Onboarding UX with Pulkit Agrawal of Chameleon

Onboarding is a customer’s first impression of your product. The way you research, design, and implement user onboarding can make or break the overall experience. So how do you refine this important aspect of your product’s UX? 

Pulkit Agrawal, Co-founder and CEO of Chameleon, joins us to discuss just that: How to optimize the user onboarding experience to get your customers off to a great start. 

In this episode:

  • What is onboarding?
  • Best practices for onboarding users
  • How to integrate personality into onboarding

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Listen to the episode


  • [1:24] What is onboarding in an app?
  • [3:50] Measuring the onboarding trade-offs
  • [6:24] Where should UXers start optimizing their onboarding?
  • [8:42] Limited segmentation in onboarding
  • [12:09] How can UXRs understand the customer’s core issues?
  • [15:06] Onboarding golden practices
  • [18:01] Great onboarding examples
  • [22:40] Increasing user motivation
  • [26:55] Implementing the right triggers and motivations to match the user and the product
  • [28:49] Onboarding mistakes UXers make
  • [30:38] The big picture versus the details
  • [33:06] Top tips and takeaways about onboarding

Sources mentioned in the episode:

About our guest

Pulkit Agrawal is the Co-founder and CEO of Chameleon, a product adoption platform for SaaS that helps companies create better user onboarding. He is also an Angel Investor at product-led startups and a part-time featured speaker at Product School. Before founding Chameleon, Pulkit was the UX and User Onboarding Mentor at 500 Startups.


Pulkit Agrawal: Let’s say you deploy a new brand, new feature. There should be a consideration of how are we going to onboard people to this new feature? Or you make a UX change—how are we going to onboard people to that? I think it does extend, and I think some of the principles around user onboarding are very effective for a bunch of conversion funnels in the product, or loops in the product. However, we think about them.

Erin May: This is Erin May.

John Henry Forster: I’m John Henry Forster, and this is Awkward Silence.

Erin: Silences. [laughs] Hello everybody. Welcome back to Awkward Silences. Today we’re here with our guest live from a wedding in the middle of a wedding, but Pulkit Agrawal, who is the co-founder and CEO of Chameleon. We’re going to be talking about onboarding flows and how to design really good ones using user research to do so. Thank you so much for being our guest today.

Pulkit: Really great to be here. Thanks for having me. Awesome.

Erin: We got JH here too.

JH: Appreciate you joining us. I’m excited to learn about onboarding, get onboarded-to-onboarding. I suppose.

Erin: We’re so happy to have you here live from your wedding again. We’re going to be talking about user onboarding and which I know JH is excited about. We’ve been thinking about, we’re always thinking about onboarding. We have an app, so we want to make the onboarding experience good. Maybe we can learn a thing or two from you today, but let’s jump right in when you talk about onboarding, maybe it’s obvious, but what are we talking about? What is onboarding in an app? What’s that? When does it end? When does it start? What is it?

Pulkit: Yes, good question. It’s actually probably less obvious than it. Maybe it seems so typically most people consider onboarding as post sign-up until activation. It’s really the user’s first experience with the product. It typically goes to whatever you define as the activation point or activation metric. That metric is something that typically helps determine someone finding first value or achieving the first objective in the product and then they can explore further.

I think there’s a little bit more nuance to it. One is that the onboarding, I think really begins from the first impressions somebody has of your product. Now, those impressions might be pre-sign up. When they’re visiting your website or when, for example, they come in through an ad, they have a different context and understanding of your product than somebody who maybe comes through word of mouth.

That is important and necessary context as you then treat that user post signup because they may have different expectations, different intentions. Whether or not the pre-sign-up part of it is technically onboarding or not. It definitely has an impact on onboarding and should be considered. Also, I’d say the other end of it’s a bit of a gray area because a user is likely to have many what we call aha moments points, where they realize value.

Something suddenly makes sense. It’s like, oh, I get what this is about. They’re likely to have many of these in their journey. You might have some smaller act moments of activation or delight that help propel a user to the next stage. Even if they’ve done their first major activation moment, they may still have other features to discover and learn about that might be either more relevant for them or might cause stickiness.

We’d like to think of it as it’s really the first time someone gets value from a part of a product. Now that could be just the overall product, but it could be on a feature level. Actually, you should be thinking about user onboarding for each feature. Let’s say you deploy new brand new feature. There should be a consideration of what, how are we going to onboard people to this new feature? You make a UX change?

How are we going to onboard people to that? I think it does extend, and I think some of the principles around user onboarding are very, very effective for a bunch of conversion funnels in the product, or loops in the product. However, you think about them.

Erin: As I was just saying, with onboarding as you were describing it, there’s potentially a lot of trade-offs when you think about everyone wants to avoid friction, but some friction is good. Some is necessary. We need to create friction so we can authenticate you so we can segment you and send you on the right journey in your onboarding to understand what your job is to be done.

I’m curious how you think about measuring some of those trade-offs. If you want to do, say., some AB testing or usability testing of your various onboarding.

Pulkit: Good question. In the end, it’s going to be about what’s the driver for the value for the business. Let’s say your driver for value is that someone makes a purchase decision or is joins a subscription, or it’s how much content they consume, et cetera. Based on how– You’re willing to work backwards from that, which is okay, well this is, we want to drive long-term success.

Presumably, it’s like retention or it’s some engagement metric. We will want to see through the different onboarding flows, what helps people get to ideally the leading indicators for those things. Obviously let’s say we want people to make these, take these key actions. People take these key actions. We know they’re going to stick around, or it correlates or causes people to stick around if they take these key actions.

During the early parts of the product experience want them to take those key actions. When we AB test with friction, more friction, or less friction, we can ideally test for conversion to those key actions. Now I think if you’re beg- if you’re starting out and you’re like, okay, I’ve got this one flow, should I add more friction or should I reduce friction? If you’re trying to think about that, the goal really is, are you finding enough people that are– If you’re not finding enough people that are getting to that action, you can reduce the friction.

It’s probably a good place to start. It’s like, okay, let’s reduce the friction to get more people in. If you’re finding that people are getting pretty far into your product, but are not sticking around. You find that they’re not high-quality users or it’s the wrong type of user that isn’t driving value. That’s when you might want to think about adding more friction because what you’re trying to do is increase quality versus quantity.

Normally I think most teams aren’t at the point where they’re having that problem. If you’re a super early stage, you probably have a lot of friction. It’s fine because it’s like, okay, let’s do concierge onboarding because what we want to do is find the high quality we want to find product market fit for a very small niche group of people. Then, but as you’re midmarket or as you’re scaling, then most of the problem shifts to, okay, well how do we drive more quantity because we’ve already identified the right group of people.

JH: That makes sense. Something you said in there I’m curious is if the team’s like, all right, well let’s start optimizing our onboarding. Where do they actually start? Is the first thing doing some discovery or research around what are the critical actions to get people to first? Is it we think we know those? It’s okay to have some hypotheses and some guesses there. Let’s figure out some different ways of getting them to those things. Where do you recommend teams start?

Pulkit: Good question. There’s lots of places that can begin. I think couple things that think about one is if we think about the funnel from the start of the product to the end of the product or the start of the user journey to the end of the user journey, I would recommend you start towards the end. You’ve already got people as far along as they were going and you want to get them further along.

So if, for example, people are activating, but not buying, then I’d worry about that. If you think that people are buying, then you’d worry about activation. If they’re activating, then you’d worry about sign up or so I would work backwards, rather than forwards when you’ve got a place in the funnel that you think I want to fix. It’s like, okay, well, let’s because from onboarding activation is a problem.

We want to improve activation. Again, apply the same principles where in the activation journey are people falling down. With that, you should ideally get to some very specific narrow flows in the product. People are really struggling to go from step one or step three to step four. Rather than generally being like, okay, we have an onboarding problem.

The more you can narrow it down, the lower risk you have when you’re finding solutions, once you’ve got to the phase that you want to solve, then you want to hypothesize what is the friction what’s preventing them getting across this gap or this chasm or whatever it is in that you can go and do some user research or you can go and ask them, or you can add hypothesis based on your intuition or what you’ve learned from your support or sales teams.

Then once you have the clear hypothesis of these are the friction points, then you have to come up with some potential solutions. Those are then ones you can test and validate. Now you can validate many ways. Again, you can validate a prototype or you can AB test and validate in real life or you can see tests and you don’t even have to AB test if you don’t have enough scale.

I think to recap, find the place where you’re confident is the problem. Then try to understand what is the actual problem. Why are people failing? Maybe they’re experiencing some friction. Maybe we haven’t communicated the value upfront and they’re not motivated. Once you know, or have a good sense of friction, then you apply potential solutions and then validate those solutions.

Erin: You talked a little bit about the segmentation of whether it’s by right company type or user persona job to be done, whatever it is. Do you recommend most companies start with limited segmentation? How do they go about that process of right. You imagine a classic funnel, whether it’s the pirate metrics, whatever it is of I’m going to sign up, I’m going to have an aha moment.

I’m going to activate, I’m going to pay some money. I’m going to pay more money and, and so on and so forth. That’s flat and everyone has the same journey. At some point you need to say those steps are actually a little bit different somewhere in there for different kinds of people. I’m curious how you’ve worked either, in your own companies or with other companies to figure out what are those meaningful segments to think of onboarding differently, across different kinds of people.

Pulkit: That’s a really good question. I think most companies probably don’t do a very good job of this, which is that they don’t make difficult decisions about personas and who the personas are and what the people are doing. I’ve spoken to so many companies and they don’t even necessarily know exactly what users are looking for when they first sign up or go in.

I think that most software teams will find that there’s multiple use cases or people looking for different things. I think it’s very important to ask those questions in either the signup flow or soon afterwards, and it can be if you have no idea, start with a free form question, what are you looking to do? And hopefully you’ll get some information that will help you be able to narrow down specific use cases, and you can then structure the round two of that question to be like, which of these four things do you care about the most? And then you’ve got structured data.

Once you have structured data, then you can start to use that to show diff segment and show different experiences. It could be different email campaigns in product campaigns. It could be different offerings around talking to sales or talking to CS or plans or whatever else. There’s a really good case study that superhuman, the email client wrote up and they said that they were had decent product market fit and they were confused. They’re like, some people seem to be strong advocates or user power users, but some people don’t.

We’ve got mixed product market fit. What they did is they did this product market fit survey. It’s a survey. I think that Sean Ellis popularized, very simple question. How disappointed would you be if this product went away, give you three options, not very somewhat, very disappointed. The idea is that if you have at least 40% of people saying very disappointed, then you have some level of product market fit.

Anyway, superhuman did this micros survey and they asked everyone about this question. What the interesting thing was, they also had characteristics about each user attached to this survey. They knew the role of each user when they’re answering this question, and so when they did the analysis on this, they realized that actually founders and CEOs or executives had extremely strong product market fit, but some of the other job titles did not.

Then they oriented their product and their use cases, their messaging, their onboarding around that use case, which already had strong product product market fit. They wanted to expand that. I think companies with pretty low effort can start to explore, understand like what are my personas? And then once you have some of that structured data, you can ask them the question or you can collect it at some point.

Once you have that structured data, then you can do a lot of analysis based on that dating like, what is retention for this by role or what is retention by company size? And then you can start to understand what the different patterns are, and that will help you narrow and focus on where you need to optimize and where you need to focus.

JH: Nice. Another thing that you’re saying I’m imagining maybe people don’t do enough of, cause you’re describing that with the segmentation the personas, is it feels like a space where there’s so much like written about onboarding and so much that’s shared that people probably get pretty drawn to the solution side pretty quickly of like, oh, we should use this like tool tip tour, or we should do this wizard thing or whatever. I’m just imagining that there’s probably like a foundational step of research that’s pretty important to go actually here.

Like where are your current users hitting points of friction or getting stuck or losing motivation. We spoke so recently who has a user base that’s lower tech savviness. They found that the two factor step was like really confusing to them. That felt like a key onboarding insight. I’m just wondering like, how do people get the right balance here of like jumping into prototypes and like, mimicking stuff they see in other apps or see case studies about versus like going to actually understand the core issues that are facing their users.

Pulkit: I could relate with a personal experience here, which is when, so comedian my company helps teams build tool tips or onboarding wizards as you called them guides, et cetera. What we found was that a lot of people were building things that would not that good they just didn’t look good. They didn’t work well. Remember, at some webinar we did, I asked the question, I said, just anecdotally, how many people dismiss the welcome tour on the first step and an astounding 91% of people said they did.

I was like, wow, so all of you folks are interested in building these because you’re the audience, and yet you dismiss these what’s going on. There’s clearly a massive disconnect. That disconnect is often people are building these, as you said, very solution oriented, but also from their perspective, they’re like, oh, Hey, people aren’t succeeding. We show them our product. We show them everything in our product. We need to show them.

They’re just throwing paint against the world, guessing that, oh, something will stick like, oh, one of these things will be helpful, but actually most people don’t want to go into your product so that they can learn your product. That’s not their goal they’re going is to meet some need or complete a job. Actually, we as a company introduced micro-surveys as a product line because we realized we needed to help our customers learn and research more than they were doing to help them build more effective onboarding experiences.

With micro-surveys, which is single step questions in the inside of the product targeted at the right user triggered at the right time, in the right place, based on what the user has or hasn’t done, that is really important to know what to then build and coach and guide people on, because that way you’re not throwing paint against the wall, but you can really assess, like people are struggling at, because of this terminology or they’re looking to do something, we didn’t even realize that.

Another way, of course, we encourage people to collect folks to do interviews through that channel or do more user interviews to really understand what the problems are before they go and try to solve them. Very much aligned. If you feel like your onboarding isn’t working or you’ve tried doing some onboarding and you feel like it hasn’t had the lift you expected most likely you need to do a bit more research or a bit more under get digging into the user mindset to help you build the right one.

JH: Just build off that quickly. Are there things for this type of research that are like particularly effective I’d imagine, like seeing somebody go through onboarding the first time when they truly want to use the app would seems like maybe the gold standard talking to somebody right after they go through it maybe is pretty good too, or grabbing somebody who’s maybe close enough to your target user and then making them go through it, in a more contrived exercise, what are the best ways to get the right signal on where people get stuck on that? Because I just imagine if you talk to somebody you on-boarded three weeks ago, they can’t even really probably remember some of those things.

Pulkit: Generally we’ve become really good at shipping product quickly, but we haven’t been that good at like being lean about research and continuous research unfortunately, or continuous discovery, tourist, Tara talks about, isn’t become as commonplace as I think it should have. I think catching people in the moment is really valuable. For example, they’re trying to learn a new feature and they U-turn, they go back or they rage click or they do something else or they’re just like filling stuff out and they get to some key moment asking and prompting then for them to answer a simple question or book a call to do some feedback is valuable.

The more we can do it in the moment, the more effective it’ll be. I think if it’s restricted as simple, short, convenient users are far more likely to engage, we’ve seen that on average across our Microsoft is, we see millions of end users a month. The average response rates are 50% to 60%, which is incredibly high compared to email surveys where you get two to 3% click through and then you get 40% conversion on that email survey.

It’s multi-question because people are like, they’re not in the context anymore. I think the more you can do to grab people in context and if you can ask them a question that they can connect the dots on why you’re asking that question, they’re far more inclined to respond to you because they say, I’m checking out the dashboard page and you’re asking me a question about the dashboard.

I can connect the dots. The stuff that I tell you might actually be helpful to me on the dashboard because you’re make an improvement here. It’s much more beneficial and the user can see the value of that. They’re much more likely to respond. The more we can do to catch people in the moment is definitely going to be better and more accurate.

JH: All right, a quick awkward interruption here. It’s fun to talk about user research, but it’s really fun is doing user research and we want to help you with that.

Erin: We want to help you so much that we have created a special place it’s called userinterviews.com/awkward for you to get your first three participants free.

JH: We all know we should be talking to users more. We’ve went ahead and removed as many barriers as possible. It’s going to be easy. It’s going to be quick. You’re going to love it, so get over there and check it out.

Erin: Then when you’re done with that, go on over to your favorite podcasting app and leave us review please. I know you’ve worked with lots of companies who are focused on onboarding, and I’m curious if you could talk to us about either some specific companies or what companies have in common that are doing onboarding well. We’ve been talking about onboarding in general in terms of what do you want your users to accomplish and how might you go about researching what that looks like.

What are some exemplary, if not this here’s a tour of all the features in our product and check the boxes and experience all of them. If that’s not a great way to do it, what does it look like to do it well?

Pulkit: Good question. I think if we want to look at the folks that set the standards, we have to look at games. They are incredibly effective because they are super complex, lots of pathways, lots of new things to learn, and so they have to onboard. I think I’m not the original person for this example, but Super Mario everyone is pretty familiar with. When you first start, you have Mario on a wall and the only way to go is right and there’s nothing else you can do.

You go, and then there’s this brick that appears in the air and you’re like, what is this? What can I jump? And then you jump and then can I go above it? And can I go below it? And so you layer in the learning and you give people value. You hit the break and you get a coin. You’re like, oh cool. This is cool. I’ll do this again. There’s reward there, and it ties into the psychology, Neal’s hooked model, which says like, there needs to be a trigger and then there needs to be an action.

Then there needs to be a reward and then there needs to be work done. You ask people to do work after you give them the reward and that will creates this like the habit loop. I think that can be a good example, obviously software, if we’re thinking SaaS or others is maybe not easy to be completely parallel to that. If we think about good principles, it’s start with very clear sign posting and have people accomplish things and then reward them. If you reward them and then ask them to do more work, then they’ll likely do it.

If we want to visualize this, I think some companies, I’ll talk about ones that everyone can nod their head to, Slack is a really good one and Slack does two things. One is that Slack bot which we can part because not every company has a Slack bot or a bot type of conversation feature. Let’s ignore that part of it. The rest of it is actually really good as well.

Some components of the rest of it, I’ll talk about one is that when you’re first loading or when you’re first cutting into it it actually de focuses a bunch of stuff. It doesn’t show you everything at once. It takes you to one thing like let’s learn the one thing. It’s almost like hiding menus or hiding options. As companies think about empty states, think about does everyone need to see everything or can we just keep it the scope smaller so people know where to go.

The other thing Slack does well is that when it does give its onboarding, it’s not so intrusive that you have to choose. Do I want to take this onboarding now or not? You can be like, I’ll take it later or it maybe appears as a banner at the bottom of the page. It gives you a chance to opt-in because when people are going and trying new products or features for the first time, there’s excitement, there’s motivation.

They want to learn and discover. If you bat that away and say, actually first read my manual, this 10-step talk before you get started it’s really demotivating. Frankly is sad. Don’t always get in the way, just give people the chance to opt-in if they need help. Often what people find is when they’ll click around then they’ll like “Oh, actually now I realize I need some help and I want to go look for it.”

That’s why so don’t be too intrusive. Give people the option to opt-in and take it again later or come back to it. The other thing that Slack does really well is that its onboarding is very bright. It’s like there’s a bright blue banner. There’s a bright green tooltip. What it does is it brings confidence and interest into those elements and components. Too often I see really drab looking in product experiences or really clunky JavaScript tooltips that are white background or white app and people are missing them and the habor doesn’t look good. It’s feels like you’ve built this because you think you shouldn’t be building this.

You’re embarrassed and defensive and it’s come out as not a very good user experience. Whereas if you look at the Slack example’s like, “Hey we’re confident. You need to know something with this thing that we’re going to show you so value.” We want to draw your attention to it, check it out. Then if you’re not interested, that’s okay. I think if companies frame it as like, “Hey the stuff we’re going to show you is going to be super valuable.” You’re going to enjoy it and appreciate it.

Let us be confident about putting in front of you. Then I think it aligns the user’s expectations are much better. Those are maybe three small things I could go on and on about all the good practices. If you want me to, I will around user onboarding but maybe something.

JH: I have one that maybe will stir some other examples to mind as we can keep hearing your knowledge is we’ve talked about this equation of the motivation needs to exceed the friction or the challenges they face in the process. I think my mind, and I imagine others quickly goes to what can we do to reduce friction. Are there things you can do on the other side to increase motivation, like get people more excited and then solve it that way?

Pulkit: It’s almost like I’ve seated these questions. I love these questions. I haven’t. I’ll go back to, there’s a professor of persuasive technology called BJ Fogg at Stanford. He talks about this being two accesses I guess. One is to drive action, to drive human behavior change or just actions in people. The Y-axis is motivation, the X-axis is ability. When you have sufficient motivation and ability, then a trigger creates action.

You have to still have a trigger. If we think about that from the software perspective, what does motivation line up with? It lines up with value proposition are people clear or it could be motivation but just are you explaining your value clearly enough and then ability lines up closely to interface. How easy is the adjective to do the thing you’re trying to do? Then the triggers can be prompts that you do in product or out of product.

It’s absolutely important to drive up motivation and you shouldn’t just rely on improving ability, improving UX, making things “more intuitive” which is often something that I hear from people who may be as a challenge to having any kind of onboarding, they’re like, “We just need to make the product more intuitive.” There’s two challenges to that.

One is that if they’ve experienced something that you’re showing them before, then you can make it intuitive but as soon as you’re teaching something new, whether it’s the new way of doing something, whether it’s a new technology, a new tab, there’s going to be teaching involved. If there’s teaching involved, you can either have that teaching live ever present in your interface or you can show it through a dynamic experience.

You don’t need to teach everything forever, you can teach it once and people will learn. I think there does need to be some prompts and triggers but motivation is really important to drive up. A couple of other points on this which I’ll cover, a lot of users end up not spending very much time on marketing websites. Back in the day, like 10 years ago marketing websites was where you conveyed the value of the product.

Then you would either request a demo or you’d sign up and then you’d go into the product and then you were in the I’m doing it now, I’m using the product. Over time people have spent less time on marketing websites. It’s gotten easy to sign up for products. Everything has an evaluation phase or a trial. People are landing in products without really rocking the value or knowing the full value proposition.

Actually teams should be doing a lot more marketing or product marketing in the first user experience to reemphasize the value of the product or the use cases. Sometimes customers will ask me, “Hey, what kind of video should I show as a first experience?” I tell them, don’t show a video of your product, show a video of your CEO talking to the user about why you built the product in the first place.

That’s the kind of engagement that people want because they’re still assessing is this something of value. Flow all of the great content you’ve created on your website for your users who are prospects. There’s still prospects in their first user experience often. Make sure find ways of bringing that in. One way that we are doing that is empty states where every empty state has almost like a landing page component so that when you go into a product there is a call out where instead of the product fun UX, there’s the call out with the value proposition with a descriptive graphic, a CTA.

That’s one example of doing it but really highly recommend it. If you remember the old days of Snapchat, I don’t know if you remember that but it was a very difficult to use product. It was very confusing. The navigation was like, “I don’t know where I’m going.” It got really strong adoption because it had a really strong value proposition and people were very motivated to use it.

That’s just an example, you don’t necessarily need to only optimize the UX or the ease of use. If you can establish motivation and value prop for users, they’ll get really far and they’ll figure the stuff out themselves.

Erin: Yes. It’s really interesting, especially the founder video, and bringing the product marketing into the apps little counterintuitive. I think that’s really interesting. As you were talking about the Mario Brothers’ example on how games have done such a great job of doing onboarding well. I immediately started to think about gamification of everything. It’s tired in a way. It’s like, oh, let’s gamify this, and not every user wants badges and rewards and app for doing whatever things are doing.

I’m curious getting that tone right in terms of keeping your users motivated. I imagine that looks different depending on your user base, the kind of app you are, the kind of value you’re providing. I’m imagining an accounting app and you’re just like throwing cartoons and trophies and they’re like, “What the hell is this?” Yes curious about how you match, how you implement triggers and these motivations to match with the user in the product.

Pulkit: Yes. It’s a good question. I think heuristic for this is like is it gimmicky or is it true? Is it truly helpful to somebody for to know this or to think about it in this way or is it just a gimmick? I think if you are truly aligned to, I’m going to provide value to the user and this is going to make it easier for them to succeed, then I think you’ll have a different perspective than like, “Hey, I’m just trying to drive my metric up and I’ll throw whatever I can to drive my metric up.”

Gamification there’s probably been a reversal against gamification because we’ve over-indexed on it. I think if we think of the accounting app something that could work is a checklist of things that people need to complete or a progress bar of like, “Hey, these are the stages that you need to get through.” That could be called gamification, or it could be just a UX pattern that will help someone understand where they are in the journey and what else they need to do.

I think finding the right balance and tone absolutely necessary but yes being true at heart, what am I trying to accomplish? Am I really trying to help this user get value out of my product or am I just doing it for eyeballs or something?

JH: What are things maybe that people aren’t doing well when it comes to researching onboarding? Let’s assume they’re trying to do some amount of research and they are trying to catch people who either just onboarded or in those moments, but are people maybe not asking about things that they should be, or are there certain techniques that they should be considering. From your experience, what maybe are people missing or not getting right in this area?

Pulkit: I think one of the biggest things people aren’t getting right is the continual research. They’ll often be a big project to improve user onboarding and that’s the time where everyone will do a lot of research and go and speak to users and there’ll be a lot of design iterations and then they’ll build it and then they’ll dust their hands and like, “Okay, we’re done.”

We’re not going to touch this again for nine months because it’s tiring. It’s a big project and you’ve spent a lot of time and effort and it’s hard to get users into a room and talk to them, et cetera. What then happens is that you put a good foot forward from the design phase but you don’t iterate on it quickly enough. I think as we know, talking about people getting into products really easily and quickly, well the product and first user experience need to iterate a bit like website so iterate it which is like lots of conversion experiments all the time running and a lot of testing.

That’s what it should really look like. A lot of that should be continual research over time. I think the other thing that can be easy to miss is that the context changes over time for even the same type of user for Chameleon. When we first started working on Chameleon, we had to answer the question, why a tool for this? Why wouldn’t I build it in house but the same user persona now asks why comedian versus why something else?

It’s of course we’re going to use something. It’s just which one. That context has changed quite a bit and so our positioning, our messaging, what we highlight in the product is very different. I think that’s also important to realize is that’s why it’s important to keep changing and adjusting your onboarding.

JH: That’s a great example. Maybe a different question that’s in the spirit is just from stuff I’ve seen and read and been privy to on Twitter and elsewhere. I feel like you see both macro and micro examples of big onboarding changes or wins. What by that is sometimes you’ll see people talk about how they really overhauled something. We took this dense form and made it multiple steps and that had this huge improvement in some outcome or you’ll see people point to really like seemingly kind like nuanced minutia stuff of like, “Oh, we changed this copy here.”

We repositioned this button and we saw a big shift. How do teams think about which of those areas to be focused on you just keep an eye out for both and as you’re continually researching chase down wins as you find them or should you start on one side and then go to the other, does that make sense, the big picture versus the details? How do you think about that?

Pulkit: I think firstly, those are headlines. It’s always sensationalists that get the headline. Most teams that are driving success are just chipping away at the problem, rigorous experimentation, continual changes, continual improvements. I think it depends how much you’ve already done. If you’re at the point where we haven’t touched our onboarding for like two years and yes.

It might be worth a little overhaul reset back to your baseline of what’s good now and what the patterns that people are used to now. One example is, I don’t know if you’ve seen this as well and now when I sign up for products, I don’t have to fill in a password at the beginning. I don’t have to create a password. I just put an email in and then I get a prompt later to create my password.

Now when I get to a product and it’s like, oh, set your past. I’m like, oh, this is weird. It’s old and it’s like, so that’s a pattern that’s changed. My context has changed so I think it’s important if you haven’t touched it for a while or you feel like maybe we’re outdated, then yes. Worth a big revamp and look for the big macro changes that people are doing or the new patterns that are being established.

Then if you’re like, hey, we’ve actually, our onboarding’s pretty good. We have a team that’s continually working on it. Then I think you’re looking for micro wins and say what can I do? That’s small tweaks and maybe I don’t know. That’s the best guess I have, maybe it is worth doing a overhaul or step back broadly. I think it’s similar to the general question. How do you not get stuck at a local Maxima where you’re continuing to iterate but you’re still in this but next to you, there’s a much bigger Optima or whatever deeper well or bigger peak. You’re not able to get out of it because you’re kind continuing to do this, the small changes. I don’t know if you have any thoughts to be interested but that’s where I think about it so far.

JH: No that makes sense.

Erin: Just like parting thoughts in terms of onboarding and research what should people know? As you said, I think big companies are different. They probably have onboarding teams that are exist in perpetuity and are constantly bright testing on onboarding but many companies are as included or not focused on onboarding 24/7, 365. In addition to not just working on onboarding, making it a project and then setting it and forgetting it, some other top tips or takeaways in terms of making the most of your onboarding.

Pulkit: I think ideally you have somebody who’s accountable for onboarding. That would be a good start even if they’re not working on it the whole time but it can be like if we need to make onboarding improvements, who do we go to or which team do we go to because that’s the team that knows about this or thinks about it. That would be a good start. Ideally, that team thinks about growth and engagement or conversion across product funnels generally.

Onboarding can be one of those funnels but maybe there’s a revenue funnel or sometimes there’s a monetization team or maybe there’s another funnel. Ideally accountability will help and second tip is to find a way to continually survey or research your users. Now you can do that through a micros survey that you set live and maybe you get those responses in a feed that, is visible to you.

For example, we send responses to Slack and teams like them collect their Slack. Then you’ve got people passively hearing and learning about what users are thinking and why they’re doing certain things. Finding a way just to continue to introduce that insight in a low effortful way would be good because then you’ll continue to build your intuition. I think instead of it being a every year, maybe if you’re not able to do it regularly but maybe every quarter that we’re going to review our onboarding metrics or activation metrics or actually we’re going to put them on a dashboard and continue to monitor them.

Bringing visibility to the things that you care about so that people it’s the same principle, passively making people aware of this will help drive more insight for when you do want to change it. I think maybe those are three good ones, having someone accountable trying to continually research and collect insights and then bringing those insights, whether it’s dashboarding or the feedback to people’s eyes regularly.

Maybe number four is just try to find a regular slot to also maybe do a review of your onboarding would be maybe good tips for improving onboarding more effectively.

Erin: Lots of good useful stuff in here. Thanks so much for joining us.

Pulkit: Pleasure. Good to chat about this stuff.

Erin: Thanks for listening to Awkward Silences brought to you by User Interviews.

JH: Theme music by Fragile Gang.

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