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From conversion to retention: industry experts on improving your onboarding

If your product is to survive and your business is to grow, improving your user onboarding must always be top of mind.

There are two key reasons for this. First, onboarding is the one thing that every user of your product experiences. Secondly, your onboarding strategy must adapt over time as your product and business evolve.

From converting trial users into customers, to helping those new customers find their “aha” moment with your product, to keeping them coming back to experience it again and again, we’ve been fortunate to host some of the brightest minds in this space join our podcast to discuss this fascinating field. This week, we’re revisiting an episode that features some of their sharpest insights to help you take stock of and improve your own onboarding. You’ll hear from:

To hear each of these conversations in full, check out episodes of our podcast linked in each subhed below. You can also subscribe to the show on iTunes or grab the RSS feed in your player of choice.

Samuel Hulick on making users successful

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

Samuel Hulick: 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.vation

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.

It’s a matter of building up habits in people’s lives.

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.

Geoffrey: What do you look for in high quality onboarding?

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.

Casey Winters on how to measure onboarding success

Casey Winters
Adam Risman: You’ve got two measures for deciding how to focus on onboarding. One is the frequency target, and the other one is the key action. How does a startup, particularly when you have users who derive value in different ways from a product, go about pinpointing what those should be?

Casey Winters: For frequency, I always try to figure answer, “What is the offline analog to this product?” For Grubhub it was calling a restaurant on the phone and ordering food. We researched how often people did that. People were doing it once or twice a month on average. So, we decided our frequency target, at first, should be monthly. For Pinterest, it was very similar. What is the offline action that Pinterest is replacing? The closest thing is browsing a magazine, which are monthly subscriptions. So, it’s probably a monthly thing here.

Long term, you want to increase the consumption from whatever the offline analog is, but to start you want to understand what the baseline is that you’re trying to replace. That can be an online product as well, but in those two cases we were really trying to replace what people were doing offline.

The key action is a little harder. What is something someone does in your product that indicates they receive value? For Grubhub that’s pretty easy. They have to transact to get value, so that’s the key metric. For Pinterest, it was a little bit harder. There are multiple ways that people can get value. They can just browse a bunch of images and think that’s valuable. They can save things, and find if they save something, we showed them something valuable to them. Or, they can click to the source of the content. We looked at those three things.

Read more here about how Casey defines successful onboarding.

Clicks can be gained by clickbait. It’s hard to understand if people are scrolling through a lot of images because they like seeing them all, or if it’s cause they can’t find what they want, so they continue going. So re-pin, the save functionality, was the easiest to understand that the person definitely is receiving value. And it correlated the best with long-term retention.

Then you have to test that hypothesis. If you push people toward saving things, do they actually retain better? Our first experiment was forcing everyone to re-pin. That did not work. The second set of experiments was around educating people on how to re-pin, and the value of a re-pin, and that did actually increase the activation and retention for the business.

Adam: With a discovery tool like Pinterest, or a productivity tool like Trello, you have to paint a picture for people of how to use the product, so they’re not just staring at a blank page, wondering what to do next, and then leave and never come back. How do you strike a balance between showing people value as quickly as possible, but then also not creating so many steps that it weighs the user down, and you lose them along the way?

My basic philosophy here is that you want to get the person to product value as fast as possible, but not faster. What I mean by that is if you need to understand something about the person to be able to show them value, ask for that, but don’t ask for a ton of things that you may not use, before you show them the product. Then they might drop off the product before they even see what the real product is.


For Pinterest, we need to know what you’re interested in to be able to show you value, because the goal of the product is to show you things that you’re interested in and then get you to do those things in real life. First, we asked you to follow people that share your interests, and then you would see what things they’re pinning. Eventually we switched to, “What topics do you care about? We’ll show you the best content in those topics.” That worked pretty well. Pinterest is always seeing if there’s a better way to do that, to connect people to the value even faster.

We tried things where it’s like, “You picked that topic? Here are a bunch of subtopics. Pick from these.” That added too much friction to getting to the value. We tried going deeper, but it was too much friction and it didn’t work.

For Grubhub, it didn’t need onboarding at all. You search, you see a bunch of menus. It’s pretty clear. There’s basically no education at all. You just go. If you have a product like that, that’s great. You can skip this entire part of the funnel. But for Pinterest, it was the most important part of growing the business.

Adam: I imagine, as you’re signing up for products yourself, you’re probably evaluating these experiences. Is there anything you see over and over, and think, “Why do product companies keep doing this?”

Casey: The most common problem I see is that I sign up for a product and it just dumps me into something that’s empty, and I have no idea what to do. The empty state, or the cold start, is a huge problem. I feel like I’m an expert in this, and I don’t know what to do. How is the average user going to know what to do here?

The other thing that unnerves me is when I get a book to read in front of the product. I just want to get into the product, and have you contextually educate me on what I need to care about at this particular moment, not tell me in 10 screens, which, by the way, most people are skipping through as fast as possible. I prefer the in-product, contextual education more than a user manual before I even see the product.

Scott Belsky on crafting your product’s first mile

Scott Belsky










Geoffrey: Who is really nailing this first mile right now?


Joanna Wiebe on testing your onboarding messaging

Joanna Wiebe
Joanna Wiebe: A one-to-one email often goes over far better than a business-to-many, or a business-to-one email. If it’s Wistia sending an email, versus Chris at Wistia, that’s an interesting test. Test that versus just Wistia sending that email. Or test a Success Manager against the company.

Writing it in the narrative style is another thing, where you open with a hook. Treating every email like it’s a mini sales letter. We did this with Wistia, and I wrote about it on the Copy Hackers’ blog. We tested eight onboarding emails. They have three sequences that are triggered based on different activities that you do, and we worked on the third trigger sequence. This whole sequence comes at the end of the trial in most cases, and it’s where you’re trying to move people from trial user to paying customer. Those are my favorite places to optimize. They’re usually a good way to get a real read on whether what you’re doing is going to move people or not. Because at the end of the day, they either give you a credit card, or they don’t give you your credit card. Then you can learn something real.

We tested these eight emails against their control. All we did was a basic rewrite. It’s like what a lot of copywriters would do when they go in for their first day. It’s like, “Well we don’t know what to do with you yet, so just go like rewrite these emails.” It was an exercise anybody could do right now, where you sit down, you assess the emails, and then basically rewrite them with different strategies, like using problem agitate solution or a framework like that.

We kept the message largely the same, but we just changed the way that message was being expressed. Seven of the eight emails we tested were two to five times as long as the control. So we had longer copy, but long doesn’t work just because it’s long. It works when you actually say things that make people feel something and draw them in. You have to allow yourself to use more words, which was very uncomfortable for the Wistia team, understandably.

wistia onboarding email

So we tested these eight emails. They were longer, and we removed the videos from them in most cases. Wistia is a video company, so that was uncomfortable for them. We ran the tests, our eight emails against their eight emails, and ours brought in 3.5 times the paid conversion. And it was just a rewrite, right?

I’m talking to them in their language. I want to use real specifics.

It’s really just looking at your copy and saying okay, people are actually going to read this. People are busy, but they’re going to take the time to open this email. I want to make sure that I’m hooking them. I want to make sure they know I’m talking to them in their language. I want to use real specifics. And when it comes time for me to actually sell, because these emails at some point in the sequence have to sell, I want to make sure that we are really zeroing in on a pain, and then expressing how Wistia is the solution.

The copy rewrite came from really listening to what their customers were saying, going on Amazon and doing review mining. Founder Chris Savage did a podcast, and he talked about YouTube. It was early in Wistia’s time when like people were still thinking, “Why wouldn’t I just use YouTube?”. He said something about how you expose your video to a world of crass strangers. I thought that was interesting. It turned into the headline for one of the sales emails.

It was something like, “What’s red and unsupported and stuck in the middle of a bunch of crass strangers?” The answer was, “Your videos on YouTube”. It was setting it up with this fun sort of joke framework, what’s red and white and whatever all over.

You’re still playing with something that doesn’t feel angry or offensive or defensive. We are saying Wistia is better than YouTube, but we’re saying that in a friendly way that is actually still about getting into the problem with YouTube for businesses.

Shaun Clowes on balancing retention with activation

Shaun Clowes
Adam Risman: I know a lot of organizations are tempted to focus on acquisition, but you really believe that you have to solve the retention problem first. Why?

Shaun Clowes: It never ceases to amaze me how much time we as a industry spend optimizing our acquisition tactics to acquire a huge bunch of people. When you think about all the energy that has gone into this, and understanding who those people are and how to go and find them, and then you look at the number of people that drop off in the first five to ten minutes, the first day, it always breaks my heart. Even at Atlassian, where I felt like we were getting better and better at this, we had the charts that would show us what was happening. Every one of those people is a person whom you have fundamentally burnt. You have failed to give them what you told them you would give them.

When I think about the ROI of things that you can do in a business, make certain that your customer is safely handed from acquisition to the activation. Make certain that they are activated and you have done everything in your power in order to make certain they have found their “Aha” moment and they have began habit forming. Then make certain that they’re getting the maximum value from your software though engagement. Those are generally very low investment, but with potentially massive rewards. Not only because you keep those users, but if you truly succeed at that, and you get high engagement, then what you really get is sustainable businesses, because you get word of mouth.

People who are highly engaged with your software are always the people who love it, and those people who love it will tell other people. The most authentic form of acquisition, by far, all day, every day, is word of mouth. It’s amazing the business you can build once you have that engine going.

Adam: I know you can’t prescribe tactics without knowing anyone’s business, but where is the low-hanging fruit when it comes to retention strategy?

Shaun: When it comes to retention, again, I would emphasize having an understanding of what your view is at your activation loop. Your problem is almost always going to be in activation first. If you have $100 and you’re starting up, I’d bet $80 of it in the activation phase, because what happens is people fail to have their “aha” moment. And even if they have their “aha” moment, they can drop out before it becomes a habit. There’s a huge amount of value there.


The tactics I use in that space are first understanding what my drop off rates are, and then watching users in their very first experience. I try to understand, “What are the buttons they don’t find? What are the things they are confused about?” Then try really simple stuff like a dialogue box saying, “These are things you are probably looking for.” Lead them in the most likely three places they want to go. It’s amazing.

At one point we had a 12 step onboarding flow at Atlassian. It was deeply involved, it had a whole bunch of things that it taught you, and it was very successful. But when I talk about champion/challenger, we were constantly trying to beat that, and we later on ended up with an onboarding flow called “Choose your own adventure”. It was one dialogue box with three buttons, and it outperformed the 12 step program. The 12 program was trying to tell you enough that you could do the rest, but it turns out that most people arriving at the software wanted to do one of three things. Rather than needing to educate them about those three things, about the way in which they could go about thinking about the software and find it, just giving it to them was enough.

Adam: Do you feel that startups ever underestimate the depreciation of onboarding? Because it’s one thing to get it humming, but context is always changing.

Shaun: You’ve straight up hit on one of my favorite topics on this. For example, I look at an activation program as a never-ending stream of work. It’s fundamentally a champion/challenger problem. It’s not, “We will solve it, we will ship it and we will be done.” We ran hundreds of experiments in activation in Atlassian and the vast majority of them failed, but the ones that succeeded did so in such a massive, metric-moving way that, for the investment versus the reward, it was incredible.

There were times when we shipped an onboarding flow, and wondered if it was the best we could do. My argument was always that we’ll never know until we continue mining it. The answer was we always did better. We always managed to do better.

The second reason you clearly must keep doing this, is that your brand promise keeps changing. The features that you deliver to the market change, and if your onboarding is static, then, again, you will fail to meet your promise. Plus, your product itself changes. The way image information architecture exists, it’s just this constant program of work to make certain that you are safely delivering those users from the marketing site into the product, and then from their first touch of the product to getting their value, and from getting their value to forming a habit, and from a habit into high engagement. It’s that simple.

Intercom on Onboarding