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As Director of Product Design at HBO Max, Michael McWatters knows a thing or two about welcoming people to a service. This week, Michael joins Paul and Rich to share why onboarding should be happening along every step of a user’s journey, not only as part of marketing. He draws parallels between online onboarding and in-store experiences and explains why you shouldn’t be training during onboarding — show, don’t tell.


Michael McWatters You know, I’ve been building flash intros for 25 years [Paul laughs], like onboarding is — [both laughing]. I know the value of an onboarding! 

Paul Ford Yeah, you have the right audience.

[Intro music plays for 16 seconds, ramps down]

PF Hey! Rich! How you doing?

Rich Ziade I’m doing well. How are you, Paul? 

PF I’m doing fine. So look, things are opening up a little bit, a friend came over the other day, came, sat on my porch, had a couple drinks, my friend Mike. 

RZ Sitting with your friend on a porch?!?

PF Good stuff. 

RZ Timeless! 

PF Classic stuff. And you know we talked [music fades out completely] about a truly, truly timeless subject. 

RZ Ok, so wait, it’s a nice night. 

PF Nice night. 

RZ In the neighborhood, friend of yours. 

PF He likes gin. You know, just chattin’ — chattin’ about life and then one of the great subjects of all time came up and I really, I feel it’s something that’s important. 

RZ French literature! 

PF Onboarding. 

RZ Ok. 

PF People listening to this won’t understand why onboarding is so important, we’re gonna talk about that. 

RZ Ok. 


PF It’s something we’ve never really fully addressed on the podcast before and it’s beyond time. 

RZ It is beyond time. 

PF And this is someone who’s thought a lot about onboarding, cares deeply about onboarding, and is also pretty— pretty senior in our industry. Mike McWatters, welcome to the Postlight Podcast. 

RZ Welcome, Mike!

MM Thanks for having me. 

PF It’s— we’ve got three good voices here. [Deep tone] Big! [Mike chuckling] Let’s go, let’s get into it. 

RZ Excellent voices. Excellent. 

PF Mike, you’ve been in the web industry two or three years now and [Paul and Mike chuckle]. Tell us your job. 

MM I’m Director of Product Design, HBO Max. 

PF At HBO Max. Now, people probably out there have opinions about HBO Max. I know Rich does. The other day— actually what was beautiful is Rich was complaining about HBO Max to me and you were complaining about one of our clients on Twitter. We don’t even need to play that out. But that’s not why we’re here today [Mike chuckles]. 

RZ I would say, though, I mean, even if the app required a crank— 

PF Yeah, you’d still watch. 

RZ Cuz HBO is just so good. 

PF Are you a Station Eleven guy?

RZ Station Eleven was amazing. Succession was just like eating bowls of ice cream [yeah, yeah] every time it was on. It was just so indulgent and awful and beautiful. They just consistently nail it. I feel bad for Showtime, a lot. I feel bad for Show— I feel like if HBO passes, they can get the Showtime meeting. And see if they can pull it off over there [laughs].

PF That’s actually what happened— that happened with Mad Men after The Sopranos. Like HBO passed on Mad Men and it went to whatever— [talking over each other].

RZ AMC, yeah. Defined AMC, right. 


PF We’re not going to interrogate you about HBO Max. 

MM Thank you. 

PF Ah— [all laugh] because I don’t want— I don’t want HBO’s PR and legal department involved in my life in any way. But, no, really when we were talking about onboarding, I’m like, “This is someone who cares about this more than I do,” and you know who else cares about onboarding more than I do? Richard Ziade. And I’m like, “Let’s all get in a room, and I’ll ask you guys questions about onboarding.” First of all, onboarding is one of those subjects, it comes up last, it should be first. Can someone define it? 

RZ When a user visits your experience, the default state is abondement. They’re gonna leave. The default state— and if you wanna be dramatic about it: failure. And you have a very small window to get them to engage and commit. Right? And that initial experience in some contexts it’s 30 seconds, in some contexts it’s a minute or two, is critical, and the experience you present to that user to welcome them onto the experience and to see value quickly, somehow, is how I would define onboarding. 

PF Let’s be clear, too, and I wanna actually get you to add some color to that, Mike, but we’re talking here about application style experiences as opposed to, “I’m gonna visit a website and read a news article.” Like, those deserve onboarding strategy as well but in general when you think about the web, I’m gonna hit a page and it’s gonna show me what it shows me, and then I’ll have that experience and we’ll see where it goes from there. 

RZ Yes. 

PF This is more like— Slack is a very good example, Slack has a rich onboarding experience. The first time you log into Slack, it’s like, “Hi! I’m Slack! [Mike laughs] How are you?” 

RZ Yeah, I think onboarding becomes more important— and then I wanna turn it over to Mike to give his version of the definition— if money is involved down the road, [mm hmm] onboarding is important. Now that may be through advertising, that may be through fees of some sort or subscription fees, it may even be through, you know, if it’s a game, in-app purchases where they’re gonna leave you alone about money for a little while to get you to feel real good and to loosen your muscles up so that you’re relaxed about the whole thing but— 

PF Sounds very bad. 

RZ It sounds very bad! But I think if money’s in the mix, you’re gonna have to think a little bit about how you keep people around. 

PF What is onboarding, Mike McWatters? 


MM So I’m gonna give one of those answers that people hate— 

RZ Oh no. 

MM — because— 

PF It’s great! 

MM I think your whole product experience is onboarding. So— 

PF Oouf. [Talking over each other]

MM Yeah, I know and it sounds annoying— 

RZ Oh, that’s an awful— Well, thanks, everyone, for listening to the podcast! 

MM Let me explain. [Rich laughs, Mike joins]

PF No, no, that’s— This is some, like, David Segall, Norman Woods kinda [Mike laughs], [in deep, nasal voice], “Nah! Ok—” Ok, go ahead.  

MM So, but no, you— I’m gonna get to what you said in a second, Rich, but like, you mentioned Slack. Today, I just noticed a new feature in Slack, so they had to onboard me into that feature. 

PF Is it huddles? 

MM No, I’ve been using huddles for a while, much to my team’s chagrin. [Talking over each other]

RZ I’ve been ignoring huddles for a while. 

PF So— I’m so tired— Slack— Slack and— is huddles good? 

MM Anyone who’ll huddle with me, I’ll huddle with. 

PF I understand. 

MM You wanna huddle? 

PF Well, frankly, I need someone to huddle with. 

MM Any kind of human contact [laughs]. 

PF No one I work with will huddle. 


RZ Get it back on track guys! 

PF Ok, so everything’s onboarding. 

MM Well, no, ok, so anytime you have somebody who’s engaging with your product, there’s an opportunity that they leave, and so what you’re always trying to do is build a relationship to get them to stay, obviously. 

RZ Yeah. 

MM That first moment when they experience your product, obviously that’s what we traditionally think of as onboarding.

RZ Yeah. 

MM But . . . I don’t think of it as a separate experience as defined by marketing. I think it is probably the domain of product, most of the time. 

RZ Yup. 

MM And I think that— The reason I think that is because good onboarding is the first leg of the product experience.

RZ Yup. 

MM It’s giving you the promise of what to expect [mm hmm], it’s kind of opening up to you and giving you a glimpse and making a promise to you as to what’s gonna be [mm hmm] but it’s doing so in a way that doesn’t feel threatening or obtrusive or annoying. And reducing friction.

PF Ok, I’m a product called Updog, who cares what I do, and you hit,, and you login and updog— a little dog pops up [right] and it says, “Hi! Welcome to Updog. Here’s the five things you need to do in order to be really successful at using Updog. Here’s your containers; here’s your pointers; and here’s your shoe finder!” Right? And it’s just like, “Here they are, bah bah bah,” “Ok, dismiss!” I did my onboarding, am I ready to subscribe? So that’s onboarding for Updog. 

MM Right. 


PF Ok? Now you’re telling me, “Hold on a minute, you gotta think a little deeper than that.” What would that be like? What does that feel like? 

MM I mean, first of all, I’d say that’s a horrible experience.

PF Ok, fair enough. 

RZ Yeah, I’m not gonna use Updog. I’m just gonna throw that out there. 

PF What’s Updog? 

RZ I’m not using it. 

PF Ok. 

RZ I just— 

MM It’s where you get your updog or, I mean, downdog. No more dad jokes. It violates—- it’s like, first of all, it violates kind of the rule of like, I don’t think you should ever be educating during onboarding. Like, not explicitly educating. It shouldn’t feel like training. 

PF Oh, interesting, ok. 

MM Like show, don’t tell. If it feels like you’re trying— I mean, whenever I hear somebody say, “Well, we need to train users.” It’s one of those words— First of all, I hate the word user, second of all, don’t train them. 

PF What do you call humans who do things?

MM Whenever possible, in technical documentation, I call them people. 

PF Ok, that’s nice. That’s good. 

MM So people are watching our product, not ‘users are consuming our content’. 

PF Ok. Ok. 

MM And I do that because I actually think if you are talking this way about them in general you start to humanize them in your mind. Anyway, a little backstory: when I was starting out, way as a kid, I thought maybe I’d be an architect. [Ok] What interested me about architecture was the way that you introduce people into buildings, into spaces, obviously Disney and so forth. I always think about real world parallels. If you were to walk into Updog’s brick and mortar [mm hmm] and somebody came out and started handing you pamphlets of things you needed to know, you would leave that store right away. 


PF Be awkward, it is— 

MM Yeah, exactly! It’s like when you walk into the store and you need the salesperson but you also kind of don’t kinda wanna ask for the salesperson, you know? 

PF Yeah. 

MM You want them to be there when you need them— 

PF You know there’s a store, I think it’s Microcenter. No, it’s not Microcenter but it’s like some relatively nerdy store. And there’s like a little flag you can put on your basket that’s like, “You can talk to me.” When you’re going to buy your Raspberry Pi Zero [Mike laughs] — 

RZ You don’t wanna be upsold USB, a lot of cables, yeah— 

PF No, that’s between you— that’s between you and the home slash hobbyist section. 

MM You and your creator. 

RZ It’s actually between you and your god. 

PF Exactly! [Mike laughs] And so like, that’s an interesting way to approach it, so think about what it’s like when somebody walks into a space and— 

MM A hundred percent. 

PF — how you make them feel comfortable. What are some good onboarding experiences between the two of you? 

RZ Keying off of what Mike’s saying here, games on phones I think are the gold standard, in my view. 

PF Yeah? What’s a good phone game? 

RZ There’s a great game, it’s in Apple Arcade which is a subscription service [yup] that gets you a bunch of games, called Agent Intercept. 

PF Ok, I’ve never heard of it. 


RZ You’re a spy but you’re really driving cars and boats. 

PF Ok. So it’s a driving game or whatever. 

RZ Near zero skill required, it’s just very satisfying to play. But when you first start the game it opens like a spy movie, with music and— 

PF Ok. [Sings in the style of Mission Impossible-type theme song] Dun tuh dun dun tan dun dun! 

RZ Yeah. 

PF Ok. 

RZ And then the car gets dropped off of a plane, a cargo plane opens up, your car flies out and parachutes out. The minute it hits the ground, it pauses with, like, an action font, showing up saying, “Agent Intercept”, and then the next thing it does is it teaches you how to like move and shoot missiles in the game. 

MM Right. 

RZ Meaning, you’re learning by doing, rather than, like—

PF Like you move a little bit— 

RZ — flipping through a— yeah, you move— 

PF And it stops and it says like, “Shoot the missile at the other spy!”

RZ That’s right. But here’s the thing that they do: they put a dump truck in front of you [yeah] and not only are you gonna shoot that missile, but you’re gonna win. Your first moment is actually a little dopamine hit. 

PF You get to blow up the dump truck. 

RZ You’re gonna blow up that truck and there’s such an immediate— you didn’t just learn, you actually found like a hint of what the joy can be in the game. Right? And I find that games on phones put enormous energy— first off, the potential user base is so wide [mm hmm], like my mom plays games on— she’s 70-years-old— on phones. 

PF Sure. 


RZ They’ve put the bar so high as to— in terms of the— 

PF It has to be accessible to everybody

RZ Everybody, everybody. And I love that the learning happens in the experience rather than over on the side in school. 

PF Right. 

RZ That to me is the gold standard, in my mind, it’s hard to wedge it into other scenarios where there’s more complexity and you gotta get a credit card out and all that but to me that’s inspiring, consumer engagement and the work that goes into it is somewhat inspiring.

PF When I say ‘good onboarding’, Mike, what pops up in your brain? 

MM So, ok, when I came in today, you guys did your due diligence, you gave me a COVID test. 

PF Yeah. That’s right. Postlight currently has a limited number of people who come in the office and everybody takes their rapid test when they come.

MM Right. Now that we’re in Omicron, though, buying rapid tests like a maniac a couple of weeks ago cuz [sure] my kids needed them to go back to school, and I’m going from one pharmacy to the other and buying different brands because no pharmacy will— I’m hoarding rapid tests. 

RZ Yeah. 

MM And the first one I take out, it looks like what you’d expect. It’s like a pharmaceutical box, that weird paper, you open it up, a bunch of things fall out and then basically a map-size piece of paper with two-point type. 

PF Yeah, horse blanket sized posters. 

MM Yeah, now I realize I should have gone to medical school and I’m a phlebotomist and I have no idea what the hell I’m doing. Right? 

PF Yeah, yeah. 

MM And I’m intimated, you know? And if I screw up, I just spent 20 or 30 bucks on this and will my kid get to go to school or am I gonna go insane for another week? 

PF Yup. 


MM And then one of the next ones— I tested my other son— can I use a product name? 

PF Yeah. Yeah, go for it. 

MM I think it’s called Ongo. It comes in this very stylishly designed modern pack— same size box, everything. It says right on the package: take your phone and scan this QR code. 

PF Ok. 

MM Lovely app. Literally demystifying, works perfectly, downloads, just walks me through the whole test, step by step, “Push this button, the timer will start for 60 seconds”. “Beep, now it moves it to this thing.” It’s like showing me in lovely illustrations how to do it— 

RZ A lot of visuals, in steps. 

PF The test itself is not integrated with the app, it’s just guiding you through it. 

MM Well, at the very end actually— So at the very end you are supposed to photograph your stick and it actually— it basically confirms what you were saying, [ok, yeah] and then you can use that to send it as an official document which the others don’t have. 

PF Oh, ok. Yes, but you could also just look at it. 

RZ Yes.

PF But if you need to prove to the people or at a school that you did this, you could do it with that. 

MM Right. 

PF Yeah, ok. 

MM And so the point, for me, was like— my first experience with a COVID test 15 minutes earlier with my one son was like a horrifying medical experiment with tiny type and where do I start and what do I do? And I’ve got all these bits and pieces. The other one had all the same parts, the same test, the test wasn’t different, but the experience of opening the box, getting into— it has an app, in the first place, but then very gently walk me through with comforting animations and really nicely written product copy. I’m suddenly feeling very confident about the results— of course, he tested positive— 

PF Ugh.

MM — which was not— 

PF But you were confident about the results. A wonderful place to think about this is the gym. Gyms can be the most intimidating and terrible place in the world. 

RZ Yup. 


PF And they can be very inviting. Sometimes there are gyms that are, like, too inviting. Like everyone jokes about Planet Fitness just having pizza which is probably not productive. 

RZ That’s not a gym.

PF But if we go back to— like, your experience, Richard, the one that you’re talking about, it would be like, “Hey, welcome, you know what? You guys are in the— you’re in Group A, let’s go and we’re gonna try all the equipment, right now. It’s gonna be fun. We’re gonna get a good burn goin’ in the next 15 minutes and then it’s gonna be up to you, you can figure out how you wanna use this gym.” For you, it’s much more like Experience A is like, “Ok, come on in, we’re gonna look at you and we’re gonna tell you exactly how each piece of equipment works and if you screw it up you’re in big trouble.” Versus, like, “Hey! Watch this cool video that tells you how to do everything that you could wanna do here at the gym.” That’s where people are at. They walk in— Like, the COVID test is a good mental model. The game is funny because I think people are— you’re actually slowing people down with the game. [Yup] You’re saying, “Hey, ok, I know you wanna do this right now. I know you have no impulse control and you just wanna smash the screen. [Yup] But, God, if you just let me tell you [Mike chuckles] three things, you’ll have more fun and we’ll all feel better about ourselves.”

RZ Yes. But what’s interesting about what you’re saying is there was no option to get out— 

PF Yeah, oh no, and they’re gonna— 

RZ Like, first off, they were like, “This is gonna be 30 seconds and we’re actually gonna make it fun.” 

PF Yes. 

RZ “We’re actually gonna make you enjoy yourself for the first minute and then you’re off to the races.” 

PF People will do it! People will do it. 


MM You’re already invested. You’re already emotionally connected. And that’s what you’re hoping to do is get people through that— 

RZ That’s right. 

MM — where they feel like they have— either some sense of emotional investment or some sense of ownership. 

RZ Yup, yup. 

MM By ownership I mean the minute they enter some data into your app, the minute that they are starting to actually build a portfolio or, you know, create a profile or something. They’re starting to build a relationship. 

RZ Yes. I think we’re all really on the same frequency here in terms of what works. I wanna talk about a more painful scenario which is— I don’t know what the word to use, I wanna coin a phrase right here on this podcast. 

PF Go ahead.

RZ Call it slippage. 

PF K, slippage. 

RZ It looked promising for a minute, if like all the little analytics beacons were like, “Ok, it’s firing off, we’re taking them through the journey.” And it went dark. They came in, they logged in a couple times last week and then haven’t logged in ten days. Right? And I think we often look at tools as like, you’ve got one shot. They’re comin’ in. There’s your chance. 

PF Never gonna see ‘em again.

RZ Never see ‘em again. We’re incubating product right now outside of Postlight and I’ve been trying a lot of tools that are in the space and there is nothing more grating slash fascinating to me than these desperate emails that I get from these products—

PF Ohhh God. 

RZ— that I tried for like four days— 

PF Yeah. 

RZ — and then bailed on. One said, “Rich, we miss you!” 


PF So but they got— [Mike and Rich laughs] The minute— the minute you let a software product get your first name— [Rich laughing]. You’re in hell.

MM You’re done. Right, like your email. 

PF Yeah, cuz that’s all they need. “Hey Mike!” 

MM Yeah. 

PF “Looks like you tried it but didn’t like it, wondering [Mike laughs] where we coulda done better, buddy?” 

RZ How can you recover from what appears to be abandonment. Is there a way? And that is, to me, how do I get you back in? And the only thing that’s worked for me, I’m a savvy user, maybe these techniques work. If no one said, “Hey Jim,  we miss you,” in his life, for many months, it’s really nice to get that email from 

PF The great— nah! The great misalign there— 

RZ Isn’t it?!?

PF So many people sign up for my email— I have, like, an old Gmail address. 

MM Yeah. 

PF And people sign up for, like, all their intimate things using my Gmail address because they just don’t understand. And it’s like a cannabis supply shop in New Zealand [someone snorts]. So I’m in these chains. Over and over. 

MM Ok. 

PF And I can’t reply, there’s nothing I can do. I just watch, they come in and I can’t get rid of them. And what you see is just like— the thing that you were talking about earlier, Mike, where it’s just like, they forget that they’re in the store, right? They’re just sort of, like— they forget that there could be a relationship here. 

MM Yeah. 

PF And the problem with our medium, in general, is that it’s so cheap [yeah] to send somebody a message. It’s so cheap and it’s also very expensive to get someone to actually, fully onboard onto a product, give you a credit card, et cetera. So, the cost for an email is fractions of a penny. The cost for acquisition of a user could be— 


RZ They know they’re annoying. They’re not stupid. They’re just like, “You know what? We’re gonna hit two percent of these and we’re gonna keep going.” 

PF It might cost you 250 dollars every time you onboard a user for your CRM.

RZ Yeah. 

PF Right? Because that’s a 30 buck-a-month per seat license, so they’re like— in their head they’re like, “Well I get about 2,000 emails on this person alone. Right? I can just go to town.” And so you just end up in this merciless situation because their analytics tell them that, “Well, yeah, 99 percent of people just absolutely hate but that one percent is pretty good and that’s what’s gonna pay for me. So, why not?” 

RZ One of the things the world has accepted is that three percent, four percent is spectacular success. 

PF How the hell do we get past this though because it just sucks to live in a world where you send someone 90 emails to beg them to use your product when, in reality, you should find out why the product isn’t good. 

MM That, to me, is the issue. Like, if you’re having to do that there’s something wrong with your onboarding. And now I’m talking more straightforwardly about what you were talking about, onboarding is the initial contact. I’m not opposed to the follow-up email. Although, I kinda like follow-up emails that are funny and honest which are like, “Hey, you know what? There’s three reasons why you didn’t come back,” and maybe you list two legitimate ones and one kinda joke one [yeah]. At least you’re saying like, “Hey, we found that people leave because whatever.” 

RZ Ok, so this is good advice: come back with a wink and just acknowledge that you’re buggin’ the person. 

MM Yeah, right. I mean— I mean, using a real world analogy, when did hounding somebody who turned you down at a bar ever work? Like, it doesn’t work. 

PF Yeah. 

MM You know, your best option is to pivot or walk away. 

PF Yeah, if people acted in real life like they do [that’s right] in emails, they’d all have to go to HR and have a real serious talk [Rick laughs boisterously]. 


MM You know— can I— can I tell you? Like, I always say, I am the user, I’m not the user. In fact, I’ve written about this but I’m like— or you are the user. We have to check ourselves, we are willing to do things to our users, to our customers, that we would never want done to ourselves and we justify it because it works. 

RZ It’s harassment! 

MM Right? It is harassment. 

RZ It’s harassment. 

MM But to the other point is you’re right, emails are cheap. But you can’t look at them that way. Why are so many people abandoning at this point? Now if you see patterns in your analytics, that’s when you have to do more than just look at analytics, you have to do user research. So, an example would be: I’m at Updog and I’m learning that 50 percent of the people are bailing at this one screen, right? Now I gotta go—

RZ At some step in the journey. 

MM Some step, right! I gotta go to user research and figure out why and I bet you the mistake you’ve made is you were selling when you shouldn’t have been. And what I mean by that is you’re still promoting or— or you’re not giving enough information, you’re not previewing. And the truth is the person is probably dealing with some other issue if they’re at that step which is like, “Am I gonna be able to get out of this trial?” “What are they gonna do with my credit card?” So at that point during the onboarding, maybe it’s less about enticing them in— 

RZ Yeah. 

MM . . . and addressing whatever concern is suddenly on their mind at that point. 

PF You skipped forward a little bit, though. Go do the user research, how do you do that? What does that look like?

MM I mean it really depends on what you have in terms of your resources. 

PF So, it’s Updog, I have an analytics report, I know the users, and I’ve convinced a few people, I’m gonna give ‘em 200 dollars to talk to me. Ok, so now what? 

MM You can ask people who have dropped out, why they dropped out. “Can you tell me—” Of course, it’s hard for them oftentimes to describe it. But for this kinda scenario I would probably recommend actually moderated user testing with people who haven’t dropped out, like people who are unfamiliar with your product, and you wanna see what their experience is like, and you’re asking them questions along the way, and you’re trying to figure out, like, “What’s on your mind on this screen?” You know, “When you get to this screen what are you thinkin’ about?” 


PF So almost like focus group level stuff. 

RZ It’s very observational— 

MM Exactly. You’re trying to understand— look at the way I like to do moder— And I’m not a user researcher— I do user research, I’m not a user researcher. I’m very fortunate where in that we [sic] have actual user researchers but a lot of it is really a conversation. And you’re watching them and you’re asking them to voice over what they’re thinking. Like, “Go a little slower. What’s on your mind on this screen?” They might say, “Like, you’re asking me to start a trial but I’m wondering, ‘Am I gonna be able to get out of this trial? What are you gonna do with my credit card?’”

PF ‘Go a little slower’ is a really good point. Ok. 

RZ I wanna be more explicit about what Mike is suggesting because I think there’s an absolute key distinction and this comes out of the design, like the user research design world, and I think, and if I’m not mistaken, Alan Cooper has emphasized it in a couple of his books, which is if you ask people in an interview setting, “What do you think we should do differently?” You don’t get the real gold. But if you ask people to describe what they’re doing, while they’re doing it— 

MM That’s right. 

PF Right. 

RZ — it’s very different. Because people either aren’t paying attention, feel they have to perform cuz you just asked them a question and they’re feeling important in that moment, but when you’re asking people to describe, “Why’d you just do that? Can you tell us what your thinking was when you were doing it?” while they’re doing it, you’re no longer putting them on a stage, but rather asking to be very descriptive of what they’re doing. 

MM Sure. 

RZ And I think that is hugely valuable and we’re a fast-moving org, Postlight, and we would love to do that kinda work. I don’t think enough people do it, frankly—

MM Right.