those points of
ambiguity and confusion to make them not ambiguous and
confusing! The way to get a floundering UI to reliably stand on its
own is to strengthen its weak points, not to prop them up with lots of
little crutches.
Of course, there are certainly times when product tours have their
place. Provided they’re not being used to paper over a poorly-
conceived UI, they can be very helpful in leading people by the ear
through an introductory activity. Optimizely does this reasonably well:

Instead of having an unending blast of tooltips that basically restate

the label of the button they’re pointing to, they actively guide the new
user through performing the activity — teaching through action, not
memorization! Rather than describing what a part of the interface
does, they get the user to actively engage with it. The difference is a
powerful one.
Either way, even assuming your interface is spinning like a top,
there’s still another side to the “cold start” problem to address — it’s
pretty likely that all the content containers inside that interface still
need to be filled with stuff.

Dashboards that show app activity can be pretty depressing when

there isn’t, well… any activity yet. If these conditions are left
unaccounted for, the user is going to see a lot of zeros and “you
haven’t done X yet”-s with a weak scent of information on what to do
about it.
!
In design terms, these conditions are called “blank states” and
handling them gracefully is one of the best ways you can grease the
skids for an ultra-smooth start.
The first thing you can do is become ultra-sensitive to the tone of the
messages. Avoid saying things like “You haven’t set up any projects”
or “You don’t have any friends” — not only do these fail to assist the
user in addressing the lack of projects or friends, they can come off
sounding kind of adversarial. Especially considering that these are
often the first things a user sees upon signing up, be very careful not
to blame people for things they couldn’t have possibly done up to
that point to begin with.
!
Instead, aim to flexibly accommodate all the potential conditions —
especially the early/empty ones! — and use those as opportunities to
paint a picture of what life can be like once they’re fully up and
running.
!
For example, rather than pointing fingers and bluntly saying “You
have no friends,” use that state as a point of encouragement in and
of itself. Even something as simple as the following scores way
higher on the aforementioned “Elephant, Rider, & Path” framework:

This is where your friends will show up once

you add them. You’ll be able to see how
they’re doing at a glance and can message
them right from here — it’s pretty sweet!

Add your friends now!

A lot more helpful in resolving the “no friends” problem than simply
telling them they’re losers, right?
!
Another way some products go about populating blank states is to
just cram a bunch of fake activity and statistics into the empty areas,
with the intention of at least displaying what things would look like, if
only there were actual activity and statistics in there.
!
The fake content generated from this technique is typically called
“dummy data,” and I generally recommend thinking long and hard
before going down this road.
!
While it’s really tempting to wash away all those zeros and empty
charts with some “pretend content” that will make your beautiful
dashboard come to life, they ultimately only serve to illustrate what
your product is capable of, which should have already happened
LONG ago.
!
Don’t conflate showing someone a picture of success with actually
progressing them towards becoming more successful. Seeing a
preview of what a chart looks like when it’s filled up might help get
the point across, but it doesn’t really help someone accomplish
something. Skew towards being useful over being illustrative.
They also can get a bit in the way of people actually getting their real
data in there, by opening the door for pondering things such as “am I
supposed to do something with this, or just look at it? am I looking at
my own data, or is this fake? how do I get my real stuff in there, and
once I do, how do I know it’s my stuff that I’m looking at?”
!
Instead of injecting fake data into the blank states, consider using it
in a different part of the onboarding experience — on the marketing
site. A lot of “live dashboards” make for very compelling content out
in the wild! Baremetrics pulls this off quite nicely, and really capitalizes
on it as an opportunity for driving signups:
Another way to handle blank states that I heartily do recommend is
what I call the “content-as-tutorial” approach. It’s actually quite
similar to the “dummy data” approach, but with one crucial
difference: the content doesn’t exist merely to be seen, but to
actively instruct.
!
Basecamp does an absolutely phenomenal job of this.

They not only set each new Basecamp subscription up with its own
preloaded project, but the topic of the project is “Explore
Basecamp!” — they use the product’s content to explain how the
product works!
Once you’ve clicked in, you can see it even goes a level deeper —
the project’s own content is self-referential, and each piece actively
guides you through using its own little corner of the interface.

The “content-as-tutorial”
approach kind of reminds me
of the Voyager golden record
— that sample of Earth’s
audio that got blasted into
space back in the 70s.

Since the people behind the project wisely accounted for the
possibility that alien life forms might not have the same hi-fi
equipment we do, they printed a non-verbal set of instructions on the
back of the record, to help whoever found it figure out how it could
be played.
!
And that’s really the central notion of what we’ve been exploring this
chapter — first creating an experience that needs as little explanation
as possible, then making the remaining explanation a core part of the
product itself.
!
Now that we’ve gotten things started off on the right foot, though,
how do we ensure one step leads to another?
Chapter 13
Driving to Victory

While nailing the first impression gave us a big leg up on kicking

things off right, we’re going to need to sustain that advantage if we
want to get as many people as possible to that “base camp”
success state. Let’s turn our positive introduction into some serious
momentum!
!
Using a product for the first time is remarkably like entering into a
real-life situation for the first time. Once you’ve gotten your initial
bearings (see last chapter), you start casing the joint for indications
on how you’re expected to act.
Social environments (and the people that make them social) tend to
give you a pretty quick idea of what sort of behavior they encourage.
For example, you’d need mere seconds to realize that you’re
expected to behave very differently in a church in Omaha versus a
subway train in Tokyo versus a night club in Miami.
!
Likewise, we want to position the interface to tee its new users up
with all the “behavioral handholds” they need to feel confident
moving forward, and continuing to do so. On that note, one of the
strongest behavioral cues going is what other people are doing.
!
There’s a famous (and pretty amusing) clip from Candid Camera
where a mark would be standing alone in an elevator and actors
would trickle in all around him. Instead of facing the door like normal
people, though, the actors would all face one of the walls. Sure
enough, the original person (the non-actor) would turn to face the
wall, as well! Social pressure can be pretty compelling!
To that end, it seems a bit odd that all kinds of interpersonal
motivators — smiling faces, social proof, etc. — that are so effective
in driving engagement in the marketing materials outside the product
suddenly disappear once you’re inside it.
!
Just as you would look to the behavior of your fellow Nebraskan
churchgoers or Japanese subway riders as a yardstick for your own
actions, surfacing social proof within the product can be a very
helpful signpost for which activities are highly encouraged.
!
There’s no one-size-fits-all recommendation for approaching this, but
leaderboards illustrate the concept very nicely. When you call out
particular users for their performance, you’re holding them up as role
models and establishing what “good” looks like. In that sense, you’re
not simply showing who’s achieved the most, but which
achievements are most valued to begin with.
!
Just like how cooking show hosts will often reveal a finished dish
long before the one they started is done baking (“here’s one I
prepared earlier!”), so too can you hold up a successful user as an
example of what a new user could become once they’re up to
speed.

RED ALERT!!
This chapter is going to bump up against some very gamification-y approaches, but don’t take them
as an endorsement of gamification as a pursuit unto itself. People don't like feeling manipulated, and
using tricks to advance people through an irrelevant funnel isn't nearly as sustainable a strategy as
making that funnel actually relevant. People will always be more motivated to improve their real selves
than to gain virtual badges, and removing “artificial sweeteners” from your experience only helps to
clarify what’s working for you and what isn’t.
Of course, there are going to be lots of products where showing one
user what another user is up to would be a huge no-no (like, of the
you-get-sued-into-bankruptcy variety), but there’s still one type of
person you can always include as a guide: you!
!
GetResponse does this really well, offering human help in multiple
prominent places right on their app’s welcome dashboard. The offers
even feature faces of real people, just like what works a landing page!
Of course, being on hand to help pays off in more ways than simply
providing an assist to each individual that pipes up. Otherwise, that’d
be a pretty unsustainable customer acquisition strategy for all but the
biggest enterprise customers.
!
The real value of maintaining a presence inside your product lies in
keeping a very close read on the pulse of how it’s experienced. This
lets you not only identify problem areas, but also understand their
nature on an intimate level. This way, you can fix the rough patches
for everyone - one-on-one for the person who piped up, then at
scale for all the others who didn’t!
!
Intercom has built an entire product around this concept, and is one
of the finest ways to target, segment, and communicate with your in-
app users. If you’re looking to initiate and facilitate conversations with
your current user base — which I highly recommend you do! — I’m
not aware of a better product to get you there.
!
Would you like to hear a perfect story that illustrates how keeping the
communication lines open provides a feedback loop for greatly
improving the product? Sorry, I wish I had a good one but I don’t…
Just kidding, I totally do.

Perfect story I actually have for illustrating the concept

Dan Martell is a tech investor and founder of Clarity.fm. Before Clarity, he founded another company
named Timely. Timely’s onboarding process primarily involved going through the signup workflow and
then scheduling a tweet to go out at a later time. Curiously, Dan found that a lot of people were
getting right up to that last part — even going so far as to connect their Twitter account — but
stopping short of actually scheduling the tweet.

!
He reached out to many of the users who never got around to the tweeting part and quickly found out
that while people really liked the idea, they often didn’t have anything to say at the very moment they
were signing up.

!
Since depending on people coming back to finish things later on is a very shaky proposition —
especially after their first visit didn’t end in a small win — Dan looked to find a way to serve them up
with something to say right there in the moment. He brainstormed for a bit on the most universally
tweetable content, and hit on something that scored big: famous quotations.

!
After adding a “suggested quotes” feature, he saw his activation rate (the percentage of users making
it to Timely’s “base camp” of tweet-scheduling) rise from 7% to 70%. Being helpful can really pay off!

However, if leaving people completely out of your product is more

your style, there’s one other well-established technique for keeping
people on-track and motivated: send them on a series of quests! *
!
Human brains hate leaving things unfinished and, conversely, love
achieving goals. Once someone accepts a task, it places a
reservation in their head that will nag at their conscious mind until
they’ve cleared it away by completing it. And once they do, they get
a nice endorphin rush and a feeling of accomplishment.

* “Quests” might be a bit grandiose, but it’s a lot more fun to call them that rather than “tasks”
If you take a big goal (whatever the “base camp” win is) and chop it
up into smaller, more immediately-achievable tasks, you lay out a
series of “impulse buys” that many people will find very hard to resist.
After completing one trivial step after another, they suddenly find
themselves fully up and running.
!
Like the “displaying guidance from others” approach, this also takes
the onus off the user in figuring out what they should be doing in
order to explore the product’s core activities — you’re literally telling
them “these are the most important things to do right now.”
!
From a UI perspective, this is typically accomplished with something
that resembles either a to-do list or a completion meter (aka progress
bar). What they look like isn’t really the important part, though — it’s
what they do: get more people to complete the task at hand by
explicitly stating the steps a user needs to take, and reporting on
their progress as they go.
Note that these are quite different from wizards & tours, which
constrain a user’s focus and abilities to a spotlight section within the
app (a modal popup, for example). Setup quests are actually the
opposite, in that they encourage exploration in the product, and
(mostly) self-directed accomplishments. If wizards are like soapboxes
for the product to stand up and introduce itself, these are more like
scavenger hunts.

Quora does a pretty phenomenal job with their setup quests,

especially in one regard: notice in the screenshot how the “Set Up
Your Feed” list has three of its five items checked off? It’s interesting,
because this is the very first screen a user sees when they’re
dropped into the app from the signup modals.
That is to say, this is really a two-item list with three things added
onto it that you couldn’t have NOT already done. Which is to say
they’re making heavy use of something called the “endowed
progress effect”, which is a psychological phenomenon that basically
boils down to this: the closer people think they are to completing
something, the more likely they are to actually see it through.
!
There was a famous experiment conducted at a car wash, involving
those “buy X and get one free” loyalty punch cards. They gave half
the customers a ten-wash card with two “starter punches” and gave
the other half an eight-wash card with no punches, then checked
back later on to see at what rate the two groups filled their cards up
with punches.

Phil’s Car Wash Phil’s Car Wash

2 3 4 5 6 7 8
1 1 2 3 4 5 6 7 8 9 10

It turned out that the first group got their free wash at almost twice
the rate of the second, even though both groups needed the same
exact amount of punches to get there.
!
Why? Well, when you have two punches out of ten, you perceive
yourself as already being 20% of the way to completion, while the
no-punch group was starting out at 0%.
In the same exact way, Quora took a two-step activity with 0%
progress and turned it into a 60% progress five-step activity, instantly
transforming what could have been “you need to do these two
things” into “you’re practically done already!”
!
When people perceive themselves being that close, it’s practically
irresistible to not go all the way. And when they do, please, for the
sake of all that’s good and decent, congratulate them for it! It is
absolutely mind-boggling to me that sites have setup processes that,
when completed, simply disappear without even acknowledging that
they were successfully achieved.
!
Your user and you (in the form of your website) just won something
akin to a three-legged race. Be with them in that moment!
!
A criminally-undervalued aspect of product design is the act of
simply acknowledging that someone has achieved something
important or complex (or both). Their brain, knowing it just did
something good, is flooding with positive chemicals — be the thing
that it bonds with in that moment, not a stone wall it has to work
around.
!
Positive encouragement costs you absolutely nothing to implement
and can provide outsized effects on emotional adoption. Plus,
remember the Peak-End rule from Chapter 9? We want to make sure
people know darn well how swimmingly things wound up!
Also, a post-success message is the perfect time to slip in a few
additional recommendations, a la “while we have this good thing
going, how about uploading a profile picture?” It very well may find
them in a receptive mood.
!
And if not, that’s no big deal. We got them to the base camp, and
they will always be able to come back to the “quick win foothold”
they established on their first visit. There will be plenty more
opportunities to keep driving them up the mountain. In fact, that’s the
very subject of the next chapter.
!
In the meantime, though, take a second to pat yourself on the back:
you — and your users — have come a long way!
!
!
(See what I did there?)
Chapter 14
Creating “Regulars”

Ok, ok, that’s enough celebrating for now. It’s really great that your
onboarding experience is primed for getting as many people as
possible to that super-important quick win, but this is no time to bust
out the touchdown dance. Sadly, one positive experience does not a
thriving user make. That takes time, and lots of repeat visits.
!
The real value of your product lies in the sustained improvement of
the person using it, which is going to require a full adoption of the
behavior change we initiated way back in the “pain of switching”
chapter.
It’s like we’ve set them up with a phenomenal first workout at our
gym, and now it’s our job to make sure they keep coming back so
they can finally attain that beach bod they’ve always wanted. No
“New Year’s resolution” flunkies allowed!
!
In that way, you will almost be acting like their personal trainer —
totally invested in their improvement, and working to make sure
they’re totally invested in it, as well. Engineering a way to simply get
people showing up over and over will eventually fail if people aren’t
seeing results. The visits have to be meaningful ones, centered
around accomplishment.
!
So how do we re-engage in a way that improves? Fortunately, I
happen to have a couple ideas on just that subject!
!
One thing that really drives people to see things through is social
accountability. To extend the gym membership metaphor to perhaps
its breaking point, think about how often you hear people say that
not wanting to let their “gym buddy” down was the only reason they
went to work out instead of hitting the snooze button that morning?
!
The more you can get people to connect with others inside your app,
the stronger their commitment becomes. For social apps whose
value explicitly IS connecting with others, nailing the “naturalization”
process is of course a no-brainer. That said, it can also help products
of all stripes.
Think about how much public
reputation is a driver for
contributions to sites like
Stack Overflow or Wikipedia.

Or how anonymized conversations help drive transactions at sites

like AirBnB and CraigsList.

Or how posting one’s

listening history keeps
people playing music
on Rdio…
… or how announcing a completed run keeps people logging them
in RunKeeper…

… or how sharing important

Dropbox folders with others
makes the prospect of
changing synching services
a daunting one.

Humans are social creatures. When they extend their social

behaviors and interactions through a product, their bond with that
product (and the people with whom it connects them) becomes so
much stronger.
!
One might think that B2B products would be excluded from this, but
I’d actually argue that an even stronger case can be made for them
over their consumer-centered counterparts.
Businesses are made up of people too, and while a great many
consumer products are made for individuals, B2B products are
almost always designed for the benefit of entire teams (directly or
indirectly).
!
While it may initially be more challenging to get a whole team up and
running as compared to a single user, that “gym buddy” effect
becomes a compound effect as more and more people are added.
Products like Basecamp and HipChat, for example, become
significantly more useful (and thus more indispensable) once the initial
user has gotten all the other players involved.
!
That “initial user” is often called the “internal champion,” and helping
them find success in getting everyone up and running can be an
absolutely crucial element of B2B software adoption. Remember,
you’re there to help your users accomplish all their related goals —
on the screen and in the office alike. An assist to any part of the
adoption process lifts all ships, including your own.
!
And just as you want to be comprehensive in helping their initial
needs, you also want to assist them as things change over time.
Enter: lifecycle emails.
The primary function of lifecycle emails is to do something your site
can’t: go get your users where they are and pull them back into your
app. That’s to say, if your gym members aren’t showing up, lifecycle
emails drive out to their house and haul them out of bed on your
behalf.
!
That said, the end goal of lifecycle emails is to eventually not need
them, in the same way that you don’t permanently install training
wheels — the point is to help see the adjustment period through,
then let the “real” use take over. For software, that means habitual &
unprompted use.
!
To accomplish this, lifecycle emails should be set up to nudge people
along through the most critical inflection points of the journey from
signup to thriving user. They’re kind of like a joint between two
bones, in that sense: acting as the connective tissue that links one
key activity to the next.
!
For example, one of the most well-established lifecycle messages out
there is the “welcome” email. This is triggered when someone
completes the signup process (though many companies delay its
delivery a bit), and tries to get people to reach out for help should
they need it.
They can range from a “personal welcome” from the CEO to an
accounts person letting you know they’re always around to help if
you get stuck, but the end action is almost always the same: getting
the user to initiate a conversation.
!
If we were making a “Mt. Rushmore” of lifecycle messages, the
“you’re making progress — congrats!” email would also be a shoo-in.
This one is triggered by a user event (closing their first sale, perhaps),
and serves as a catalyst for some sort of follow-up activity that builds
on their positive momentum.
!
An interesting variation of the “you’re making progress” email is when
it’s triggered by something someone other than the user themselves
did. Medium’s “your post is on the move” and LinkedIn’s “someone
endorsed you” emails are both stand-out examples of positive
encouragement that was initiated by someone else’s activity.
!
Lifecycle emails can also be triggered when events don’t take place.
For example, another absolutely classic lifecycle message type is that
of the “hey, come back!” variety. This happens when the user hasn’t
been active in the application for a particular amount of time. The
event that it drives is, of course, a return visit — the more specific
and goal-oriented, the better.
Finally, taking the “Abraham Lincoln” spot up on Lifecycle Mt.
Rushmore, we have the “you’re running out of time!” message type.
These are typically set to pop slightly before a trial period is going to
end, and attempt to play on people’s sensitivities regarding loss-
aversion and urgency in order to get their action initiated (that action
usually being to start paying for the product).
!
These can often come off as a bit desperate, especially if it’s one of
the first times you’re getting any email from that company at all.
Likewise, if the other three emails are doing their jobs (especially the
first two), then this one won’t be super necessary.
!
And that’s kind of the beautiful thing about this whole process we’ve
set up, from the very beginning of chapter one until now — every
piece of legwork sets a stronger stage for success, and eases the
burden on the ones that follow.
!
Hoping that a “your trial’s expiring” email will spike sales among
people who've never even finished their setup process is doomed
from the start. For a robust, high-vitality user, though, it’s a pleasant
reminder of how far they’ve come. If all went well, cementing your
relationship isn’t even a decision for them at that point — it’s simply a
reflex of realizing the enormous value you’re providing.
Mutually-beneficial, self-sustaining engagement has been Plan A
from jump street, and nailing all the steps along the way should have
you both sitting very pretty right now. You have created a machine
that cranks out fireball-throwing Super Marios, in all their kick-ass
glory. And best of all, you get to share in their success.

So there you are, you and your user, together at the top of the
mountain. Take a moment to appreciate how far you’ve both
ascended — the view up there is pretty fantastic, isn’t it?
Further Reading (and Watching)
Want to take things even further? Check out these books & videos!
As always, these aren’t affiliate links; just honest recommendations
for things that have made me better at what I do.

Kathy Sierra’s talk at Business of

Software 2009
If I could get every web/product designer in the
world to watch a single hour-long presentation,
this is the one I’d choose (in a heartbeat).

http://businessofsoftware.org/2010/05/
kathy-sierra-at-business-of-software-2009/

Integrating Around the Job to Be Done

Clayton Christensen’s 16-page report from 2010 has influenced
my thinking about delivering value more than just about anything
else over the last few years. Highest recommendation!

http://hbr.org/product/integrating-around-the-job-to-be-done-
module-note/an/611004-PDF-ENG

Likewise, check out lots more of the #JTBD

framework over at jtbd.org!
The Secrets to Driving Massive
User Growth
Josh Elman took 30 minutes to drop serious
knowledge about how he helped fix onboarding for
LinkedIn and Twitter, to an amazing effect.

https://www.youtube.com/watch?
v=AaMqCWOfA1o

You Should Test That!

Chris Goward, of WiderFunnel, wrote what I consider the best
book on conversion rate optimization available today. If you’d
like to get better at a data-driven approach to design, this is the
book for you.

http://www.youshouldtestthat.com/

Scientific Advertising
On that note, Claude C. Hopkins penned an amazing piece
on the subject way back in 1923. 1923! It also goes much
deeper than simply regarding advertising — read it for ways
to communicate value in any form. Also, it’s in the public
domain so you can find it for free very easily.

http://en.wikipedia.org/wiki/Scientific_Advertising
Designing for Emotion
Aarron Walter’s contribution to the A Book Apart
catalog is not only one of my favorites in there, it
also touches on a really underrepresented subject.

http://www.abookapart.com/products/
designing-for-emotion

Extra Credits
This is a web series about video game design, but there is a LOT that can be applied directly to any
interactive medium. A LOT. In fact, it’s hard to even narrow down the videos I recommend starting with.
Starting Off Right, Tutorials 101, Achievements, The Skinner Box, and Gamification are all super great
and very directly related to onboarding.

https://www.youtube.com/user/ExtraCreditz

Your Brain at Work

If you’re at all interested in understanding your brain in order to become
more productive, David Rock’s book is an absolute killer. Much more science
than self-help, it’s great for helping with designing for other people’s brains,
as well!

http://www.your-brain-at-work.com/
 Don’t Make Me Think
If you ask 10 designers where they first discovered the
importance of usability, there’s a very good chance all of them
will say it was Steve Krug’s seminal and eminently readable
book from 2005. Still wonderful & relevant today!

http://www.sensible.com/dmmt.html

MicroConf Presentations
MicroConf is a yearly software conference, and in 2012 both Patrick McKenzie and Dan Martell put on
presentations that were absolutely outstanding and provided amazingly actionable onboarding tips.

http://www.microconf.com/videos-2012.html

and also see http://training.kalzumeus.com and http://clarity.fm

The Lean Series

Eric Ries teamed up with O’Reilly Media to create a
wonderful series of books covering key lean concepts in
more detail. Croll & Yoskovitz’ Lean Analytics and Laura
Klein’s UX for Lean Startups are both phenomenal.

http://theleanstartup.com/the-lean-series