Samuel Hulick has been a central figure in bringing user onboarding front and center for modern software products.

A UX designer by trade, he is regularly publishing detailed onboarding teardowns of everything from productivity tools like Asana and Trello to Ashley Madison and the Hillary 2016 campaign app. You might also recognize Samuel’s name from our new book, Intercom on Onboarding, for which he was a guest contributor. He’s written his own book on the topic too.

Samuel joined me on our podcast to discuss why your onboarding must concentrate on the user over your business, the importance of revisiting your onboarding, where we can find onboarding inspiration outside of the software world, and much more.

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What follows is a lightly edited transcript of the interview. Short on time? Here are five key takeaways:

Onboarding is an outcome – successful users. It’s less a question of getting users from A to B in your app and more from A to B in their lives. If treated like the launch of a discrete feature you can walk away from, rather than an evolving element of product-market fit, the effectiveness of your onboarding will wain. Samuel sees software is an environment for accomplishment. Any time you design an environment it’s going to have a natural getting started process. Thus, we can find onboarding inspiration everywhere from the supermarket to slot machines. In the B2B software world, there are two primary onboarding experiences: the first person who must create an environment of success for everybody else and the follow-on onboarding users who must make sense of what they’re supposed to be doing. As soon as your product appears on someone’s radar and they recognize that it could help them – via word of mouth, advertising, a marketing page, etc – that’s where onboarding starts.

Geoffrey Keating: Samuel, welcome to the show. We’ve been huge fans of yours for a long, long time. Can you give us some quick insight into how you started your career and what drew you to onboarding?

Samuel Hulick: I started my career as a user experience designer roughly a decade ago. What drew me to that was looking at software as something that can provide superpowers to people, where you have these capabilities that you wouldn’t have otherwise.

Being in the user experience design field, one area that I noticed could really use a lot more attention was the user onboarding process, or the process of getting people transitioned from being unaware of what your product can provide to them taking on the fullest capability that your product does provide.

Geoffrey: What do you actually define as user onboarding? I know your definition is slightly different than a lot of others.

Samuel: A lot of times when you ask people what user onboarding is, they’ll say that it’s something like a tooltip tour, the introductory material or some help documents. While those can be beneficial for getting people up to speed with your product, I really look at it less from a standpoint of dragging people by the ear to activating features or click “next” 20 times in a tooltip tour. It’s actually more along the lines of getting people up to speed with the better version of themselves they’re hoping they will become with your product in your life. It’s guiding people toward that up and running, cool and capable stage. It’s less a question of getting people from A to B in your app and more from A to B in their lives.

Geoffrey: So if it’s not just about signing up, how do you build an onboarding to make sure users keep coming back?

Samuel: It’s really crucial to have a great first-run and sign-up experience. The first 5 minutes of your product are really, really important. If you don’t make that great first impression, it’s very unlikely that they’ll come back nearly as willingly as they did before. Nailing that is really paramount. But of course, it’s also a matter of building up habits in people’s lives and getting them all to be as successful as they possibly can be.

By definition that probably isn’t going to happen in one single sitting or within a couple minutes, and would require getting people to come back into your product. A lot of the onboarding-centric product designs patterns like tooltip tours can’t get people back into your product because they are in your product to begin with. You need to go find people where they are and entice them back in. The two major tools I’ve seen to do that are notifications within a mobile app and lifecycle email.

Targeted, well-timed messages are the best way to keep onboarding moving forward

Your onboarding must evolve

Geoffrey: Many of our listeners are at early-stage companies and may have only recently designed their onboarding experience. It can be tempting to design an onboarding experience and leave it alone. How often should companies be revisiting their onboarding?

Samuel: I’ll speak with companies and they’ll be excited to say, “In Q2 we’re going to launch our onboarding.” It’s always a little something that I wince at, because it sounds like they’re treating it as the launch of a discrete feature you can walk away from. They’re not necessarily looking at it as an evolving element of product-market fit.

In the same way that you wouldn’t launch customer support and then be done with it, you want to have your user onboarding – especially if you’re not looking at it as the definition of some pixels that show up on a screen but rather the process of helping people become successful while adopting your product – to evolve as your market evolves and your product evolves and your customer base evolves. It’s something that ideally involves constant iteration and evolution.

What onboarding in the real world can teach us about software

Geoffrey: Onboarding in one way or another has been around for hundreds of years. Do you find yourself analyzing onboarding experiences outside of software and in real life, even at the grocery store for example?

Samuel: Absolutely. I would say much longer than hundreds of years probably. A lot of times what you’re creating when you’re creating software is less of a tool and more of an environment for accomplishment or activity. Any time you design an environment it’s going to have a natural getting started process where people are figuring out what it is they need to be doing and how.

One of the best IRL onboarding examples is when I get out of town and rent a cabin on Airbnb. When I arrive maybe I’ll have phone service or maybe not. How easy is it to find where the key is or the key code is located? If I do get in, can I find how to turn on the lights and the heat? Do I know how to access the internet? If it comes with a sauna do I know how to turn that on or not?

A lot of times you’ll find that the hosts have clearly anticipated all of the questions someone might have upon entering the environment of their house, and everything is laid out right where someone would most intuitively encounter it. Other times it’s a complete nightmare. You have to find this one scrap of paper that’s hidden underneath a shelf.

It’s a very similar process where you’re looking to transition people into the mode of life that they were hoping to receive when they decided to pull the trigger on (a purchase). Sometimes you can do that really reliably, and sometimes, if you don’t pay a lot of attention, it becomes painfully obvious.

Geoffrey: That’s probably the challenge for some of these on-demand companies – some of the variables are out of your control. It’s a two-sided marketplace. How do companies like Uber, Lyft and Airbnb design around that?

Samuel: The design responsibility is as local as the control is. If a host wants to get good ratings and get more people to come and have more positive reviews they can approach it in a conscious, considerate and hospitality-oriented way. If they don’t decide to do that then they will suffer whatever types of consequences the marketplace determines based off that. I can imagine that being a concern for Uber or Lyft or Airbnb, but at the same time what they’re creating is a larger system that hopefully has some self-regulation to it.

Geoffrey: What can we learn from industries outside of software? Slot machines and video games are two industries well adapted to user onboarding and retention.

Samuel: In both cases those have been very influential in my study of onboarding and the research that I have done in my own life. Video games have arguably been around longer than software, at least in the mainstream, and in a lot of ways the getting started experience is a little bit more mature and articulated in that medium. There are things like first-level design and tutorials that are part of games and things like that. I’ve been able to draw from a really rich pool there in terms of insights and inspiration.

Natasha Schull explains how casinos onboard their customers

You mentioned slot machines. There’s an amazing book written (about this) by Natasha Dow Schull, Addiction by Design . If you look at casino floor layouts, their climate control, lack of clocks, things like slot machines and even free-to-play games like Candy Crush, they have really gotten people’s brain chemistry figured out and turned addiction to a science. It’s regrettable in a lot of ways, as far as the predatory and Machiavellian practices they employ, but at the same time what they’re learning can just as easily be used in service of helping people become successful.

Ignorance is not something to your benefit, so learning the tools that people who maybe have more questionable ethics are using can be helpful, as long as you’re following your own Hippocratic oath.

Geoffrey: Particularly in terms of casino design, there’s such a fine line between what we can take inspiration from and some dark patterns.

Samuel: Speaking personally for myself, I take inspiration from all of it. It’s just a question of filtering it through my own litmus test of ethics. That’s really the question that I come back to time and time again as a user experience designer, especially when looking at how to persuade and motivate people into taking actions and getting into the field of behavioral economics. If you are really able to have a profound affect on people’s behavior and nudge them in one direction or another you’re going to need to have some guiding principles around that.

Setting up business vs. consumer users

Geoffrey: What types of differences have you noticed in designing onboarding flows for business apps versus consumer apps or consumer products?

Samuel: There’s less of a difference between the two than one might think upon going into it. The biggest difference is the lifetime value of a customer for business software is typically 10x or more of what the lifetime value of an individual user for something like Twitter would be. Therefore when you’re looking to create something that’s more consumer-oriented you really have to rely on the self-serve experience of the product to be able to carry the day. You won’t be able to put the resources of people’s time or employee time toward going in and helping walk people through in some sort of intimate, white glove kind of way. You may be able to justify that for something that’s more B2B-oriented. If the lifetime value of a customer is $6,000 or $60,000 you can certainly afford to put an accounts person on that and help walk them through whatever rough edges your user experience might have. At the same time, it’s great to have a product that people will crawl through broken glass to get to, but it never hurts to get rid of the broken glass.

In both cases if you can have a really intuitive, immersive and, most of all, valuable self-serve experience, it’s not going to hurt the bottom line.

Geoffrey: How does that translate to the enterprise level?

Samuel: Enterprise is an interesting beast. I’ve worked in that capacity myself, and when the person making the purchasing decision is further removed from the people who are using the product the emphasis on user experience tends to suffer. The bigger the organization and the more the bureaucratic red tape involved, the more you’re going to find that the onboarding “experience” is more like golf trips and steak dinners and less about self serve and having a high quality experience for the people that are actually using the product.

That can be regrettable in some ways but it also seems to be the fact of the situation. There are a lot of enterprise companies who offer training for their own product and that’s actually a revenue center for them. It’s almost against their own interest to provide a really compelling product that can explain itself and be used in an intuitive way.

Enterprise onboarding, especially for a demo and the long sale cycles, is something that I tend to not focus on much. I focus more on B2B and B2C.

Geoffrey: Just to clarify, you’re talking about IBM and the Oracle model, where training is often a consultancy and becomes a revenue business in itself?

Samuel: Yeah, I haven’t looked into that recently, but I would imagine there’s some sort of micro economy around providing professional services and things like that. Certainly not to throw any of those companies under the bus; it just seems to be a different model than providing something that people can use on their own.

Onboarding in groups

Geoffrey: Traditionally when we think about onboarding we think about one person in front of a computer. At Intercom we’re actually having to consider onboarding groups of people, all with different abilities and different roles to play in that onboarding. Have you noticed any good examples of how to onboard groups of people rather than just individuals?

Samuel: I don’t think that’s a particularly new challenge. I would have to imagine back in the Windows 95 days getting people to pick a platform on the OS level or decide whether or not they’re going with Microsoft Office was a group decision that involved a lot of employees and people of different hierarchies within the company.

The problem is ultimately the same when you’re designing B2B. You’re probably not designing for a single user, and even if you are, they probably need to be able to make a case to their boss to allocate the budget, or they may need to work with the IT department to make sure it’s up to safety standards. They might have to convince their other employees to jump on and work with them in that product, so there’s a lot of political maneuvering that may need to take place.

It’s a people problem just as much as it is a software problem.

That’s an absolutely huge onboarding opportunity. If you can arm that particular person with some really compelling sales material, then when they do go to their boss and make a case for the budget needs, you’re not just relying on them to be the best salesperson they can off the top of their head. You’re helping grease the wheels.

If you need to onboard an entire team than you need to be really attentive to the different start-up modes. If someone wants to start using a bug tracker or a project management tool like Asana, they would probably go in and sign up and be in what I call “homesteader mode”, where they’re going out in the frontier to set stuff up for other people to follow. Then most likely they’ll invite the rest of their team to come in.

You really have at least two primary different onboarding experiences. There’s the first person who’s going in and trying to create an environment of success for everybody else, and then there are the follow-on-invitation onboarding experiences for people who know substantially less than that first person did and try to make sense of what they’re supposed to be doing, why they were invited, what this product is, what it does, what their role in it is, etc. That’s absolutely something to pay a lot of attention to.

Geoffrey: So one of the challenges is equipping that onboarding champion with enough materials to get everyone else onboard with the particular piece of software?

Samuel: Yeah, whether those other people are actually directly using the software or not. One question that I like to walk through as an exercise when I’m consulting with companies is, “Who does this person care about looking good to, what does looking good look like, and how can we most reliably demonstrate that looking good is taking place for them?” It’s a people problem just as much as it is a software problem.

Where onboarding sits in your company

Geoffrey: Your onboarding teardowns cover all sorts of products from Basecamp to Ashley Madison. What I love about your teardowns is they always start on the marketing landing pages rather than the first few screens after a user signs up. From a organisation structure, where does onboarding sit within a company? Marketing? Product?

Samuel: It’s tricky, and that’s one reason why onboarding can fall through the cracks for a lot of companies. There’s something called Conway’s Law. The short version of it is basically that the thing a team produces will be organized in way that reflects the way that the team was organized. So if there wasn’t anyone who “owns” user onboarding than that will probably be something under-emphasized in the end result product that’s being created.

Onboarding is an incredibly valuable part of the overall product experience. Having someone be in a position to either own that as their full-time responsibility makes a lot of sense to me.

In regard to starting the onboarding review on the home page or in the marketing material, I really look at that as a cycle. Ultimately if you’re onboarding people well you’re putting them in a position to succeed or to thrive to the best of their abilities with your product and their life. What you’re really hoping to generate is product evangelists who are just getting everything they possibly can out of it and have found such success that they are preaching your name from the mountaintops. “Hey, your life could be so much better if you also used product blank.”

What I really consider onboarding to be is the process of getting people from the first time that they heard that your product could help them all the way to your product actually helping them. That might come through word of mouth, which is a very high ROI approach to customer acquisition. It could also come through a radio ad, a Google or Facebook ad, or SEO, but as soon as your product pops up on someone’s radar and they recognize that your product could help them do something better, that’s where onboarding really starts. That’s where the seeds of what your product promises are starting to be planted.

Geoffrey: One of the biggest problems is that you’ll often see very inconsistent transitions between marketing pages and the time you sign in. The challenge for a lot of companies is smoothing those transitions between marketing and growth, who might own a different part of the product, and the product team that might own a completely different part. Actually designing a consistent experience that feels completely seamless throughout that onboarding experience is difficult.

When several different teams own a different piece of onboarding, make sure silos don’t emerge.

It can definitely feel like a multiple personalities situation. Going from an advertisement to the home page to a landing page to a sign-up page to the first use of the product to ongoing use and into the billing form for example, that might feel like six or seven different products. If you are going through one of those experiences and you come across a really high contrast transition – aesthetically, branding wise, interface wise – there’s a good chance there were very different personnel involved in creating those two high-contrast experiences.

A lot of times it’s like you’re actually working with two people as soon as you click the next button and are taken to something that’s completely different.

Geoffrey: One of my favorite analogies that you use in your writing is that of tricycles versus training wheels – that it’s actually possible to actually cripple your product by making it so easy to use. Could you explain that?

Samuel: I can’t take credit for that particular metaphor. That was introduced to me by Kathy Sierra. The idea is that if you were to just hand someone a bike then they wouldn’t immediately be able to take it on and use it to the best of their ability. There’s some training that needs to take place. Training wheels can be really helpful, but one of the best parts about training wheels is you can actually get rid of them when they’re no longer relevant.

Unfortunately that’s not the case with a tricycle, where it is easy to get started right away, but if you’re only focused on making the Fisher Price “My First” version of your product, people are going to get bored with it relatively quickly. Although it was easy to take on, it is pretty limited in what you can do beyond that. It’s similar to picking up a guitar or a violin versus playing Guitar Hero. One is a lot more accessible but accessible doesn’t always mean that you’re going to have a really long-term retention by helping people succeed in a way that’s markedly different to how they’re already approaching things.

Geoffrey: It’s funny you mentioned Kathy Sierra actually because some of your writing reminds me of her mantra – making users awesome.

Samuel: She has been incredibly influential in my career and my mindset as a designer. I would unhesitatingly recommend anyone to look into the work she has put out.

Supplementing the onboarding experience

Geoffrey: We’ve see products like Quartz and Slack, where the product is actually it’s own onboarding. With a feature like Slackbot, you’re able to learn without feeling like you’re being taught. What do you look for in high quality onboarding and what role do you see for things like in-app messaging and bots?

Slackbot, as seen in Samuel’s teardown of Slack’s onboarding experience. See the full teardown here.

Samuel: When I find that the quality of the onboarding experience tends to be not well considered or thought out, it’s really clear there’s the core use of the product; and then completely separate from that there’s another interface that’s been slapped on after the fact. A lot of times that’s pointing out areas where the product team realizes that the product might not be super intuitive or very obvious in how it’s guiding people to do the important things that people need to do.

What I find to be one of the biggest hallmarks, if not the hallmark of quality onboarding, is to blur the lines between the core use of your product and the introduction of your product to the point where people can’t really differentiate between the two. It feels like one cohesive experience.

I use this metaphor: If you were designing a plane the primary use of it would be to fly. But if you’re only designing it for that you wouldn’t include a door, because you don’t need doors to fly, and you wouldn’t include wheels, because you don’t need wheels to fly. If you have a plane that you can’t get into and can’t get off the ground then it’s basically as valuable as no plane at all.

The idea of developing the entire experience from the beginning, starting your design where users start their use and going forward from there is really, really crucial. If you can’t get people through the first five minutes of your product, it really doesn’t matter what amazing features you might be working on. For the people who aren’t making it there they basically don’t even exist. That’s really what I look for in high quality onboarding and high quality product design in general.

Regarding bots or messages that’s something where, through products like Intercom, if you have a human being who’s there and conversing with people, it can be a really rich source of insights and help provide that just-in-time assistance that someone might need. If you can automate that with something like a bot, that’s wonderful. At the same time, when I look at conversational UIs, I see them as being much more valuable from a learning standpoint for the company than necessarily for the user themselves. Hopefully when you are having these conversations you’re picking up on patterns and pain points in your product and turning those insights into actual product changes that everyone can experience at scale from there on out.

From teardown to improvement

Geoffrey: Things like your teardowns and other sorts of unsolicited redesigns have played such a big part in design criticism over the past ten years. Have you found the feedback you’ve given to companies being incorporated into products? Or have you had any push back from other companies over things you mentioned in your teardowns?

Samuel: I totally hear where you’re coming from regarding lumping teardowns and unsolicited redesigns together. At the same time as a designer it does make me wince a little bit, because I tend to find unsolicited redesigns as not contributing a lot to the conversation. They aren’t aware of the constraints that the original team was working under, and they’re probably not doing a lot of really targeted user research and generating a lot of insight based off of what the user base is looking to have help with solving. When someone comes up with a prettier boarding ticket for an airplane, it tends to not rock my world.

I try to be really mindful of that when I create the teardowns. I’m not going in and saying, “No, no, no, I don’t agree with this, or my opinion is better”. It’s much more, “According to my own experience going through this as a user, I encountered some areas that might be confusing or generate anxiety”. Any time I’m pointing out the “bad” I try to do so with the unspoken caveat I’m someone who’s going through this product on my own, I’m not aware of what kind of conversion metrics they’re working with, where people are being lost the most or not, what’s most relevant to the people who are the core user base, etc. I try to keep things light and respectful.

As far as actually receiving push back from the companies that I’ve actually worked with, I anticipated that to a degree when I started. I picked a company called LessAccounting because I hadn’t used their product before. I wanted to go through one where I hadn’t worked with the company in any kind of professional way and hadn’t been a user myself. I posted the first teardown to Slideshare and didn’t really think a lot of it. The next morning I woke up and received an email from one of the founders. I was sitting in my inbox and I was like, “Oh no.” I was pretty sure it was going be like, “Hey, thanks a lot for passing it by us and by the way you’ll be hearing from our lawyers. Consider this a cease and desist.”

I very trepidatiously opened the email and it couldn’t have been more opposite. They said, “Thank you so much for making this. We’ve already made some of the changes that you recommended, this morning. It looks like you’re writing a book. How can we help promote it?” They wound up featuring it on their blog.

It was something where I thought, “I should probably do more of these,” and to be 100% truthful, I figured at some point I would get a negative response from the companies I featured on the site. To this day I haven’t gotten a single one. It’s actually led to some really positive relationships, and I’m really, really thankful for that.