UserOnboard EXPOSED!

An Unlikely Story

From the start, UserOnboard has been a life-changing project.

In the autumn of 2013, I created a couple SlideShare presentations to promote a project I was working on, and they quickly became more popular than anything I'd ever made before.

After getting some sage advice on the virtues of self-hosting your content, I thought "you know what? I bet I could crank out a standalone website for these over the weekend."

I found an available domain name ("" was already taken, so I got "") and whipped up a quick (aka "janky as hell") hand coded slideshow feature. It was off to the races immediately thereafter.

I was *shocked* at how quickly things picked up steam, with interest coming from several corners of the software design world. I kept producing slideshows, and each one brought in more and more interest.

A month or two in, I distinctly remember dry-heaving with nerves while on a call with a high-ranking design exec at a company that rhymes with "Netflix" (ok, it was Netflix).


Almost five years and more than 60 slideshows later, there have been over 1 million unique visitors, and it's led to some immensely rewarding professional opportunities.

It's also been kind of wild to see how far this crappy little "weekend project of a website" has managed to keep rattling along for.

In fact, I've almost intentionally kept the UserOnboard website crappy, just to remind myself of what can be accomplished with a tiny helping of PHP and elbow grease.

But you know what? ENOUGH OF THAT!

It's time to practice what I preach.

It's Time to Improve My Own Damn Onboarding

There is a profound irony in creating a website dedicated to critiquing UX oversights in popular products, but completely ignoring those same principles in your own.

In fact it's, downright hypocritical, isn't it?

For whatever reason, it didn't even occur to me that UserOnboard would HAVE onboarding of its own. I'd always thought of it as more of a "blog" than as software, and if people don't experience "activation" with a blog, what was there to even think about?

"Well, dum-dum," I realized embarrassingly recently, "you have at least THREE things that people already are being 'onboarded' around. There's an email list that people sign up for, and a book that people buy, and a consulting service that people hire you for -- how do you think those people wind up that way?"

I didn't like being called a dum-dum, but I did have to admit that I had a point.

As the web continues to evolve, the line between "content" and "software" has become more and more blurred: is an ecommerce purchase a "software" experience? Is taking an online course one? Why can't a blog deliver as transformational of an experience as any other digital medium?

I mean, airplanes clearly aren't software, and they still have onboarding -- that's where the term "onboarding" comes from!

And either way, wasn't I the one who kept saying that onboarding wasn't about the "product" to begin with, but about the improvement it brings to someone's life?

Like... didn't I literally say that in that silly Super Mario graphic I made years ago?


Clearly, there's a desire in many, many people to become a "fireball-throwing Mario" when it comes to their own user onboarding skills -- but how much is UserOnboard as a website actually helping them get there?

Well, I have two answers to that:

  1. By its own definition, UserOnboard's user onboarding totally sucks
  2. I now plan on changing that in a major way

A New Journey Begins

Over the next couple years, I intend to not only apply everything I know toward improving UserOnboard's own onboarding, but to actually turn it into a living showcase of best practices to follow.

I plan on approaching this in an iterative, experimental way, and here's the kicker: I'd like to share each step of that process right here with you.

Do tooltip tours really work? What's the ideal timing for a welcome email? What are effective ways to research user motivations during key stages of the signup process?

In short...


( Except instead of hoping to survive on potatoes grown out of my own poop, I'm hoping to design an ultra-effective onboarding experience so everyone can take the insights learned and apply them to their own design process. So... slight difference there. )

While every experiment won't necessarily be universally-translatable, I do plan on being as transparent as possible with the results, even when (and especially when) sharing them doesn't feel so great.

Speaking of results, I like having goals for any project I take on, and this one is definitely no exception. Outside of "learning and sharing" as a general process, here are four outcomes I'm orienting around:

1. I'd like to generate actual business results

I will be "my own client" in this case, but that doesn't mean I plan on ignoring my responsibility as a designer to produce biz outcomes. And like any other metric, I plan on sharing sales numbers transparently each time they change in a significant way.

Right now, UserOnboard's book sales generate a few hundred dollars per week, so a goal of 10x-ing its current revenue would mean roughly $4k per week. I think this is a good number to shoot for, because it's somewhere between "reasonably achievable" and "ambitious enough to make me feel kind of queasy", which is the line of demarcation I usually use for making big decisions.

To get there, I will apply my usual process of user research, rapid prototyping, and experiment-driven design for improving every step of a person's path to onboarding success, just like how I'd approach any onboarding design project (how meta!).

In addition to that, the process will also likely include creating new educational products for sale here (like, for example, interactive courses on advanced onboarding techniques). This seems like a win-win for everyone.

Also, this means I can call it "slouch to $4k" in my head, which is very funny and amusing to me.

2. I'd like to help spread the word, further and better

One thing I've noticed since all the way back when I started is that many designers are really interested in onboarding case studies -- especially ones with numbers attached -- and that many companies are EQUALLY interested in keeping those ultra-sensitive user acquisition numbers under tight wraps.

Well, not me! I don't have any investors to placate or funding rounds to "crush", so my level of "not caring about sharing numbers" is roughly zero. Oh wait -- the opposite of zero. I "100% don't" care about it.

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Beyond that, I'd like to curate a lot of external success stories, as well; if I do this right, the world will have a lot more "fireball-throwing Marios of user onboarding" out there, and helping to signal-boost any stories they'd like to share would make my heart very happy.

I don't want to get too mushy on you, but one of the great lessons I've learned in life was to internalize the mantra of "my success is the success of others", and that definitely applies here.

On that note...

3. I'd like to contribute to a broader discussion about the ethics of design

My "science the shit out of onboarding" plan will, by definition, involve experimenting on the designs that people experience. This means that I will be, in a not-so-indirect way, experimenting on people, period: what does it look like to do that ethically?

In the wake of things like Facebook's Cambridge Analytica scandal and Europe's GDPR ruling, concepts like privacy, consent, and user manipulation are finally becoming top-of-mind for more and more of the general public (and thankfully so!). I see this as a great thing, but there isn't exactly a plethora of templates out there right now for designers to follow in navigating that emerging landscape.

I definitely won't claim to have all the answers, but I do have a whole lot of questions and I'm excited to help develop the publicly-accessible info on this subject by exploring them. I'm also interested in exploring how sharing my process publicly and transparently affects my design decisions, and especially what it means if that leads me to decide to stay away from techniques/patterns that are otherwise very popular in our industry.

For now, I think a good guiding principle is "don't do anything you'd be embarrassed about if your users found out it was happening," and I also aim to amplify that by straight-up telling everyone what I'm doing, as I do it. What follows from there will depend a lot on the feedback provided, both qualitatively and quantitatively.

And lastly...

4. I'd like to cultivate a community approach to all of the above

I have zero community management experience and am pretty sure my introverted self will suck at it pretty righteously, but I can't really imagine approaching this as anything other than a two-way street.

Each update I post will have a comment section like the one below, and I'd love to explore starting a public discussion forum, etc. in the near future. Either way, your feedback is not only accepted, but heartily encouraged. If you have something critical to say, so much the better -- we're all just figuring this out together either way, so as long as it's constructive, it's more than welcome. Ditto for ideas and suggestions on other techniques to test, ideas to experiment with, etc.!

Also, the more people who participate in general, the more quickly the experiments can reach statistical significance, which means I can share the lessons learned that much more quickly as well. So (ahem) ... please help spread the word by sharing this with anyone who might be interested!


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I'm really excited to share this with you. And it's only the beginning. The next few months of experiments are already planned out, and some of them are even underway as I type this.

If nothing else, we will all come away with a better, more useful experience here, and a whole lot of lessons learned in the process.

If you're interested in contributing by commenting, sharing, or simply following along, I'm already more than thankful. Here's to the next stage of each of our journeys.


Here is Update 001! And here is Update 002!