You bust your hump to create a category-defining product with hockey-stick growth, you constantly roll out new features, throw piles of cash toward Facebook ads, and work overtime to get people to sign up for said product.

And then what happens?

~~~ Whoosh ~~~

What’s that sucking sound?

It’s the sound of signups leaving your product. Tons of them. Never to be seen or heard from again.

If you’re like virtually any software company out there today, roughly half your signups never come back a second time.

And if you’re ALSO like virtually any software company out there today, the vast majority of your signups never, ever make their way to becoming anything even resembling full-fledged users.

This sucks. (get it?)

But really, it does — it sucks users out of your conversion funnel, which means in order to grow, you have to replenish it with new signups at a more and more feverish rate.

It also sucks for the people signing up — no one wants to waste their time checking something out and have nothing but abandonment to show for it.

And lastly, it sucks for you. You just aren’t getting a full return on the sweat equity you’re pouring into your product.

Sure, you can overhaul your onboarding experience to address the problem, but — hang on, let me put my mind-reader hat on…

… I am sensing that all your designers and engineers are already busy cranking out new features and squashing preexisting bugs, and that it would take a moonshot to land your current roadmap on time, let alone to do so with an overhaul added to it.

Is that roughly correct?

If so, I feel your pain.

I myself have directly experienced that pain with every onboarding redesign I’ve ever worked on, as well as literally every client I’ve ever consulted with.

The problem is universal; you will simply have to make peace with your leaky funnel, and your signups will simply have to content themselves with mediocrity.

There’s just nothing else to be done about it.

Unless… there IS something to be done about it.

Your Signups Deserve Better

What if there was a way to invest in a super effective lever for engagement and retention WITHOUT having to take your product team’s focus away from what they’re already committed to?

What if you could reliably guide your users to the promised land, not just hurriedly in the first few minutes of signing up, but comprehensively and over the first several months of using the product?

And what if it required effectively zero engineering and design time?

I’m not talking about stapling one of those janky tooltip tours on top of your not-so-user-friendly interface (because we both know those just don’t work).

I’m talking about TRANSCENDING your interface entirely.

Friend, I’m talking about lifecycle emails.

“Lifecycle emails” is the catch-all term for all the messages you send someone after they sign up for your product, preferably prompting them to take meaningful actions that improve their lives in a significant way.

• Want to welcome them and thank them for joining?
  That’s a lifecycle email.
• Want to introduce them to a feature they haven’t tried yet?
  Totally a lifecycle email.
• Want to tell them they haven’t logged in for a while and you miss them?
  That’s one of the less-effective examples, but an example nonetheless.

Lifecycle emails are great for a number of reasons, the biggest of which being that you’re reaching out to users who aren’t currently in your product and pulling them back in, guiding them to value.

Making changes to your in-product onboarding can’t do that, because, well… they’re only seen by people who are already in your product.

People hoped their lives would improve with your product in it — that’s why they signed up, right? — but if only a sliver of them actually get to experience that “good life”, then that’s a wasted opportunity for both them and you.

Lifecycle emails act like guardrails for their motivation, keeping signups chugging along on the path to success you offer (and becoming exactly the awesome, churn-proof users you’re working so hard to get).

Still, company after company after company that I encounter treats lifecycle emails as a total afterthought, rather than a source of high-ROI opportunity.

In fact, there’s a very good chance that your own approach is — hang on, let me put my mind-reader hat back on again…

… I am sensing that you’re sending out a few scattershot post-signup messages delivered via some unholy mix of 3rd party products ranging from marketing to billing to transactional emails, all of which create an analytical black box that makes it impossible to track their performance or iterate over time, much less do fancy things like split testing.

Also, most of the emails have inconsistent branding, look weird on mobile phones, and sport copy that was never designed to actually convert users because it was written by an engineering intern while they were fixing a bug a couple years ago.

Oh, and there’s also a decent probability that there are a couple other messages being sent out that YOU DON’T EVEN KNOW EXIST.

Is that ALSO roughly correct?

If so, once again, you’re far from alone.

So far from alone, in fact, that I’ve decided to personally step into the ring and do something about it.

After years of preaching the gospel of lifecycle email optimization and still seeing so many companies underuse them to such a significant degree, I have had enough.

I will just do the damn thing for you.

In other words…

[Liam Neeson voice] I have a very particular set of skills. Skills I have acquired over a very long career. Skills that make me a nightmare for… all the reasons your signups are abandoning your software even when they shouldn’t be.

Skills like:

• Finding the highest-ROI user actions in your product
• Prompting those actions with timely messages
• Sending emails that people actually enjoy getting
• Optimizing subject lines until the cows come home
• Winning back “stale” users with resurrection messaging
• And, like, so much more… A. WHOLE. LOT. MORE.

If you want to do all of these on your own, that’s awesome. I’m highly confident you will find a lot of success with them.

But if you would like some help…

[Liam Neeson voice again] I will do all of the above for you, I will find tons of ways to improve your processes, and I WILL kill… a significant amount of your churn rate.

“How do I sign up?”

Easy. To make sure we’re a great fit, please simply take this super-quick survey and then buckle up for the ride of your life.

(Seriously, it’s just 5 questions, one of which is “what’s your email address?”)

I’m really excited to work with you.

Here’s to super-boosting your onboarding together!

Don’t let fragile user onboarding ruin your UX

In 2006, I made a big decision: I resolved to throw everything I had into pursuing a career in software design.

I’d been handcrafting GeoCities-like websites for myself and others since the late ’90s, but now I wanted to get serious about it.

I hit the books hard and was fortunate enough to almost immediately come across Bulletproof Web Design by Dan Cederholm.

The book covered techniques for crafting sites in such a way that they could be viewed across a wide variety of conditions — different browsers, different screen sizes, etc. — without flying apart at the seams and looking completely broken.

That concept might sound super obvious now, but I am embarrassed to say that at the time, it blew my freaking mind.

When I’d learned to create websites in the ’90s, there was an ideological war going on that often involved bragging about a website being “best viewed” in one browser or another, effectively telling everyone else to take a hike.

But in reading Dan’s book, I realized that there was, of course, no “right” way to view a website, and that if we as website creators wanted our creations to succeed, we needed to accommodate all the ways in which they were experienced.

Instead of prescribing a single “right” way and accepting the fragility that comes with that specificity, it’s far better to aim for something so robust that it can take any weird thing you throw at it.

The lesson, in short, was that when you address uncertainty with flexibility, you generate resilience.

And this, dear friends, is a quality I often find sorely lacking in many onboarding experiences.

Just as there isn’t one “right” browser to use, there also isn’t one “correct” way to start using software. People arrive at a product with all kinds of different intentions, perspectives, and levels of familiarity.

We can either meet that uncertainty with something hyper-specific, superficial, and brittle, or we can welcome it with a flexible and resilient experience that serves users of all stripes, ambitions, and timelines.

It’s all a matter of thoughtfully considering and applying the most “bulletproof” options available for our onboarding experiences.

By way of example, consider…

A (very) fragile onboarding pattern

Let’s talk about tooltip tours! You know, these fun little homies:

They seem pretty helpful on the surface, right?

Perhaps your product has a few key activities that the interface doesn’t make super apparent on its own, so you tack a handful of callouts on top of it, ensuring that the important parts get noticed. Isn’t that a good thing?

It might seem so at first blush, but think about the times you’ve experienced these in the wild as a user: How “helpful” did you find them?

Chances are much more likely that you found them:

• Distracting, like when a tour pops up when you’ve just gotten ready to dive into something — or worse, when you’re already in the middle of it
• Controlling, like when it takes over the entire screen and makes you click next-next-next-next until it finally puts you back in the driver’s seat
• Flaky, like the times when you accidentally get kicked out of a tour before it’s over and can’t start it again to see what you missed

“Distracting, controlling, and flaky” is a description befitting a horrible ex or the reviled Clippy, not a quality onboarding experience.

Each of those qualities also make the getting-started process remarkably and profoundly fragile. In other words, the opposite of bulletproof.

In the ultra-important first few moments a user spends within a product, we want to set the bar much higher. In fact, we should shoot for the exact opposite of each attribute:

• Instead of distracting, let’s aim for integrated
• Instead of controlling, let’s aim for empowering
• And instead of flaky, let’s aim for steadfast

Together, they combine like Voltron into…

The Holy Trinity of onboarding bulletproof-ness

1. Integrated (as opposed to distracting)

When it comes to your onboarding experience (or any product experience, really), one of your very best friends is your users’ sense of immersion, momentum, and flow. You want your users to form a bond with your product, and getting them into an immediate groove is an excellent way to do just that.

Techniques like tooltip tours, intro videos, and even those little pulsing hotspots, however, hijack your users’ attention and pull it away from their natural sense of self-direction. This not only throws cold water on their overall momentum, it also disengages them from the meaningful activity they would otherwise be immersed in.

Whenever possible, the absolute ideal is to instead make your product’s onboarding experience completely indistinguishable from the product itself. Instead of slapping an “interface on top of your interface,” find ways to integrate timely, relevant guidance within it.

As a user, things are simply much more meaningful when it feels like you’re the one calling the shots.

2. Empowering (as opposed to controlling)

Speaking of “meaningful,” is your onboarding experience guiding users into actions that genuinely lead to progress in their lives, or just a better understanding of your UI? People act when they believe that doing so is aligned with their ambitions, and very few people wake up in the morning aspiring to become better “interface operators.”

Pay particularly close attention to those times when tooltips and coach marks call out individual buttons, especially when it creates a redundancy like “Clicking ‘Create Project’ creates a project!” If your onboarding is simply reiterating what the interface should already make clear, that’s an excellent sign that you instead need to rework things on a fundamental level — callouts like those often literally point to bad design.

People are signing up for your product because they hope it will make their lives better in some way. Guide them to that promised land (more on that in a bit), rather than taking them on a tour of UI whack-a-mole.

Users can accomplish meaningful things in your app — highlight those, not your interface’s shortcomings.

3. Steadfast (as opposed to flaky)

If your onboarding only extends as far as the first minute or two a user spends in your app, it’s not only competing with other information that users have to wrap their head around, it’s also abandoning them before they’re fully up and running (which can easily take days, if not weeks).

Even when a user is fully up and running, it still doesn’t mean your onboarding’s job is done. What a user finds irrelevant now could very easily wind up being highly relevant to them down the road, especially when you consider the fact that your product will also be evolving during that time — “new feature onboarding” is also very much a part of onboarding!

Just as you don’t stop being a parent once your kids are grown, providing some timely guidance at every stage of the relationship easily beats stuffing everything into a fleeting “you better hope you remember all of this when you actually care about it down the road” onboarding memory test.

Invest in the long haul, and you will find your efforts more than rewarded.

With these onboarding bulletproof-ness concepts in place, let’s investigate how they can be applied via…

Some far-less-fragile onboarding patterns

Empty states

Your product is a place of activity, and if no activity has yet taken place, it’s going to have some empty containers reflecting that.

Many products miss a giant opportunity by simply reporting “there’s nothing to see here.” Or worse, some even provide an admonishing “you haven’t done anything yet” condemnation.

You can do much better, by providing some context around why it’s worthwhile to do the things that fill the container to begin with, and teeing people up with a call to action that gets them on their way.

• Are they integrated? Empty states are the very definition of integrated — they’re literally part of your product whether you design for them or not, so you might as well make them effective!
• Are they empowering? They definitely can be! It depends on how thoughtfully you reframe the “you don’t have anything” message into a call to action that guides people toward doing something of consequence.
• Are they steadfast? You better believe it, baby! Unlike, say, an intro tour, these puppies stick around until the user has actually done something to address them, which means they provide help on the user’s schedule.

Progression systems

Taking your users from “completely new” to “fully capable” is a journey — and one that can be rather lengthy at times. Progression systems are super helpful for guiding users along each stage of that journey.

They often take the form of to-do lists (with items that get crossed off as the user completes them), or completion meters (like LinkedIn’s infamous “thermometer of agony” profile strength meter), or some combination thereof.

Regardless of how they’re displayed, the key part is to highlight the most important activities inside the app — and, of course, to demonstrate the progress users are making as they complete those activities!

• Are they integrated? While they may not be a completely natural part of the app, they’re also far from distracting or interruptive of the organic flow within a product. Think of them as providing a great fallback option for the user, rather than an element that’s competing for their immediate attention.
• Are they empowering? As with the empty states above, any onboarding experience is only as empowering as you choose to make it. That said, progression systems are among the patterns most closely aligned with spurring users to do things of actual consequence, which is what the concept of empowerment is all about.
• Are they steadfast? Yes, totally! They’re specifically designed to work over the long haul (think in terms of multiple visits, not just the first). Pro tip: If someone reaches 100% progress, you can always graduate them to Level 2 and start them off on a new series of quests!

Lifecycle emails

This is the catch-all term for all the messages you send someone after they sign up. Ideally, the emails are dynamically based on a user’s activity (or lack thereof) within the product, rather than a cookie-cutter series of info blasts that go out to everyone, regardless of their level of progress.

When someone signs up for a product, they’re doing so because they’re motivated to find a better way of doing things. That’s unlikely to fully happen in the very first visit, so I like to think of lifecycle emails as guardrails for that motivation.

Lifecycle emails (and their sister pattern, push notifications) are unique in the onboarding world, as they’re the only patterns that actively go out and bring people back into your app — hopefully in a way that motivates them to take meaningful action.

• Are they integrated? They aren’t part of the product at all, so it’s hard to say that they’re “integrated” per se. Then again, they do absolutely nothing to distract from the task at hand once a user arrives in the product.
• Are they empowering? Ideally, yes! Nagging emails like “You haven’t logged in for two weeks — we miss you!!” aren’t particularly empowering, but ones that outline a key action for a user to take (and sell them on why it’s to their benefit to take it) definitely are. As with anything, it’s all about proper framing.
• Are they steadfast? When done well, they absolutely are! Too many software companies underinvest in lifecycle emails, meekly sending a couple when someone signs up and then calling it a day. If what you’re sending your user base is genuinely helpful and relevant, you should have no hesitation in loading up — think dozens, not a couple, and months-worth, not days.

Onboarding will always be as unique to a particular product as that product is to the world, and there are tons of other patterns to explore for your own onboarding.

Hopefully, however, this framework provides you with the principles by which to evaluate them.

People ask me all the time to name one or two onboarding design patterns that I like, but nothing in design (or life, for that matter) is ever that universal.

The honest answer is that there simply is no silver bullet.

Fortunately, though, you can always strive for bulletproof.

Bulletproof User Onboarding was originally published in UX of User Onboarding on Medium, where people are continuing the conversation by highlighting and responding to this story.

Yes, there is! Ever feel like your hard-earned signups aren’t sticking around as long as they could be? Or that your onboarding experience isn’t quite right, but you’re just not sure how to improve it?

This workshop is designed to make you SUPER smart with all of that.

“And you’re teaching it?”

Yep, this is put on by yours truly, Samuel Hulick, the person behind UserOnboard and the teardowns you (probably?) know and love.

This workshop boils down everything I know into a collaborative, hands-on afternoon of onboarding amazingness.

“This workshop is hands-on? How so?”

It’s been designed from the ground up with a single goal in mind: for you to leave feeling like a magical onboarding wizard, brimming with proven ideas to put into place as soon as you’re back in the office.

You can expect some high-level guidance for big-picture thinking, but mostly lots of tactics and exercises we do together during the workshop, as well as a personalized roadmap for applying it all afterward.

Your friends and colleagues will be like “wow there’s a new sheriff in town.”

(The “sheriff” is you, and the “town” is kicking ass at keeping more of your product’s signups.)

“Sounds good! What, specifically, will I learn?”

The lessons and activities go way, way beyond just the first use of your product (though that’s also very important!), and cover all the highest-leverage ways to retain and grow your user base.

Just some of the silver bullets I’ve collected over the years include:

• How to identify the areas where you’re losing the most users (and what to do to stop losing them)
• How to home in on the core value your product delivers like a heat-seeking missile
• How to not only set your users up for immediate success, but keep them coming back for more
• How to leverage customer support, marketing, product, UX and more to have everything pulling in the same direction

“Wow, that sounds like a lot!”

Gosh, there’s seriously even so much more. You will have to join to find out, though!

“Ok, how do I join?”

Glad you asked. It all comes together on Friday, May 19th.

The workshop runs for four hours, starting at 1pm (CEST). It will be held at a to-be-announced location close to the center of beautiful Amsterdam:

Krom Boomssloot 22-III, 1011 GW Amsterdam, Netherlands

Tickets are $1,995, and the workshop is designed to deliver a 10x ROI for you, at a minimum.

“What do I have to do to prepare?”

You don’t have to do a thing! Just come ready to have your mind exploded.

That said, your ticket does also come with an immediate download of the Complete User Onboarding Package, which includes a LOT of material to help you out between now and the day of the workshop.

You can read/listen/watch as much or as little of it as you’d like beforehand, though — it’s just that exploring more ahead of time will just help you become smarter faster.

“Do you have a return policy?”

Tickets are transferable, but non-refundable. That means that once it’s bought, it’s bought, but you can hand it off (or even sell it, actually) to anyone else.

This is to help everything go as smoothly as possible and to provide as much quality time with each attendee as possible.

“How do I know if it’s right for me?”

If you care about more people successfully adopting your software into their lives (and it sticking there), this is for you.

You can be anywhere from an early-stage startup to a billion dollar unicorn and still get a ton out of it either way. If you’re pre-product, though, this is not for you.

The roles that are most closely tied to user onboarding are usually:

• UX Design
• Product Management
• Do-It-All Founders
• Marketers
• Customer Success/Support-ers
• Engineers

And if your job title actually has the term “User Onboarding” in it, I will personally give you a hug. (only if you’d like. no pressure)

“Will there be snacks?”

Oh hell yes there will be.

Also drinks. And breaks. And really nice gift bags. This is not my first rodeo.

“I have some other questions not answered here…”

Questions are wonderful! Please don’t hesitate to reach out to me at samuel@useronboard.com, with any little thing.

That’s my personal address and I respond to everything I receive there. I absolutely love hearing from anyone who cares about user onboarding. Fire away!

“Actually I’m ready to buy now, but hate scrolling.”

You know I got you covered, boo:

(p.s. the probability of this selling out quickly is quite real; workshop sizes are limited so you can get intimate, custom-tailored advice)

An elementary school teacher of mine once assigned us an exercise that seemed simple on the surface, but turned out to be surprisingly complex.

It also wound up informing my entire philosophy on creating software.

The assignment’s simple-seeming description was this: “Write out each of the steps involved in making a peanut butter & jelly sandwich.”

However, its hidden complexity was hinted at with the following warning: “And make sure you write down every… single… step.”

I went home and thought about everything that went into making a PB&J sandwich, and wrote out each of the steps as clearly as I possibly could.

The day the assignment was due, we all walked into class to see an ominous pile of sandwich ingredients and utensils laid out on her desk.

She then pointed around the room and had each of us, one by one, stand up and read out loud each of the directions we’d written down.

And for each step we provided, she would advance her sandwich-making task with a punishingly literal — and, for a bunch of 4th-graders, hysterical — accuracy:

• If the first step was to “get out two slices of bread”, she would tear the bag open from the middle, since she hadn’t been instructed to first undo the twist tie at the end.
• Or, if another step was to “put jelly on one slice and peanut butter on the other”, she would simply place each jar on top of its own slice of bread.
• Or, if we remembered to include “scoop the jelly out of the jar with a knife” but forgot to include opening the jar itself beforehand, she would stab at it with the knife until our shrieks of laughter intervened.

And on and on it went, each student’s set of directions succumbing to one omitted instruction or another, each sandwich winding up a total mess — if it was even completed at all.

Our instructions created crappy sandwiches because they failed to bridge the gap between what seemed obvious to us and what actually happened in reality.

Whereas our first set of instructions might have looked something like this…

… there were ALL KINDS of things happening in between those steps that we failed to account for:

That’s a lot to leave out!

And while kids messing up sandwich instructions by not “minding the gaps” in between isn’t a really big deal, when we in the software world have users systematically slipping through the cracks of the products we design, it definitely is.

When someone signs up for a product, they’re expressing a sense of hope — a hope that their life will be improved with that particular product in it.

When a product fails to guide its users to the “better life” that they’re hoping for, those users stop using that product. When this happens at scale, it is (ahem) bad for business.

For this reason, the more comprehensively we can bridge that gap in between — the fewer “holes” we have in our “PB&J recipe” — the more everyone benefits.

Which is why, as a designer, I am CONSTANTLY asking myself this one simple question:

Every single time someone uses software, they’re aiming to be transported from the situation they’re currently in (and don’t want to be in anymore) to a situation that they’d rather be in.

Figuring out what has to happen in getting them from one situation to the other is our principal job.

For example…

• If someone is swiping around on Tinder, what happens in between that and them being on a date?
• If someone has an entrepreneurial dream and is thinking about using Kickstarter to turn it into a reality, what happens in between that and them having a fully-funded project?
• If someone’s simply browsing for movies on Netflix, what happens in between that and them watching one?

Regardless of whether the switching of situations is pretty straightforward (finding and watching a movie) or super complex (starting a new career), there are nearly infinite ways that we can work to ensure that our users successfully make it from one side to the other, so long as we “mind the gap” closely enough.

You can think of it like bridging a literal divide: the more comprehensively we provide assistance in making it across, the more people will survive the journey (and continue being users of our product).

Each step of that journey represents an opportunity: either an opportunity to leave it up to the user to figure things out on their own (which risks losing them), or an opportunity for us to be helpful (which builds loyalty and earns their ongoing engagement).

The “help” we offer can come in many forms. The software and its manifold features are one of them, but so are knowledge centers, blogs, podcasts, webinars, workshops, books, in-person training, video courses, and so on.

In fact, there are so many ways to be helpful that most companies have no problem coming up with areas to invest their time and energy. Instead, the problem lies in figuring out which areas are highest-leverage.

So how DO we get a read for where the best “get them from one situation to another” opportunities lie?

It involves a process that, fortunately, is as straightforward as it is effective: a little process I like to call “Break It, Break It Down.”

Here’s the playbook:

1. Pick two points of progress in someone’s life
2. Break down what happens “in between”
3. Repeat steps 1 & 2 for the gaps between each of those points

Let’s work through an example together, shall we?

I mentioned Tinder earlier, so let’s run with that:

1. Pick two points of progress in someone’s life

When kicking this exercise off, I always like to start with situations that are as “software-agnostic” as possible. This helps avoid mistaking the software we already happen to have in place with the actual progress they’re looking to achieve.

Pro tip: for those playing along at home, a great starting place is to think about a situation someone may have been in right before they pulled up your product, and what they may then go on to do immediately upon leaving it.

In Tinder’s case, the “before” and “after” scenarios are pretty straightforward. Some users may be aiming for a long-term relationship, while others may be shooting for something less involved (ahem, booty call), so let’s land somewhere in the middle and just call it “seeking out a date”:

This might seem like a pretty rudimentary “gap” to cover, but trust me — there’s a universe of opportunity to explore here.

On to step 2!

2. Break down what happens “in between”

For the first round of breaking things down, it’s ok to be pretty “high-level” — the point isn’t to be comprehensively granular (the rest of the exercise should take care of that), it’s just to get a general lay of the land.

For the purposes of this exercise in particular, let’s just make some educated guesses. The high-level “instructional PB&J” version of the dating process probably looks something like this:

For now, the important part is that it tees us up to explore what happens in between each of our “educated guesses” on the progress curve, which brings us to…

3. Repeat steps 1 & 2 for the gaps between each of THOSE points

And heeeeeere’s where it really gets interesting, because exploring the “(stuff happens in between)” for each of THESE steps can produce a whole lot of gems.

Here’s the first of the new, mini-gaps:

What has to happen between wanting to be on a date and putting yourself out there?

In a digital environment like Tinder, TONS:

That’s quite a lot — and that’s just the first gap!

If any of these mini-gaps have their own “incomplete bridges” that people fall through, the consequences could be dire: after all, if you don’t complete your profile, it’s highly unlikely you will find a match, and if you don’t find a match, you definitely won’t be going on a date!

This is why —

Hang on, I really need to emphasize this…

In order to earn your users’ ongoing engagement, it is absolutely crucial to attend to each and every one of their steps toward success, especially in the early going.

In fact, you can even break down the steps in between the IN-BETWEEN steps(!!). For example, what has to happen between “writing about yourself” and “sharing photos showing what you look like”?

Well, before you can share the photos, you have to upload them. And before you can upload them, you need to pick them out. And before you pick them out, you have to possess them in the first place.

As designers, we have a choice with each and every one of the tiny steps above: we can either stick the user with “go scrounge up whatever you have, and figure out what to do with it,” or we can instead invest in helping them have a kick-ass set of selfies that show off their best side and pull in romantic interest like a goddamned lightning rod.

It doesn’t have to be a crazy-intense effort like sending a professional photographer to take glamour shots of every new signup (though AirBnB famously achieved great results with something rather similar). It’s just that if you’re looking for inspiration for features or marketing opportunities, this is where the soil is particularly fertile.

And again, this is just one tiny, tiny leap in a series of — when you chart it all out — thousands. When you really dive into breaking it all down, it can begin to feel like this at times:

Which might seem intimidating, but you can actually look at it as exactly the opposite: as design god Charles Eames was known to say…

“The details are not the details; they make the design.”

… and this approach can take away a significant amount of the guesswork regarding which particular details are most worthy of your attention.

If you leave too many “gaps” in areas of progress in your users’ lives, you will find something else leaving: your users. This is especially true early on, when a new signup’s cost of switching is itchy-trigger-finger light.

For that reason, it is crucial to know which details to focus on and which ones to skip — if enough of your users go away, so does your business.

Anytime we decide to skip out on attending to a particular step (or mini-step, or even mini-mini-step), we are effectively saying “we will stick the user with figuring this one out on their own”:

• Want to go on a date but don’t know what to wear?
  “User figures it out” will never beat a Tinder guide to savvy dressing
• Want to start a project but don’t know how to attract donors?
  “User figures it out” will never beat a Kickstarter ‘find your friends’ button
• Want to watch a movie but don’t know what’s good right now?
  “User figures it out” will never beat a Netflix recommendations algorithm

“User figures it out” is always a losing strategy when it comes to key steps in the progress curve, because it means that instead of providing assistance, we’re leaving people with one of these:

What specifically makes it a losing strategy is that there are three very likely ways in which users will then #DealWithIt:

1. Go somewhere else to figure it out, and then come back once they have
2. Go somewhere else, get distracted, and wind up not coming back
3. Decide not to #DealWithIt at all and leave the app for good

All three are sub-optimal options on our end. When they come back in scenario 1, they’re probably a little fried from the context-switching. And in scenarios 2 and 3, losing them is literally what is happening, by definition.

If we want to earn their ongoing engagement and retention, we need to take the cognitive load of “figuring things out” off their plates whenever possible.

It may sound like coddling, but they’re just one person with a very full day, and your app is, especially at first, an incomprehensibly small part of their overall lives.

However, on the other side of the equation, you’re a whole team!

Of professional software designers!

Who think about your product all day long!

Counting on your *users* to care more about your product than *you* do results in the erosion of both.

If you can’t be bothered to invest your time in facilitating progress in any given step, why on earth should they?

In order to hit the retention metrics necessary for scaling and sustaining your business, it is imperative that you smooth your users’ path forward at every opportunity.

Fortunately, however, that doesn’t mean creating a tedious interstitial stage for each step. In fact, it’s actually best when it’s just the opposite: rather than provide a plodding, Playskool-level “My First Interface” for your users, instead harness the power of technology to warp your users right past the tedium of having to deal with the task at hand at all.

Want a real-world example? Look no further than Medium.com (aka “where you are right now”).

Ever wanted to tweet a highlight of a compelling passage that you just read?

They COULD have gone the “#DealWithIt” route and left it up to the you, which would involve the clunky, user-has-to-leave-the-product workflow of:

• Highlight the compelling passage
• Take a screenshot
• Locate the screenshot
• Upload it to Twitter
• Come back and copy the post’s url
• Go BACK to Twitter and paste THAT
• Look things over before pressing “Tweet”
• And then, finally, remember to come back to Medium to pick up reading wherever you’d left off

Instead, Medium warps you through ALL OF THAT by providing this helpful little Twitter icon whenever you highlight something (whoa, this is about to get meta):

When you click on it, you’re teed up to tweet it out from the article itself!

And then you’re free to keep reading, having never even left your place.

If you’d like to try it out on your own, here’s a big, fat opportunity to share that baller design quote from earlier (it’s a real crowd-pleaser):

“The details are not the details; they make the design.” — Charles Eames

Either way, the important point to appreciate is that Medium attends to this particular workflow’s otherwise-tedious steps by auto-magically transporting you right past them.

This is good for you because it cuts out a bunch of steps you don’t actually care about, but it’s even better for Medium because they’ve prevented the risk of you leaving and possibly not coming back!

That’s quite an amazing way to be helpful, isn’t it?

And really, “being helpful” is the ultimate expression of this approach.

Remember when I said there was one simple question I asked? Well, that was kind of a lie. There are two questions.

I don’t JUST ask myself “What happens in between?”…

I actually ask myself:

Because whether we’re crafting elementary school sandwiches, or romantic intrigue, or new business projects, or movie-watching experiences, people are only as invested in something as they stand to benefit from it.

And serving that need benefits us, in return: nothing earns ongoing engagement (and the ultra-valuable retention numbers that come with it) quite like comprehensively bridging the space between “where people currently are” and “where they want to be”.

In that way, it’s often our best shot at getting to where WE want to be.

So long, that is, as we don’t forget to mind those gaps in between.

I tweet good things at @SamuelHulick and @UserOnboard.

When I was a kid, I saw an episode of Full House that in a small, weird way, helped make me the designer I am today.

The episode involved D.J. going to middle school for the first time. She was immediately shocked and embarrassed by how her new schoolmates looked so much more “adult” than she did.

She was also dressed in the same outfit as the lunch hall monitor, which is, you know… brutal.

So the next morning, she decided to try wearing a TON of makeup to school. This resulted in her sister essentially calling her a juvenile sex worker and her father telling her that she couldn’t leave the house.

[ Note: This is not an endorsement of the identity politics in the Full House universe. The point is simply that she didn’t get her desired outcome. ]

Things looked bleak until Aunt(?) Becky swooped in like a fairy godmother and dropped some serious cosmetics knowledge on her head, teaching her that…

“… the secret to wearing makeup is to make it look like you’re not wearing any.”

She went on to explain that the point is to “bring out your natural beauty,” not to draw attention to the makeup itself.

Software is like makeup in that way: you only notice it when it’s messed up.

As a designer, I find it odd that once a product team has noticed that the interface is messing up, there seems to be a very strong tendency (especially during user onboarding) to then add even MORE “makeup” on top:

Doing that is the “D.J.” response, not the “Becky” one.

“More interface” does not fix “bad interface”… it amplifies it.

Think of the times you’ve encountered someone sporting a bad combover or a prolific amount of tanning spray (or, ahem, both): not only is it not fooling anyone, it’s actually highlighting the thing it’s intended to conceal, while hinting that something questionable lies beneath.

Like walking into a bathroom that has a conspicuously generous mist of air freshener hanging in the ether, doubling down on a messed-up UI only leads its recipients to think “HOLY SMOKES do I probably want to avoid intimate contact with whatever that’s covering up.”

It’s a problem that is making itself more pronounced, rather than acting as a magical magnifier of natural beauty.

“Ok,” I hear you say, “but what if our product doesn’t HAVE natural beauty? What do we do then, hot shot?!”

The good news is that the fundamental nature of any interface, unlike a regular face, can be changed!

You are only as stuck with your current UI as you choose to be.

Whenever you’re tempted to layer more interface on top of a problem you’ve found, that’s a clear opportunity to rework what’s already there instead.

Strive to create a system in which the good thing for your users to do is the obvious thing for them to do, without additional instruction or distraction.

Don’t be like Deej, highlighting a problem by trying to disguise it.

Navigate your product to its own place of natural, intuitive service first, then amplify THAT instead.

With a well-formed foundation in place, you may even find that you don’t need any “cosmetics” at all.

I reside in Portland, OR, which means I live in the Pacific Time Zone.

However, I don’t really “live” on Pacific Time Zone hours. The hours I keep are more like someone from Tokyo.

In fact, no matter where on Earth I live, the hours I keep are more like someone on the opposite side of wherever that place is on the globe.

This is because I have a sleep disorder that shifts my sleep/wake cycle to a pattern that’s roughly the exact opposite of a normal 9–5 schedule.

Most people’s bodies regulate their biological clocks using melatonin: it makes them drowsy at sundown and alert at sunup. For whatever reason, though, my body seems to have the opposite response.

The short version is that I get super tired when the sun comes up, and then when it goes down again I perk right back up for the rest of the night.

I am, in a biological sense, nocturnal.

It’s somewhat like Delayed Sleep Phase Disorder, which Wikipedia describes as the following:

“… a chronic dysregulation of a person’s circadian rhythm (biological clock), compared to the general population and relative to societal norms. The disorder affects the timing of sleep, peak period of alertness, the core body temperature rhythm, and hormonal and other daily cycles.”

The only difference is that instead of my sleep schedule being “delayed” by a few hours, I’m shifted fully opposite: day for me is night, night for me is day.

The upshot is that it is very weird and, in many ways, completely sucks.

One of the ways in which it sucks comes from how misunderstood it is.

I myself didn’t even understand it for a ridiculously long time.

As a young adult, I was constantly regarded as lazy or unserious about any 9–5 job I had, which was completely reasonable because I was regularly showing up late, unshowered, and totally groggy.

The reason I was showing up like that, though, was because I was regularly staring at the clock unable to sleep all night, until finally succumbing by sheer force of will around 6 or 7am, then promptly sleeping through my alarm an hour later, only to eventually wake up on a couple hours’ sleep, have my heart race when I saw I was already supposed to be at work, and throw on clothes while trying to pat down my bedhead as I ran out the door

The act of going to bed each night was extremely stressful because it meant playing Russian roulette with my employment every following morning: I had no idea when I would be able to fall asleep, so I had no idea when I would wake up, and I had no idea why it was happening.

I tried a million different things: no caffeine, no bright screens, taking sleep medications, keeping curtains closed, reading boring books, and nothing worked — not reliably anyway, and if you can’t count on it, that really doesn’t solve the Russian roulette problem.

It was also hard in a social sense, because even when people pretty close to me (co-workers, friends, etc.) would sympathize, I could tell deep down they still didn’t really think it was a “real” thing, like I just wasn’t disciplined enough. It led to so much well-meaning-but-still-misplaced empathy from others over the years:

“Yeah, sometimes it’s hard for me to make myself drag myself out of bed too.”

“Man, I totally remember staying up until, like, 4 in the morning every so often when I was in college.”

“Oh yeah, if I have caffeine after the sun sets, it takes me hours to wind down — have you perhaps tried cutting that out?”

It wasn’t until I started having live-in relationships that, by sharing a bed (or most nights, not), anyone other than myself finally caught on to just how legitimate of a condition it is.

It’s not that I’m undisciplined or that I have poor sleep hygiene or that I even have trouble sleeping at all; if I went to bed when my body is naturally tired and woke up when it’s naturally awake, I’d be among the most regular people you know in the sleep department.

“Insomnia” is the inability to either stay asleep or fall asleep, but both of those are totally fine for me — it’s just that they have to happen during the daytime in order to be so.

In other words, I could easily keep a 9–5 schedule, so long as it was one that went from 9pm to 5am.

On that note, the other reason it sucks is because I have rarely been able to experience anything resembling that ever-so-elusive regular sleep schedule.

It would be one thing to lean into my nocturnalism and not have to fight my natural rhythm on a constant basis, but that would also mean sacrificing a ton of civilian activities that everyone else probably takes for granted.

It would have been profoundly difficult to find a decent job, for one thing. Graveyard shifts at factories, nighttime security patrol, and stocking shelves at 24-hour grocery stores aren’t exactly the entry points to lucrative or fulfilling career paths.

I’m beyond fortunate to have my own design consultancy and can therefore make my own hours to a very significant degree, but even in our high-tech, asynchronous age, clients reasonably enough need to meet at least every so often. That usually involves me wrenching my sleep schedule forward or backward by twelve or more hours, and therefore losing a half a day of anything even resembling rested productivity in the process.

And if I want to involve myself in other normal daily activities like going to the bank or the post office, or picking up dry cleaning, or, say… parenting, then that also means I need to stretch my sleep schedule one way or another to make room for them whenever they arise.

Imagine a parent-teacher conference casually being scheduled for midnight, or a work meeting where the only time that’s good for everyone else is 3am, or your friends and colleagues inviting you out to “happy hour” at 6am.

Now imagine this all day, every day, with everything you’re surrounded by and everyone you care about. It feels very much like pulling a “graveyard shift” a few times a week (or more) just to participate in normal life. For that reason, I’m also extremely selective in which activities I commit to.

Even with relatively few daytime things on my calendar, the wrenching back and forth involved also produces compensatory ripple effects in order to make up that missing sleep in the days that follow, which means it’s exceptionally rare that I know exactly when I will be awake or not more than a few days out in general.

In short, instead of keeping a regular sleep schedule during the daytime, my current approach to establishing a “daily rhythm” is to essentially not have one at all.

This is why it tends to be very difficult to book anything more than a couple days out, especially when it’s accommodating something like a 9–5 EST business day: 5pm Eastern is 2pm Pacific, and 2pm Pacific is basically 2am for me. There’s a chance I might be up: it’s possible I will still be awake at 9am after pulling an all-nighter in order to make an 8am daytime commitment that morning, or it’s possible that at 1pm I will be just waking up to prep for a 2pm client meeting that afternoon, but otherwise, I will probably be asleep. Because, again, it’s “2am” for me.

This is also why I’m probably way less disposed to schedule a time to “just jump on the phone for a few minutes” than other professionals are; I totally get that a 10 minute phone call is a very small commitment if it’s in the flow of a normal day, but it is a WAY bigger commitment if that 10 minutes involves contorting my entire sleep schedule just to accommodate it.

I often really wish I had a more “normal” sleep/wake schedule, and definitely wish it was at least more predictable.

Still, it is what it is and I’m doing my best to make the best of it, in a world whose day feels like night for me.

If you’re reading this because I’m sending it to you in response to a schedule request, I hope it adds some clarity to the conversation.

If not, I’m pretty much always free around 10pm Pacific time, if that happens to be a convenient time for you to have a quick chat about it.

Day for Night was originally published in Interconnections on Medium, where people are continuing the conversation by highlighting and responding to this story.

*pause*

Ok let’s do this.

I’m a UX designer, and I find a lot of satisfaction in my work because it’s all about making software better at helping people improve their lives.

And, I like to think, it plays a small part in making the world better itself.

A couple years ago, I made a graphic to encapsulate my philosophy:

It has since been a joy to help some amazing companies turn more of their users into the “fireball-throwing” versions of themselves, to everyone’s mutual benefit.

That work has also led to lots of travel all around the world.

And, while I was away on one such trip recently, my wife went out on a date with someone else.

When she told me it happened, I wasn’t angry or hurt or jealous, largely because I knew about it ahead of time, and also because I suggested she do it, and also because the person she went out with is our girlfriend.

My wife and I are polyamorous, which in essence means that we encourage each other to cultivate multiple simultaneous loving relationships.

In simpler terms, it means that we date other people outside our marriage, and sometimes do so together.

We find it rewarding because we see affection as an inherently good thing, and think the world could use more of it in general, and find that sharing it doesn’t diminish what we have for each other, but actually enhances it.

We also find it rewarding because we see supporting each other in “exploring everything the world has to offer” as part of how we help each other become the “fireball-throwing” versions of ourselves.

It’s also, well… pretty hot at times.

If you’re curious about polyamory unto itself, this is an excellent overview:

The short version of the above is that monogamy is the only relationship model that our society currently endorses, and “polyamory” is often used interchangeably with “non-monogamy” as dual umbrella terms for the wide (WIDE) array of relationship models that fall outside of that.

A few years into our marriage, we didn’t find monogamy to be working for us, so we began to explore and experiment with alternative approaches.

It was far from easy at first. Many fuck-ups were made, most of them mine. At times it was brutally painful. And even now it still requires plenty of effort, respect, and communication (lots and lots and lots of communication), but we’ve successfully managed to navigate our relationship to a trusting, supportive, and rock-solid place that we wouldn’t trade for the world.

I can see how it definitely isn’t for everyone. But, with divorce and infidelity rates as high as they are, monogamy clearly isn’t for everyone, either.

I generally question the value in holding up a single relationship model as “the only good one”, and wonder if it leads us to impose upon ourselves an unnecessarily narrow paint-by-numbers approach to romantic morality and, in so doing, also impose it upon those we love.

On a societal level, when that paint-by-numbers prescription leaves people on the margins because they find themselves capable of loving multiple people at once, or loving someone of their own gender, or questioning their gender to begin with, I take serious issue with it.

I take serious issue because people should never be punished for conducting themselves authentically and loving others consensually: it isn’t that those who do “fail” to fit into society; it’s that society fails to include them.

We appear to be heading into a very dangerous time to be a marginalized citizen. It feels as though the world is splitting itself open in all directions, with those on its perimeter about to bear the brunt of its turmoil.

We, now more than ever, have an opportunity and an imperative to side with the vulnerable and to normalize diversity in whatever capacity we can.

So, today, I’m not only allying with people who have alternative approaches to love and sexuality, I am coming out as one of them.

To whatever extent I belong, I will proudly stand with any group of individuals who have the bravery to examine the authenticity of their identity, and the courage to live it.

When the definition of what’s considered “normal” becomes narrower and the stakes of being outside it become higher, openly “being yourself” becomes an act of resistance.

It is a visible and ongoing vote for broadening the parameters of our culture’s attitude toward involvement and legitimacy.

I understand that sharing this will probably affect my career, and that it will leave at least some people thinking that I’m perverted, or sick, or sad. I get where that’s coming from; I’m embarrassed to say that there was a time when I thought all kinds of people with marginalized identities were perverted, or sick, or sad, as well.

What ultimately changed my thinking was simply being around a more diverse array of people and seeing them as, strangely enough, people: individuals with hopes and dreams and challenges and nightmares, who conduct their lives without wanting to take away from anyone else, and who, like all of us, are simply trying to make it through this confounding world in one piece and, just possibly, while we’re at it, get to watch some Game of Thrones and keep up with whatever Beyoncé’s doing.

It is astounding how much more alike we all are than we give ourselves credit for, and it is tragic how viciously we reject that tiny percentage of difference, rather than celebrate it.

But the times, as they say, are a-changing. And at a dizzying clip.

The internet truly is disrupting the world, in both the “Silicon Valley” sense of entrepreneurial opportunity as well as the “full-scale global unrest” one.

It is up to us to determine whether that disruption leads to either our unburdening or our undoing.

I cast my faith in the former. It may be naive, but it sure as shit beats the alternative.

I cast my faith in the power of 7 billion souls all waking up to each other, and the normalization we experience when we share ourselves openly and see that there is such a prolific variety of “others like us” that we can only eventually conclude that, indeed, we all are “like us”.

When we see more and more people as normal, our definition of “normal” itself broadens, and our understanding of the human condition increases, and we as individuals grow in return.

When we love each other, we act as lights in the darkness for one another. And by that light, we learn more about both the world and ourselves.

So here is me, offering whatever light I am, with whatever light I can.

“We must,” as the poet W. H. Auden wrote on the eve of World War II, “love one another or die.”

Love isn’t disgusting. Not when it’s practiced consensually and honestly and with integrity of spirit.

Our collective sense of connection is even, perhaps, what makes us human to begin with.

Or, at least, what makes being human worthwhile.

We are all in this together, or not at all.

We truly are no strangers — none of us . And, especially now, cannot afford to be.

If this resonates, please share it widely. It isn’t my own echo chamber that I’m trying to reach.

If you have any questions about polyamory, you can email me at samuel@useronboard.com. I’m by no means an expert on the topic, but I’ve put a lot into understanding this over the years and will give you the best of whatever I have.

Also, if your company creates software designed to support minorities or diversity efforts of any kind and you’d like some UX help, holla at me at the same address and we can figure something out.

Be helpful. Fuck haters. Throw fireballs.

— Samuel

The seatback in front of me had an interactive screen set to “flight tracker” mode, aka the “watch a tiny icon of your airplane fly across a globe, Indiana Jones style” view.

One of these kind of things:

Except I wasn’t flying from Hawaii to San Francisco (this is just a photo I found on the internet), I was flying from Portland to Amsterdam.

There were a few things I learned by watching the map as I Indiana-Jonesed my way across it:

1. Holy smokes, Greenland is HUGE

2. Iceland is the first country that feels like “we’re finally on the other side of the Atlantic”

3. And we were about to fly over some islands I’d never noticed before

They had interesting names, like Tórshavn and Klaksvik and Sandavágur. Which country did they belong to, though?

They were closest to Scotland, but the names definitely didn’t sound Scottish. The next-closest country was Iceland, but that was a bit of a stretch, distance-wise.

What was going on here? Was this an entire country I’d never heard of?

It turns out it sort of was!

It’s an archipelago called the Faroe Islands which, according to Wikipedia, are an “autonomous country within the Kingdom of Denmark.”

A quick Google Image Search revealed that the island landscapes are simply bonkers:

… and…

… I mean…

… they’re like an Escher drawing come to life.

So who on earth lives there? And what do they do?

By heritage, Faroe Islanders are a mix of Norse Vikings and Scotch-Irish seafarers who have lived a highly isolated existence dating back well over a thousand years.

They have their own language, their own government, and of course their own traditions. They operate independently from Denmark with all their local affairs. Their primary industries are fishing and sheep-herding.

Searching YouTube turned up a multi-part documentary delving further into their lives.

Here’s one such shepherd, Johannes Paterson:

He lives in this farmhouse, built over 1,000 years ago:

He is the 17th(!) generation of Patersons to live and work inside it.

Here’s his wife, Guórió (prounounced Goori), pot-boiling some whale blubber for their family:

The Faroe Islands have a controversial relationship with whales, for two primary reasons.

One, they harvest pilot whales in a yearly event called a Grind (rhymes with “thinned”) that has caught scorn from the international community for perpetuating a tradition that slaughters a threatened species.

Two, that same international community has polluted the surrounding oceans to such an extent that the mercury levels in the whale meat are effectively poisonous. The local government has strongly recommended that pregnant women and children avoid eating it entirely.

Guórió is pregnant with their third child, but eats whale blubber anyway, because that was what she was raised on and that is what she knows.

And so, through a few moments of curiosity, I suddenly found myself aware of a mercury molecule inside the blood of a baby, inside a woman inside a house built before the printing press was invented, inside an island inside an independent nation I had never heard of but was flying over, and all of this because I noticed some odd letters on the screen in front of me.

How many wonders do we fly over every day? How many worlds within worlds does our universe contain, so long as we take the time to see them?

Reality is such a trip. Zoom in as high or low as you like, and there is always something fascinating to marvel at. It’s like Charles & Ray Eames’ profound and moving Powers of 10…

… or exploring the Mandelbrot Set…

… except for everything.

Infinite terrain. Infinite opportunities, so long as we control our awareness, so long as we work to develop it like a muscle.

It is, in many ways, the most human thing we can do.

This superpower we all have was so well captured in this passage by Kurt Vonnegut [gently edited for ease of reading]:

At ten o’clock, the old writer announced it was his bedtime. There was one last thing he wanted to say to us, to his family. Like a magician seeking a volunteer from the audience, he asked someone to stand beside him and do what he said. I held up my hand. “Me, please, me,” I said.

The crowd fell quiet as I took my place to his right.

“The Universe has expanded so enormously,” he said, “that light is no longer fast enough to make any trips worth taking in even the most unreasonable lengths of time. Once the fastest thing possible, they say, light now belongs in the graveyard of history, like the Pony Express.

“I now ask this human being brave enough to stand next to me to pick two twinkling points of obsolete light in the sky above us. It doesn’t matter what they are, except that they must twinkle. If they don’t twinkle, they are either planets or satellites. Tonight we are not interested in planets or satellites.”

I picked two points of light maybe ten feet apart. One was Polaris. I have no idea what the other one was.

“Do they twinkle?” he said.

“Yes they do,” I said.

“Promise?” he said.

“Cross my heart,” I said.

“Excellent!” he said. “Now then: Whatever heavenly bodies those two glints represent, it is certain that the Universe has become so rarefied that for light to go from one to the other would take thousands or millions of years. But I now ask you to look precisely at one, and then precisely at the other.”

“OK,” I said, “I did it.”

“It took a second, do you think?” he said.

“No more,” I said.

“Even if you’d taken an hour,” he said, “something would have passed between where those two heavenly bodies used to be, at, conservatively speaking, a million times the speed of light.”

“What was it?” I said.

“Your awareness,” he said. “That is a new quality in the universe, which exists only because there are human beings. Physicists must from now on, when pondering the secrets of the cosmos, factor in not only energy and matter and time, but something very new and beautiful, which is human awareness.”

He paused.

This was his finale: “I have thought of a better word than awareness,” he said. “Let us call it soul.”

Yes, let’s!

Terra Infinitum was originally published in Interconnections on Medium, where people are continuing the conversation by highlighting and responding to this story.

Unless your product is eyebrow-raisingly basic, there’s a very, very good chance that a new user won’t get to experience all the value you have to offer in their very first sitting.

And since user onboarding isn’t merely the process of introducing your new signups to your product’s features, but instead the process of driving people to success, getting there will take many follow-up trips.

For that, you need to think of ways to get people logging back in — something your interface can’t do on its own because, well . . . the user would already be there!

Instead, you need a system for continually going out to where your users are and luring them back to the good stuff. And for that, there’s no place better to find them than their inbox.

Enter: lifecycle emails.

Lifecycle emails 101

Not sure what the term “lifecycle email” means? Don’t worry, I’ve got your back.

Just like a frog starts out as one of those weird gelatinous eggs and slowly grows to a tadpole, then a froglet, then a full-on adult frog, the relationships people have with your company also develop over time.

When you first pop up on their radar, people may be unsure if they even need what you provide. Over time, though, that relationship can be cultivated and trust can be built. As alluded to above, emails are the best way to keep in touch across multiple points in time.

A word of warning

That said, many companies make the mistake of defining their lifecycle email efforts in terms of the emails themselves, rather than the relationship those emails exist to develop.

While lifecycle campaigns exist in part to keep your product in people’s thoughts, you would be doing your users and yourself a big disservice if you approached it as an opportunity to repeatedly blast your brand name at them.

You want to craft your strategy around key moments in the lifecycle and approach each email from a perspective of being as helpful as possible within that moment, not as a mosquito in their ear.

On the highway to user/product love, lifecycle emails are road signs providing timely guidance, not annoying billboards.

Matching emails to activities

Since the purpose is to bring people back into your product to continue their march toward victory, I’m a huge proponent of identifying what your onboarding flow’s most crucial steps are and then creating a series of emails that speak directly to those activities (as opposed to first trying to think up interesting emails and then sprinkling links inside them afterward).

For example, if your product is a dating website and you know that if someone doesn’t upload their photo they stand a very poor chance of generating any romantic inquiries, then crafting an email (or, even better, a series of emails — more on that later!) around getting people to do that one particular step is a very, very good idea.

Of course, aligning emails with actions is only good if the recipients actually take those actions, so let’s make sure these emails truly motivate.

What goes unopened goes unread

Startups tend to criminally underestimate the power of a compelling subject line. Just like many of the best marketers spend half their time on a blog post just writing its headline, a significant amount of time should go into a subject line that drives clicks. If your subject line isn’t piquing your users’ curiosity, it doesn’t really matter what’s inside the email — the recipient will never get that far.

Writing compelling subject lines is an art unto itself, but the best cheat code I’ve found for ones that lead to high open rates is to keep things as close as possible to the kind of subject line you’d send a friend.

This typically means keeping them brief, personable, and almost unprofessionally informal. For example, a subject line like “You there?” will almost always beat out “Our records indicate you haven’t logged in for 20 days.”

That said, getting email opens isn’t very valuable on its own if the content awaiting them doesn’t seal the deal in getting users back to your site.

You catch more flies with honey

Getting people to do things on the internet is hard enough, but getting them to do things that they don’t actually want to do is nearly impossible.

Before writing the email, make sure you’re not only clear on the action it will be triggering, but the benefit the user will get by taking that action. Too often, startups write from a self-centered perspective that commands the user, rather than entices them. Since you have absolutely zero leverage for negotiation inside a person’s inbox, it makes a lot more sense to seduce than it does to instruct.

Let’s return to the dating website example above, where you want your users to upload a photo. Rather than sending an email with a flimsy command like, “You haven’t uploaded a photo yet — log back in and add one!”, appeal to the value someone would receive out of doing so. “Did you know that profiles with photos get 6 times as many date requests? It’s true! Upload yours now!” would likely convert much, much better.

Don’t get in your own way

Another very common mistake is to crowd the body of the email with a bunch of nonessential chatter or extraneous links.

Emails designed to trigger a specific action should have sniper levels of focus and nothing else.

In fact, it’s very, very common to see action-oriented emails without a very clear purpose at all, often having four or more links, each kicking off a different activity. These come across as cluttered and distracted, and giving each of them equal prominence reduces the likelihood that any of them actually gets clicked.

Go with one rationale and one call to action — preferably as a huge, super-clickable button. Once your appeal has been made, it should be completely obvious where to click to take that action, and surrounding distractions should be left on the cutting room floor.

Oh, and while you’re teeing up your users with a big, fat button, make sure the words on it are pulling their weight, as well! Bland, directionless copy like “Sign In” or “Get Started” provide no information about what’s to follow or motivation around why they should click it to begin with.

In the dating website example above, “Start Getting More Date Requests” or “Complete Your Profile Now!” would both be much stronger options.

Don’t be a stranger, either!

Don’t forget that any given action can (and probably should!) have more than one lifecycle email associated with it. If your software helps people manage projects and they haven’t created their first project even after an email went out reminding them to do so, there is VERY little harm in sending them another one. Even if they were turned off by it (unlikely), it’s not like they were getting much value out of the product with zero projects, anyway.

Often, it’s simply a question of timing in your user’s life — everyone gets busy, and completing the setup of a product they signed up for a few days ago isn’t always a priority. As long as you’re sending friendly, considerate emails that speak to their interests, there’s a vanishingly small chance that you will be resented for being helpfully persistent.

Onboarding is no time to be shy. Keep things moving forward — it’s vastly preferable to radio silence followed by a “your trial’s about to expire!” email the night before they need to make the decision to pay or go.

Stack the deck in favor of a happy onboarding outcome for both parties by helpfully driving them to take care of their side of things!

Samuel Hulick is a UX consultant and the author of The Elements of User Onboarding. He creates a growing collection of onboarding teardowns at UserOnboard.com.

Related reading on the Help Scout blog

• User Onboarding Isn't a Feature
• Are You Making These 5 Common User Onboarding Mistakes?

Lifecycle Emails Are Magic Pixie Dust for User Onboarding was originally published in The Customer Service Blog By Help Scout on Medium, where people are continuing the conversation by highlighting and responding to this story.

“Revolutions have never lightened the burden of tyranny; they have only shifted it to another shoulder.”
 — George Bernard Shaw

Hey there, Slack. This won’t be easy, but it’s for the best.

As you and I both know, things started out so wonderfully. Me with my exploding inbox, you with your (very sexy) ambition to make email obsolete.

Only, I don’t know if we’re so good for each other, after all. Or, more to the point, I don’t know if firing up a relationship with you ever really fixed what was broken in my other one to begin with.

Everyone knows email and I had our issues. Email started as a frisky exploration into a whole new world and quickly escalated to a scale beyond anyone’s expectations. Next thing I knew, email and I had not only put a ring on it, we’d bought a minivan and moved into a little place in the suburbs.

Was it rushed? Sure. I think if we’d known just how big the relationship was going to become, email and I would have set things up very differently from the start. Still, a commitment’s a commitment, and we’d settled into a routine we could at least call our own.

Then, out of nowhere, here you come riding into my life like a goddamned Clint Eastwood straight out of Bridges of Madison County. The personality! The colors! You were all promises, rose petals, and sex appeal. And SO much more responsive to my needs.

Soon, we were messaging every day. It wasn’t long until it was hard to think of a time I’d ever gotten things done without you.

And that, really, was where things began to unravel for us.

Because, even though you’re one of the most enjoyable pieces of software I’ve ever jumped into bed with, I’m not sure you’re THE one, and that seems to be more and more of what you’re demanding these days.

Slack, you’re asking for A LOT of my time

I may have been fooling myself when we were still in the honeymoon phase, but when there was all the talk of you killing email, I have to admit I thought it was the email problem you were attacking, not just the email platform.

Which is to say, I thought you were providing some relief from the torrential influx of messages, alerts, and notifications I was receiving on a daily basis. “Me + Slack = Fewer distractions and more productivity,” I thought at the time. I have to say, though, that I’ve since found it to be the opposite.

Like, WAY the opposite.

With you in my life, I’ve received exponentially more messages than I ever have before. And while it’s been awesome to have such a connection with you, it has been absolutely brutal on my productivity.

I understand that it’s my responsibility to set boundaries in all my relationships, but every software product comes with its own bias towards supporting some human tendencies over others, and I don’t think it’s arguable that you skew pretty hard towards “always on” over “dip in every so often”.

I’m finding that “always on” tendency to be a self-perpetuating feedback loop: the more everyone’s hanging out, the more conversations take place. The more conversations, the more everyone’s expected to participate. Lather, rinse, repeat.

This really lowers the bar for what’s considered message-worthy to begin with. Email may have had its flaws with its “FWD: FWD: CC: FWD You have to read this!!1!” jokes sent from distant family members, but my god in heaven do those sound like the halcyon days of tranquility compared to the Diet-Coke-and-Mentos-like explosion of cat gifs, bot feeds, and emoji mashups you’ve brought into my life.

Even your summaries of each week — the ones where you remind me about how our relationship is going — are all predicated on its volume of messages, which was kind of the opposite of what I thought you and I were all about.

Just because it’s fun to hang out at the water cooler at work, it doesn’t mean I want to work there.

Kind of the opposite, in fact.

Actually, speaking of getting things done…

You’re splitting my attention into a thousand tiny pieces

While it’s true that email was (and, despite your valiant efforts, still very much is) a barely-manageable firehose of to-do list items controlled by strangers, one of the few things that it did have going for it was that at least everything was in one place.

Trying to keep up with the manifold follow-up tasks from the manifold conversations in your manifold teams and channels requires a Skynet-like metapresence that is simply beyond me.

With you, the firehose problem has become a hydra-headed monster.

Cabel on Twitter

Slack is amazing it totally replaced my e-mail inbox!!!! *secretly now has 95 separate inboxes*

Everything is scattered, and the mental load that comes with it is real. Linda Stone calls this perpetual, shallow quasi-presence “continuous partial attention”, and this makes each conversational thread, almost by definition, a loose one.

This isn’t so bad in the real world, where conversations have nuance and substance and context. With you, though, everything has roughly the same weight, so I find myself having to mentally maintain tabs on all my chats, be they consequential or not.

Speaking of loose threads…

You’re actually making it HARDER to have a conversation

Back before we met, I had two primary modes of digitally communicating with people:

1. Real Time
   Some of the digital platforms I used were inherently “real time” (phone, Skype, IRC, Google Hangouts, etc.), where there was a built-in expectation of an immediate, rapid-fire conversation wherein everyone involved was more or less fully-present and participating.
2. Asynchronous
   Conversely, there were other platforms that were inherently asynchronous (email, voicemail, iMessage, Twitter DMs, etc.), where there was no expectation of an immediate response, and people tended to send cogent feedback in their own time.

Then you came along, and rocked everyone’s world by introducing a conversational melting pot that is neither fully real time, nor fully asynchronous. You’re somewhere in between:

You’re asynchronish.

At first I thought this sounded delightful — it would be the best of both worlds! I was always free to drop someone a line, and if they were feeling chatty, a full-fledged conversation could simply spring up, with no need to switch platforms.

After getting to know you better, though, I’ve found that your “asynchronish” side is less impressive than I first thought. It leads to everyone having half-conversations all day long, with people frequently rotating through one slow-drip discussion after another, never needing to officially check out because “hey! it’s asynchronous!”

Jason Fried on Twitter

What would you call an all-day meeting with unknown participants and no agenda?

This leaves people spinning their wheels waiting for a response from someone who may or may not have already moved on to another discussion, with the problem only exacerbated by the fact that you don’t provide an indication as to whether that person is even currently in the same channel anymore, like by simply dimming their status dot.

Will they respond in 5 seconds or 5 hours? Who knows! It’s like getting caught in one of those support chats from hell with a Comcast rep who’s clearly trying to simultaneously jockey a dozen text conversations like some kind of bargain basement Bobby Fischer, except that it’s all day long and with everyone I know.

And, since you’re such a Swiss Army knife for conversation, it’s also often hard to get people to hop out of you to join a legitimate real time conversation, because it feels a bit too much like “booking a meeting” — since we can all Slack in Slack, why ever leave?

Actually, speaking of just that topic…

You’re turning my workdays into one long Franken-meeting

I think you and I can both agree that meetings are kind of the worst. And, on the surface, you do totally obviate the need for a ton of them. I can definitely think of many times in which a quick Slack whip-around has saved me from all kinds of interpersonal tedium. So thank you for that.

However, I’m wondering what the cost of it is. Specifically, I wonder if conducting business in an asynchronish environment simply turns every minute into an opportunity for conversation, essentially “meeting-izing” the entire workday.

All-day meetings every day of the week are substantially more “meetings” than the ones you’re saving me from.

There’s also a subtle side effect to asynchronish business, and that is its effect on the decision making process. When work gets done over email, there’s a general expectation of a response buffer of at least an hour or two. In you, though, people can convene and decide on anything at any time.

This is awesome for speeding up the tempo of company directives, but it also places a ton of pressure on everyone involved to maintain even MORE Slack omnipresence; if any discussion might lead to a decision being made, that provides a whole lot of incentive to be available for as many discussions as possible.

Even worse, those with the least on their plates can maintain the most Slack presence, which leads to the most gregariously unengaged representing the majority of the discussion base while penalizing those who are fully engaged in their “real” work.

Josh Pigford on Twitter

Reading the firehose of team chat is, categorically, not work, but it certainly *feels* like it. "I'm in tune w/ the team!" Nope.

More and more, you’re becoming something of a black hole for attention, sucking discourse and activity alike in with your massive (and very charming!) gravitational pull.

Speaking of black holes…

Lastly, you’re a bit on the possessive side

I will put this simply, Slack: not unlike Jake Gyllenhaal in Brokeback Mountain, I wish I knew how to quit you.

When I started feeling like our relationship was getting to be just a little too much, I decided to take a few days off. That was never a problem when I was with email — I’d just fire up a vacation autoresponder and be on my merry way.

With you, though, there’s apparently no option for deescalating our relationship outside of a few hours in “Do Not Disturb” mode. This means there’s no bigger-picture safety valve to make sure we’re not about to drive off a cliff hand-in-hand, like a socio-digital Thelma & Louise.

I belong to roughly 10 different Slack teams. People are very used to messaging me (directly or publicly) whether I’m online or not, so there’s a heavy social expectation for me to keep those conversational plates spinning on an ongoing basis, even if I’m signed out of all your clients.

I really don’t want to leave the people I care about hanging, but I haven’t seen any native way to let them know I may be gone for a while, and to perhaps try me elsewhere. This all seems a bit possessive on your part, whether you meant it to be or not — how do I take a vacation without taking you with me? How would you help me if I wound up in the hospital?

For better or for worse, you’ve gone from a novelty to a supernova in the blink of an eye. It’s only been two years, and many already act as if it’s impossible to remember what life was like before you came along.

You’ve become completely enmeshed in my social fabric, and I’m starting to worry about the effect you’re having on my friends, my colleagues, and even myself.

If you’re really on my side, you will not only let me experience life outside your embrace, you will even help me make it happen, trusting all the while that I will come back if it’s right. As they say, if you love something, let it go.

I’m sorry, but I need my space

Maybe you will say I’m afraid of commitment, but I’m just not interested in a relationship that seems to want to swallow up more and more of my time and attention, and demand that more and more of my interactions with other people go through you first.

I’ve stopped using you entirely over the past couple days, and it’s honestly been remarkable to see both how hard it’s been to disentangle from you from a social perspective, and how amazingly helpful doing so has been from a productivity one.

It’s hard to make this call, because I really do love so much about you. As a designer, I find you VERY attractive, both inside and out. Your user onboarding has always been world-class. Your copywriting even more so.

The question isn’t quality of design; you are stunningly well-designed in supporting the human tendencies you’re set up to support. I’m just not sure that those tendencies are ones I really want more of in my life right now. It seems that everyone’s social habits around using you are lagging pretty far behind your marvelous technical advancements.

If we’re going to get back together, I need to see you take the above on as a design problem. DND mode is a start, but there are so many other ways that design can help protect your users’ time and attention, both inside your interface and beyond.

Some ways have been alluded to, like dimming the dots of people who aren’t present, or allowing extended breaks via vacation autoresponders. I would also love to see not only how much time I’m spending with you, but how well that time was spent. Essentially, pursuing the UX maxim of “making it easier to do the better thing, and harder to do the worse.”

Because of your ethics, your commitment to user experience, and your astoundingly talented organization, no one is positioned to take the lead on helping our whole world communicate in a better — and saner — capacity quite like you are.

In the meantime, you can always reach me via email, or on Twitter at @SamuelHulick.

Illustrations by Michael Buchino • buchino.net

Words by Samuel Hulick • useronboard.com

A recommendation would be very nice.