User Onboarding

On May 8, 2015, I read Samuel Hulick's excellent book User Onboarding. Had more than one aha moment. Below are some of my notes.

"When you design for intents, you harness the only source of energy driving a web experience - the user's motivation to move forward."


Onboarding users is equivalent to guiding them from the bottom of a mountain covered in fog, to its peak, from where they can see the entire mountain because the fog has dissipated in the meantime.


People want to know how your product will be a meaningful addition to their lives. Establishing your product's value in its attributes (features, performance, etc.) forces people to piece that meaning together themselves. That's tedious for them and risky for you - how do you know their interpretation will be accurate? When you instead talk in improvements, you're handing them a complete picture, not a puzzle to put together.

What if you could instead generate that "aha moment" before signup, when it can happen for many more people? How could you create the mental connection of how your app will get them to that desirable place, without having to pull them all the way through it to figure it out?

The key is to get them to understand your product in the context of their own lives. "Wait, I can rent movies without going to the video store?" "Hold on, I just drag my files into this one folder and they're automatically on all my devices?" "Whoa, I can have super strong passwords without having to remember any of them?"

Ideally, your pre-signup touchpoints allow your users to envision not only the improvement you provide, but also specifically how your product helps them get there.


Show the app's place inside the context of real-world workflows.

If your earliest touchpoints sell the dream, your following ones should help ground it in reality. A high-level value proposition like "the best way to publish your social media updates" might be intriguing, but if you then fail to answer even a simple question like "ok, how?", the whole thing quickly unravels.

Instead, consider how legitimized that value prop becomes when you follow it up with something like "you save your updates as drafts with us, and we publish them on your behalf at the the exact best time for your audience." You just went from "dubious claim" to "Buffer" in 24 words!

Whatever human need your software fulfills, you can bet your visitors are already satisfying it, one way or another. Unfortunately for you, people tend to dislike change, especially when they're the ones who have to start doing things differently.


Don't assume your only competitors are companies that make products similar to yours. In fact, it's much more likely that your users are currently solving their problem with something they've cobbled together themselves, and are only now seeking outside help because they've stressed their own system to the breaking point. In that way, your true field of competitors widens to such ingrained incumbents as pen & paper, telephones, email, and Excel. Considering the fact that we're also dealing with an extremely limited amount of attention to make our case to, let's throw showstoppers like apathy, confusion, and the back button into the mix, as well.


When dealing with emotional forces, appeals based on logic and reasoning aren't very effective. Humans are irrational beings, and the non-rational side of the human psyche is, well, super not rational.

Ultimately, what you want to accomplish are two sides of the same coin: you want to connect with them by showing you understand their current struggle, and you want them to forge an emotional connection with the superior option you provide.


Acknowledge the users' pains: If your product is project management software and you find out your customers are concerned with administrative overhead, acknowledge the nightmare that group emails can cause. Ultimately, you want to play the role of a dentist picking at the raw nerve of a rotten tooth - poking their Elephant's awareness of the less-than-optimal situation until its previously-unmovable inertia 180s into a relentless force for self-improvement.


An activity like web browsing has us perpetually in "scan" mode, and human faces are like magnets for that, pulling our primal attention away from safe and boring things like text and screenshots.

"People want to believe that they make decisions rationally, logically -but in reality, they make them emotionally first. Then they defend those decisions with logic." - Tom Hopkins, sales trainer


Successful testimonials include four elements:

  • Face: As we've covered, they're lightning rods for attention and and an emotive, human-to-human punch
  • Name: Including the quoted person's name provides a level of authenticity that something like a Twitter handle simply can't
  • Title: Is this person the Vice President or a parking lot attendant?Titles help inform the reader how much authority is behind the recommendation!
  • Logo: If the person you're quoting is representing a super recognizable company, including that company's logo will provide an excellent shortcut to credibility


If you have the power of numbers on your side, let prospective users know there's safety there! Showing signs of a thriving user base tells those on the outside that you're onto something - where there's smoke, there's fire. It's for this same reason that restaurants seat people at street-facing windows first: restaurants that appear crowded are probably crowded for good reason.


!:What you really want is to show that you're frequented not just by lots of people, but lots of the right people. People your prospective users identify with, and perhaps even aspire to be. One way to achieve this is what I call the "jeweler to the stars" approach: openly stating that you're in existence to serve a specific and aspirational audience. This not only lets the "stars" know that this is the place for them, it lets people who want to be stars know that they should be frequenting there, as well. Framed inside that context, abstract numbers like "follower count" become a lot more powerful.


The first order of business is to take a long, hard look at the most critical of all the attempts: the first one. We want this experience to be extremely well-curated, because software products across the board have absurdly high abandon rates after the first use.

"No matter how great your product is, it is very likely that 40-60% of your free trial users never see the product a second time. Which makes that first use of the software really really freaking important."


Going back to the mountaineering metaphor, you can almost think of our goal for the first visit as simply getting them to reach a "basecamp" partway up: a small win that provides them with a positive outcome to their first excursion, and one that can be used as a springboard for future efforts.

Like at the ice cream parlor, offer a sample taste of success

What you lead off with sends a very strong signal of "this is the most important way to engage with this product"

Case in point, Twitter saw a massive spike in signup retention once they stopped leading things off by encouraging people to search (no one came with a search in mind) or tweet (nobody was ready to tweet right away, either) in favor of following (everybody knew people they were interested in).

To boil everything down, think of it via this litmus test: what's the one first step in your software that, if you knew someone took it, would make you feel WAY more comfortable in betting on them ultimately becoming highly-engaged users?

as designers, it's easy to take the steps in any workflow for granted. Instead of taking a step back and finding the shortest path to a real-world outcome, it's easy to simply define progress as "making it past the steps in our workflow," as if the act of advancing through an app's setup wizard had value unto itself. This is a mistake ,because not only can steps have little correlation with actual achievement, they can actually be preventers of it.

One way to mitigate that is by anchoring the limbo material on top of the aforementioned "real" interface. Quora does this when it asks you to start things off by picking out interests:

[image of interests selection form with Quora blurred in the background]

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


One trick for designing compelling and relevant interactions is to imagine yourself standing in for the website and personally helping the user with their improvement. How would you introduce yourself? What are the first things you'd help them accomplish? Are there questions you'd ask them right off the bat? What would your tone be?

Getting a really clear idea on how you would behave in that situation can make for a phenomenal starting place for planning out how the website will behave. In other words, figure out the human-to-human interaction, then design the human-to-computer one to mirror it. When in doubt, ask yourself "what would I do if the user was standing right in front of me rather than sitting in front of my website?" Then design the site to replace yourself.

If your interface is so confusing that it needs more interface just to introduce itself, my recommendation is to have not so confusing of an interface to begin with. Tacking callouts on top of a poorly-designed UI does not fix the UI, it just literally points out how poorly designed it is.


If you're already using coachmarks (overlaid tooltips that explain UI elements), try this as an experiment: turn them off, and bring in some people who've never used your product before. Watch how long it takes them to figure out what the purpose of the UI is. Note the biggest areas where they trip up.

Then, instead of turning coachmarks back on, fix those points of ambiguity and confusion to make them not ambiguous and confusing! The way to get a floundering UI to reliably stand on its own is to strengthen its weak points, not to prop them up with lots of little crutches.


Be positive and offer calls to action, instead of dry errors. Rather than pointing fingers and bluntly saying "You have no friends", use that state as a point of encouragement in and of itself: "Add friends now".


There's a famous (and pretty amusing) clip from Candid Camera where a mark would be standing alone in an elevator and actors would trickle in all around him. Instead of facing the door like normal people, though, the actors would all face one of the walls. Sure enough, the original person (the non-actor) would turn to face the wall, as well! Social pressure can be pretty compelling!


If you take a big goal (whatever the "base camp" during climbing the mountain is) and chop it up into smaller, more immediately-achievable tasks, you lay out a series of "impulse buys" that many people will find very hard to resist. After completing one trivial step after another, they suddenly find themselves fully up and running.

Like the "displaying guidance from others" approach, this also takes the onus off the user in figuring out what they should be doing in order to explore the product's core activities - you're literally telling them "these are the most important things to do right now."

From a UI perspective, this is typically accomplished with something that resembles either a to-do list or a completion meter (aka progress bar). What they look like isn't really the important part, though - it's what they do: get more people to complete the task at hand by explicitly stating the steps a user needs to take, and reporting on their progress as they go. A good example is LinkedIn's profile completion % and steps.


Setup quests are actually the opposite, in that they encourage exploration in the product, and (mostly) self-directed accomplishments. If wizards are like soapboxes for the product to stand up and introduce itself, these are more like scavenger hunts.

Quora is making heavy use of something called the "endowed progress effect", which is a psychological phenomenon that basically boils down to this: the closer people think they are to completing something, the more likely they are to actually see it through.


A criminally-undervalued aspect of product design is the act of simply acknowledging that someone has achieved something important or complex (or both). Their brain, knowing it just did something good, is flooding with positive chemicals - be the thing that it bonds with in that moment, not a stone wall it has to workaround.

Positive encouragement costs you absolutely nothing to implement and can provide outsized effects on emotional adoption. Plus, remember the Peak-End rule from Chapter 9? We want to make sure people know darn well how swimmingly things wound up!

Also, a post-success message is the perfect time to slip in a few additional recommendations, a la "while we have this good thing going, how about uploading a profile picture?" It very well may find them in a receptive mood.


Delay the welcome email a bit


An interesting variation of the "you're making progress" email is when it's triggered by something someone other than the user themselves did. Medium's "your post is on the move" and LinkedIn's "someone endorsed you" emails are both stand-out examples of positive encouragement that was initiated by someone else's activity.


Finally, we have the "you're running out of time!" message type. These are typically set to pop slightly before a trial period is going to end, and attempt to play on people's sensitivities regarding loss-aversion and urgency in order to get their action initiated (that action usually being to start paying for the product).

These can often come off as a bit desperate, especially if it's one of the first times you're getting any email from that company at all. Likewise, if the other three emails are doing their jobs (especially the first two), then this one won't be super necessary.


Hoping that a "your trial's expiring" email will spike sales among people who've never even finished their setup process is doomed from the start. For a robust, high-vitality user, though, it's a pleasant reminder of how far they've come. If all went well, cementing your relationship isn't even a decision for them at that point - it's simply a reflex of realizing the enormous value you're providing.

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