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61 / Simple Steps for High-Touch User Engagement

Hosted by Sean Flaherty & Matt Bush



Rob Fitzpatrick Headshot

Rob Fitzpatrick

Entrepreneur, Author

Rob Fitzpatrick is an entrepreneur of 13 years and has written three books about his learnings along the way, including the best-selling handbook for doing better Customer Development, The Mom Test: How to talk to customers and figure out if your business is a good idea when everyone is lying to you.

Back in 2007, he dropped out of grad school to go through Y Combinator with his first startup and has been building products and businesses ever since. Beyond software, he has also kick-started a physical card game, built an education agency, and more.

A programmer by training, Rob was forced to learn enterprise sales the hard way at his first company. With a foot in each of those worlds, and with his experience both bootstrapping and raising funding across a wide range of products, industries, and business models, he offers a broad and balanced view of the entrepreneurial journey.


Maybe more than anything else, product people want good, honest, relevant feedback about their products. And their go-to source for the straight-up truth? Moms and best friends. They’re the ones who’ll give you the sort of “big-picture feedback you’re desperate for.” And the best part is they know enough not to give advice you didn’t ask for. This is the “mom test.”

In this episode of the Product Momentum Podcast, author-entrepreneur Rob Fitzpatrick joins Sean and ITX product strategist Matt Bush to discuss how best to do product discovery and get answers to these questions: “How do I get people to talk to me? How do I know if I have enough feedback? How do I figure out if I’m building the right thing?”

In his book, The Mom Test, Rob writes, “It’s not everyone else’s responsibility to tell you the truth; it’s your responsibility to go out and find it.” Coupled with his personal rule – i.e., to build products only for customers I actually want to be friends with – and you’ve got a recipe for product success. Even more than that, though, you’ve got a blueprint for research, discovery, and engagement that leads to better products and more interesting stuff to work on.

Listen in to catch more of Rob’s “how to’s” on user engagement and workshopping:

  • How (and where) to initiate the perfect learning conversation
  • How keen focus on your MVA will help you build your MVP
  • How to recognize compliments as the red flags that you’ve started asking bad questions
  • How to match the 5 teaching formats with the type of content you’re teaching

Sean [00:00:19] Hello and welcome to the Product Momentum Podcast. This is a podcast intended to entertain, educate, celebrate, and give a little back to the product leadership community.

Sean [00:00:32] Hey, Matt, how are you doing today?

Matt [00:00:34] I am doing fantastic, Sean. That was a great conversation.

Sean [00:00:38] That was a great conversation with Rob Fitzpatrick. He’s written two books that I think should be on every product leader’s bookshelf, The Mom Test and The Workshop Survival Guide. I’m really blown away by the conversation.

Matt [00:00:50] Yeah, me too. There were a lot of fantastic insights, a couple of different quotes that could come up. One of the ones that stood out to I think both of us was the concept of allowing yourself to be suboptimal, be able to be good enough, but you don’t need to be perfect. I think that just resonated really well, at least with me.

Sean [00:01:08] Yeah. My favorite quote was that “some problems don’t actually matter, even if they technically exist,” and you have to figure that out quickly. Anyway, let’s get after it. I’m excited to share this content with the audience.

Matt [00:01:19] Absolutely. Let’s do it.

Sean [00:01:20] All right.

Sean [00:01:23] Well, hello and welcome to the pod. Today we have Rob Fitzpatrick. He’s an entrepreneur of 13 years and has written three books about his learnings along the way, two of my favorite books in product, The Mom Test and How to design and teach (educational) workshops that work every time, The Workshop Survival Guide, which if you’re a workshopper or you’re on design sprints, anything like that, I highly recommend you read those books. But I’m excited to talk to Rob about his learnings in the product leadership space. So, Rob, welcome to the show.

Rob [00:01:49] Thank you so much for having me, Sean. It’s a pleasure to be here.

Sean [00:01:52] What’s got you inspired lately? What have you been thinking about?

Rob [00:01:55] After a couple-year break, I jumped back into the arena and I’ve been building kind of a community-first software business and it’s got all the pieces. So it’s got the community, which is amazing because you can monetize it upfront and it’s like turbo-charged customer discovery because you can see where people get frustrated, where they get lost. There’s a book, which is up for presale, which kind of leads people in the education side, and then there’s software on the back. It’s so much fun. It’s such a high-touch, high-contact way to engage with customers. We’ve got about 100 people in there right now. And it’s just been a blast. It’s for people writing nonfiction books.

Sean [00:02:29] Neat. It’s like a book as a product.

Rob [00:02:30] It’s all of it. I mean, the book is the cornerstone, right. People read the book and then they go, “ah,” and that leads to the community. And then the community is paid, they pay monthly, and that acts as a holding pattern until they’re at the point in their journey where they’re ready for the software. And so I feel like it’s so much fun seeing how these three pieces fit together. And, you know, we’re still in the early stages. It’s about two thousand per month in revenue right now, but I’m happy with it. All the questions and the risks and the fears I had around other types of businesses, like, “ah, how do I get people to talk to me? Oh, how do I get enough feedback? Oh, how do I figure out if I’m building the right thing?” I feel like this structure just trivializes all of that.

Sean [00:03:04] Yeah, that’s neat. That’s a neat project. So I want to ask you a couple of questions about The Mom Test. So jumping right in, here’s a quote; “it’s not everyone else’s responsibility to tell you the truth; it’s your responsibility to find it.” And I guess the key learning from that book is you do that by asking good questions and not accepting compliments.

Rob [00:03:24] Exactly.

Sean [00:03:25] I’d like to hear about that. In your journey of this new endeavor.

Rob [00:03:28] Product people always expect everyone else to tell them the truth, right. They shift the burden of truth to the customer or to the user. They go, hey, do you want this? Hey, do you think you would use this? And that’s hard, because one, people are really bad at predicting their future behavior. I’m sure any of you listening who have done some user research or asked for customer feedback, you know this to be true. And also it introduces this ego element where you obviously care about your product, right, regardless of whether you’re an entrepreneur, it’s just the thing you’re building. You care, otherwise, you wouldn’t be doing it. And so it’s hard for other people to say, “actually, this doesn’t matter to my life whatsoever; I wouldn’t lose a wink of sleep if this didn’t exist.”

Rob [00:04:04] And that’s the kind of existential, big-picture feedback when you’re deciding if a product is worth building or if you’re targeting the correct customer segment or if you’re describing the positioning and the proposition in the correct way, that’s the sort of existential big-picture feedback you’re desperate for. And people just don’t do that. And so instead we go, “Hey, here’s the idea, what do you think?” And in addition to introducing biases, that also zooms the conversation in on feature suggestions: “Oh, is it going to integrate with Excel?” Meanwhile, they wouldn’t even use it in the first place. So all of that feedback is completely irrelevant at best, and at worst, actively misleading. And so, yeah, it’s about how you structure the conversations to avoid the biases. How do you ask the questions? It’s stuff that, you know, user researchers and ethnographic researchers have been doing for years. But often in the product world, we have to do this stuff alongside our job. We don’t have all the classical training. So the mom test is kind of a quick and dirty way to get to the good enough results and avoid those misleading biases.

Sean [00:04:58] Yep, for sure. So you touched on something. You said, “you care about your product, obviously, that’s why you’re there and you’re spending your life energy building this thing.” And if you’re not, you might be in the wrong role. Like, that’s a question to ask yourself, right.

Rob [00:05:09] So my first business, this was thirteen years ago. We went through Y Combinator. We wanted to build a scalable startup. We raised funding from really good investors. We had a couple of great early customers, Sony, MTV, a few other big household names, and then we realized that we hated the industry. We didn’t really care about the product. We’d essentially pushed ourselves that far, not because we cared about what we were doing, but because we cared about the idea of being successful by doing something and it seemed like a good spreadsheet product. Like on a spreadsheet, the number in the bottom right looked very appealing, big, growing market, et cetera. But that’s not much reassurance four years later when you’re in the depths of the grind, you know, and you’re trying to stay motivated. And after that, I kind of made this personal rule that I’m only going to build products for customers who I enjoy hanging out with…

Sean [00:05:51] Oh, that’s a good rule.

Rob [00:05:53] …and who I actually want to be friends with. And it’s such a business hack because people go, “how do you get customers to agree to interviews?” It’s like, well, you like them and you care about their lives. People love talking about their problems with someone who cares and is trying to fix those problems. They don’t like talking about their problems with someone who’s trying to figure out how to monetize them in a cynical fashion. Also, “how do you get the first person to talk?” Well, I know them, they’re my friends, like everything that’s so much easier with that rule.

Matt [00:06:17] Yeah. Listening into The Mom Test and actually going through the book and everything, I thought it was fantastic. I thought there were a number of different great learnings to pull from it. One of the ones that I kind of keyed in on and you touched on it already a little bit, was the kind of keeping it casual. You don’t want to keep things really, really formalized or anything like that. And I’m curious to poke on that a little bit because of kind of the day and age that we’re in. You know, everything is remote and everything needs meetings for different things and everything. But how do you see being able to keep things really casual still while still having dedicated meetings but not being able to meet in person, like not having that cafe to be able to go through and to talk to, especially working with communities, the way that you’re starting to.

Rob [00:06:56] It was much easier in person. I relied heavily on what I called the serendipitous customer learning where I would go to where my customers were likely to be hanging out, and then I would find an excuse to get chatting with them. And so if I was trying to understand email security, for example, at law firms, like let’s say they were one of my customer segments, I would go find a cafe or a bar across from a law firm, you know, and I would hang out there and I would kind of wait for people I’d to strike up a conversation; “hey, super crazy question…” Or I’d go to a meetup and do it like that. Obviously, that’s no longer possible.

Rob [00:07:25] And it used to be that the culture on video calls was that people wanted to get work done and get off the call as quickly as possible. And now after COVID, that whole culture has changed. And it used to be impossible to get to know someone through a call. And if you said, “Hey, I’m going to show you the product, but first, could I just ask a couple of questions about how you’re already dealing with this?” They would get angry at you because they felt like you were wasting their time. They always saw the video call as a get-work-done second-class citizen, and now they’re actually happy to open that space, to have a bigger conversation. And so I found that the quality of remote customer learning has gone way, way up since COVID just because the culture around it has changed.

Rob [00:08:00] Also, there’s things like a lot more activity in online communities. So, for example, the one I’ve been running, it’s for nonfiction authors, and the product, the software I’m building is helping them to build a better book, get better feedback, etc. On the journey toward that, there’s a million traps and places they can fall over, et cetera, and so the value proposition of the community is the same as the value proposition of the product. But it’s more general. It’s like, “Hey, we’re going to help you make a better nonfiction book.” And by promising that up-front when they join, that’s their expectation. And so they go, “Hey, I’m stuck on this; hey, I’m having trouble with this; hey, I was wondering about this.” And that’s a goldmine of customer learning. So the community is an ultimate hack. I’m not sure it applies to every industry. In fact, I’m sure it doesn’t. But for the ones it does, it’s so, so worth the time. Plus you can monetize it directly. It’s win, win, win.

Rob [00:08:48] Apart from that, I’ve been also using a little bit more of what Amy Hoy and Alex Hillmann call the sales safari, or the customer safari, where instead of explicitly asking people, you’re doing more like ethnographic research, where you’re going to these public online spaces where your customers already gather, talk, ask questions, and complain, and then you’re just watching what they’re already doing and talking about. That’s not going to answer everything. You’re not going to get validation about whether they want your product in particular. But for this initial layer of customer understanding, it can be quite powerful. And it’s nice because there’s very little bias.

Rob [00:09:20] But then to get back to your kind of original question about the formality and keeping it casual, I’m sure you’ve been in these formal… You go into a boardroom and it’s all glass and mirrors and it looks very fancy and someone goes, “so, tell us about your budgets.” And you’re thinking, “no way am I telling you anything about my budgets,” because just the context puts you in a defensive mode where you feel like anything you say is going to be used against you in negotiations. Whereas you meet that same person who asked that same question, but you’re in a cafe and they go, “Hey, what are your budgets like for this?” You go,” oh, it’s costing us a fortune, you know, we’ve got a team of five freelancers, it must be two hundred grand a year.” And they’re going, “oh, why are you doing it that way; why haven’t you..?” It’s like, boom. That’s a perfect learning conversation. Nothing changed about the questions, you just changed the context and so the shields go down.

Rob [00:10:02] And part of the trick online is that every meeting becomes a sales or a demo meeting by default, even if you’re still pre-product. And so you need to kind of control and frame that. And the way I do it, is I say, it’s vision, framing, pedestal, ask. Still ask, so I go, “Hey, I’m trying to improve the education industry, for example, but I’m having a lot of trouble understanding how universities think about software behind the scenes, how you decide what to buy, how you budget it. You know more about this than anyone. I’m having such a hard time figuring it out. If you were just willing to spend 10 minutes talking me through how you make those decisions, it would save me months. I’d really, really appreciate it.” And so then you’ve given them a clear reason for the conversation where they know that they, in particular, are going to be able to help you in particular, which is what people want. They want to help. They don’t want to have their time wasted. So you’ve clarified them not wasting your time, there’s a way you can help, and you’ve made it not a sales meeting or not a demo meeting. So that’s how you open up the space. And then they’re like, “yeah, what do you want to know?” You’re like, “how much do you pay for this? Why do you do it that way? What else did you try? Which products have been a huge disappointment?” You know, all of that stuff. And then you’re in a great learning conversation.

Sean [00:11:01] Yeah, I have to say, Rob. I went back and listened to your book again and the style in which you recorded it was so unique. You sound just like you do on the podcast like you’re having a conversation with me. And anyway, I really appreciated it.

Rob [00:11:12] I listened to a few business audiobooks before I gave up on the category, and I feel like every book has the exact same pacing and intonation and it’s like, come on, like, “talk to me like a human being,” right? It’s like they’re being read by an expensive robot narrator who, like every word, has equal weight and value. And it was like, “Nah, I’m just going to talk through this like I’m explaining it to a buddy.” So that’s what I did. I rented a by-the-hour kind of conference room in Barcelona, put a blanket over my head, and just recorded it off my laptop because I didn’t have the budget for a fancy setup and I thought it was more important that I do it as a human than that I really crank the production value.

Sean [00:11:48] Yeah, well that’s a plug for the book. The first time I read it, I read the hard copy. The second time it was Audible and I definitely enjoyed the Audible more, which is unusual for me. I actually like to sit down with the book and read it because then I can tell the story in my own head and do the visualizations in my own head, you know. And I definitely, again, plug the book. I think it should be on every product person’s bookshelf. If you do any user research, it’s super important. So along those lines, you talk a lot in the book about why you think we’re bad at talking to customers, and example after example that you gave, I was like, “yeah, that’s exactly right, and I’ve done it myself,” you know? So I want to hear about that.

Rob [00:12:23] Which stuck out as the, “oh, that’s the one I keep doing.” Was there a mistake that struck close to home?

Sean [00:12:28] The key thing is, like, we’re so in need of affirmation of the work we’re doing that we just, we’re blind to like the compliments, you know, and I think we take them and then the conversation becomes, “what do you like about that?” and, “do you want to hear more about that?” as opposed to, that’s not what we want, like listen for it and put it out. Like you want the negative feedback because the reason you’re doing this is to improve.

Rob [00:12:49] Yeah. Like, you can always get someone to say that your product is amazing. If you’re annoying enough about it, you know, you just don’t let them leave. You give them the page, they go, “huh, interesting, yeah I’m not sure it’s for me.” And then you go, “no, no, you don’t get it,” and then you re-up your pitch and then next thing you know, they’re going, “wow, yeah, it’s so visionary, you’re so amazing, what a great product; I’m sure everyone will use it.” It’s like, oh well, you had the truth, right? Which is that they didn’t care. The disinterest is the data. And then you threw it away because you were so desperate for the compliment.

Rob [00:13:17] And I will say that in larger companies, I’ve talked to a few big Fortune 500s about doing this because this sort of approach is not necessary if you’re doing incremental advancement. So now cell phones, everyone kind of knows what they want a smartphone to do so you don’t need to go do this deep qualitative research. But if you’re building a new product category or you’re entering a new industry, it’s very valuable if you’re doing something new. And so these big teams, they’re like, “OK, we know the traditional market research playbook for incremental innovations, but we got confused on disruptive innovations.” So I’ve got to spend some time.

Rob [00:13:47] And the thing that kills them is the management reporting chain because people feel like their job is under threat if they report to their manager, “Hey, I did the research and it turns out no one cares.” Actually, you need to be free to find that result. And that doesn’t mean the whole project is dead. Maybe it’s positioned wrong. Maybe you’re talking to the wrong customer segment. Maybe… There’s a million things you could fix, but that particular version is not going to work, right? So you go, “OK, what does this mean?” And sometimes if you’re scared of reporting that up or if management doesn’t want to hear it or if they want everything reduced to a pie chart, then you end up with this non-data, like, “95 percent of people said it’s a problem.” “OK, well, how much? Like, ninety-five percent of people say recycling is a problem and they still don’t do it, you know, or that power waste is a problem, but they still leave all their electronics on all day. What people say isn’t necessarily what they’re going to do. So you need to feel safe in reporting the negative.

Sean [00:14:37] There’s a Margaret Mead quote: “what people say, what people do, and what people say they do are three independent variables.”

Matt [00:14:43] Yeah, some of that stuff, as you were talking, Rob, really resonated, like the whole reporting structure and being OK with the negative feedback and stuff, because that was one of the things that I pulled out of The Mom Test as well, was the compliments. I fall into that trap a lot. Like, OK, you hear compliments and it feels great to hear compliments, but trying to get to that other feedback that you’re really, really looking to in order to improve. So I really like that statement of being able to report up.

Rob [00:15:09] One useful role that the compliments play as they act as a signpost that you’ve screwed up the conversation and that you’ve started asking bad questions. So if your customer is complimenting you, you’ve messed up further upstream and so it acts as a mental reminder to be like, “whoops, I wasn’t talking about them, I had started talking about my idea.” You can’t get a compliment if you’re just asking about them. The compliments come, by definition, when you’re pitching your idea and you go, “oh.” And obviously, you have to pitch at a certain point, but when you do, you’re not doing it for compliments, you’re doing it for money or commitments or advancement, even a referral to their decision-maker. And so the compliment is like, “whoops, I’m screwing it up.” And you can often rewind. You can say, “whoops, sorry, I got excited; you were telling me something interesting. You were saying —, would you please continue,” or like, “could you tell me more about that?” And then suddenly you’re back into good, unbiased questions.

Rob [00:15:52] And that’s also why it’s so important to take notes because you want to go through the transcript. If you don’t take notes, you’re like, “wow, they loved it.” But then when you read through the transcript, you go, “wow, I set them up; I backed them into a corner where all they could do was compliment me because they’re trying to get out of here.” And the transcript really helps to sort through the good data and the bad data.

Sean [00:16:09] Yeah. So let’s transition now. I want to talk about The Workshop Survival Guide. It’s become more and more important, I think, in the product leader’s toolkit to have workshopping skills. And again, another book, I think if you workshop, you should have this thing on your bookshelf because it’s got a lot of really interesting tactics in it. So let’s start. I want the audience to hear about the five essential teaching formats from the book and your thoughts on blending them to produce the best possible workshop experience.

Rob [00:16:37] So the idea of this is everyone wants to lecture or maybe they default to lecture, plus their one comfort format. So for business school teachers, it’s case study exercises. For other types of people, it’s whatever, like Post-it Note walls. Everyone’s got a comfort format, but actually, each kind of mode of teaching and this is lecture, small group discussion, case study challenges, try it now practice areas, Q&A, these different formats, they each have a different energy profile and they have different consequences for the attention level and the energy and the engagement and the goodwill of your audience. And also importantly, and something vastly underappreciated, is that they’re each good at teaching different things.

Rob [00:17:17] So when I teach The Mom Test, I have everyone try it now. I say, “here’s a little scenario; your job is to interview each other and try to ask good questions,” because it’s a hands-on skill and you’ve got to practice it. And I can lecture about it and I can tell funny stories and people clap and they like it, but then they can’t do it. To learn a hands-on skill, you need to try it now in a safe environment with proper scaffolding. If it’s more about a decision-making process, so let’s call it a mental skill, or wisdom, you know, how do you make a business strategy? Like what’s a strong business model versus a weak one? That’s where the case study challenges are so, so valuable. It allows people to work through this wisdom, decision-making, analysis.

Rob [00:17:55] You have to match the formats. Your formats play two roles. So you want to vary the formats at least twenty minutes. That’s a rough rule of thumb. If you can do it more often, that’s great. But let’s say you do twenty minutes of lecture. You introduce yourself, you point out the fire exits, OK, you’ve burned all of the goodwill in the room. The attention is fading. But as soon as you switch to a different style of teaching, it gives people a little energy uplift. And so you always want to switch formats, you know, every twenty minutes or so, or more. And then if possible, you want to match the formats you’re switching into to the type of content you’re teaching. And with those two simple rules, suddenly your workshops will be incredible.

Rob [00:18:30] Then the only other rule you really need is please do not run for more than two hours without a good break. And the breaks need to be at least 15 minutes. The first thing I do when I’m designing a workshop, say it’s a full-day workshop, I start by putting in the breaks. Because if I start with the content, you fall in love with the content, and then you go, “Oh, I just have to teach that.” The next thing you know, it’s a three-hour grind with no coffee. So you start with the breaks, then you go, OK, a full day, you split it in half with lunch, a nice one-hour lunch. Don’t compromise. Then you split the two pieces. You’ve got now two three-hour chunks on either side of lunch, split each of those with a fifteen-minute coffee break. Put a little buffer on either end, you’ve got your eight-hour workshop day and it’s divided into these 90-minute segments. Then you go, “OK, in those 90-minute segments, every twenty minutes I’m going to need to switch a teaching format, at least. What are my learning outcomes?”.

Rob [00:19:13] Never start with the slides. Always start with what you want your audience to receive and what is the appropriate teaching format to deliver that. And then you kind of cobble that together and you go, “OK.” And then you go, “so I’ve got a lecture chunk here, I’ve got a try it now here, I’ve got a case study here,” let me make the workshop materials. And then finally, now that the workshop’s almost completely designed up to the point I call the skeleton, you go, “OK, I need slide decks, I need handouts, I need et cetera.”.

Rob [00:19:36] So the two mistakes, they start with the content, they start with the sides. So they forget their coffee breaks, which winds people down, they don’t switch formats, et cetera. And then they just end up with too much stuff and then they’re rushing and they’re like, “oh, I just spent eight hours making one hundred slides, I can’t delete them all.” You don’t want to do that. You want to start with the learning outcomes then make like five slides that support exactly what you need your audience to receive. And this is as true for an executive retreat, as it is for a team-building workshop, as it is for educational onboarding, for new members, as it is for a sales workshop where you’re actually educating your customers about why your product or your offering is going to make sense for them. These principles apply pretty widely.

Rob [00:20:10] Online workshops rely on different teaching formats. So you can still do small group discussion, but it’s a lot harder to do try it now, for example. So online you adapt. I feel like the toolkit online is a lot more limited, at least until we get better software to use that really enables this sort of quick format switching.

Sean [00:20:26] I love that. So really, the advice I heard was, don’t start with your content, start with your audience.

Rob [00:20:32] The worst workshops I’ve ever given… I gave one in Russia that was just awful. It was one of the worst, worst sessions of my life. And the reason is that I thought the people in the room were going to be different from who they actually were, because I’d originally agreed to do the workshop for 25 entrepreneurs, but then it got overbooked. And so then they announced that it was overbooked and that attracted the press. And so when I showed up, it was twenty-five entrepreneurs plus 200 reporters, and suddenly none of my exercises made any sense and everything I said people were confused by. They’d even changed my seating chart.

Rob [00:21:05] And suddenly I’m like, “wow, it doesn’t matter how much I know about this topic; you’ve completely removed my ability to deliver a coherent session because you’ve changed the audience and none of my learning outcomes make sense if the audience isn’t who I expected.” And so I always start, like, who’s in the room? And you’ve got to know that. Who’s in the room, what makes this a win for them? What do they already know? What do they already believe? Imagine how boring it is- I’m sure you’ve been to these talks. You show up and it’s like, whatever, how to do business model modeling. And then you’re like, “OK, I’m here, I want to know how to do it.” And then the teacher spends the first two hours explaining why it’s important. You’re like, “I already know why it’s important, I’m here, like, I want to know how to do it.” And they’re like, “yeah, but some people signed up who didn’t know why it was important.” It’s like, that’s your fault. You failed at marketing and you attracted the wrong group to the workshop. You’ve now promised something you’re not delivering. That’s again, it’s an upstream failure. And then once you get into that situation, you’re just like, “all right, I hope we have beer because this is going to be a disaster.”

Sean [00:21:58] What do you think, Matt? You ever been in a bad workshop?

Matt [00:22:01] I have been in bad workshops and I have led workshops. Actually, as you are going through and talking about how to design and everything, I’ve design curriculums in the past for, you know, employee onboarding and stuff like that. And it’s crazy because you go through those steps of creating all the slides the first time through and then you realize how terrible it is. But then you have to pull back and start to think a little bit wider. So it’s cool to hear somebody say it that way, because if you’re in that space and you’re designing, you kind of stumble upon it. But nobody ever really kind of talks through it, if that makes sense.

Rob [00:22:32] It’s the same mistake people make with software and with products. They start by writing code or they start by doing detailed high fidelity mockups. It’s like, no, start with the use case. Start with the goal. Start with the customer, you know. Like otherwise, all this fine-grained work you’re doing, it’s just going to get thrown out later. It applies to any sort of product. The same is true with books, like the stuff I’m doing now with authors for Write Useful Books, it’s like do not start by writing words, start by teaching, start by understanding, like, what your reader is trying to accomplish when they pick up your book. It’s the same principles of product design. Like Mom Test applies it to product, Workshop Survival Guide applies it to education and write useful books applies it to nonfiction, but it is the same principles.

Matt [00:23:09] I’m curious on one thing that you just said. I kind of want to pull one of the threads because you had brought up coding. And I know from your past you were trained as a developer, as a coder, and then kind of worked your way into product development and sales and marketing and stuff like that. So I’m curious what the influence from the coding world has had on how you developed through The Mom Test and through all of your books and your experiences and stuff. It just seems like that has a pretty good sway on kind of perspective. So I’m just curious to get your thoughts on that.

Rob [00:23:40] Well, I certainly, when I give my advice, I’m giving it for technical people primarily. Like The Mom Test, you could describe a sales or user research for introverted technical founders, and then it’s ended up resonating a bit more broadly with product managers and other groups of people. But it’s so helpful to have that clear segment in your head when you’re designing any sort of product, a book included. Because otherwise, how do you know what they already know? How do you know what they already believe? Which anecdote or example or case study should you use? All these little questions, they’re the difference between something that feels really tight and compelling and engaging to read or to use or to experience and something that feels real rough around the edges. So that’s helpful in programming, it’s like, you’re constantly trying to break what you’re making, right? You type a few words of code, you compile it, you look for the server errors. You’re looking at what it looks like. You’re trying it out. You have people use it, you want them to break it. I think that’s a very healthy attitude to bring everywhere else.

Rob [00:24:32] And, I mean, most product designers know this by now, but certainly, with authors, they’re just a disaster. They’ll spend a full year writing a beautiful manuscript before they try to show it to anyone. And then the person’s like, “I liked it,” and they’re like, “great, it’s ready to publish,” and then they go, “I don’t know why I didn’t sell many copies.” You know, it’s like, well… You know, it’s like, it’s the four-hour educational experience, you’ve got to test that, just like you would with a product, just like you would with anything you’re building.

Sean [00:24:59] Yeah. Another quote from The Mom Test that what you said reminded me of: “some problems don’t actually matter even if they technically exist.” And you don’t really know if the problem is real until you get out in the market and you learn from it.

Rob [00:25:11] There’s so much interesting data in nonconsumption. Especially with aspirational problems like security or privacy or saving the environment, political injustice, if you run an interview and say, “Hey, do you think political injustice matters?” Like one hundred percent of people will say, “yes, a huge priority for our business, we need equality,” whatever, something that their press team told them. And then you go, “oh, so what are you doing about it?” And they’re like, “eh…” You know, they’ll give you some sort of fluff. But if you poke at it, it’s like, OK, they’re doing nothing. Same deal with email security: “security is very important, we care about our customers.” Like, “oh, how do you deal with it now? What else have you tried, what’s working, what’s not?” This is a hard conversation because people feel like they’re being attacked or undermined or they’re embarrassed, but you only need a small subset of people who are on your side of the table to be representative of the rest of the industry. And you’ll quickly learn that it’s a problem in air quotes. It’s not a problem they’re actually motivated to invest the time and energy in solving.

Sean [00:26:05] Or solving it another way or whatever.

Rob [00:26:08] They’re solving it by ignoring it, yeah.

Sean [00:26:09] Or that, yeah. Back to workshops, you had some great advice about, you know, there’s always one person in the room that’s just sitting there ready to stump the chump, you know, to bring the whole thing down. It’s just that character. And you had some great advice on dealing with the negative energy characters in the workshop room. So I want to hear about that.

Rob [00:26:30] There’s different types. I can’t remember the full list. When I wrote that, I was pretty mad. I was thinking about every person who’d ever messed up one of my workshops. And I eventually realized that, you know, there is a way to handle each of these categories and to do so in a quite polite and respectful and low-drama way. The most common, by far, and what you’ll get the most, especially in professional workshops, is someone in the room who is an expert and really knows what you’re teaching. And they didn’t show up by choice. They were forced to show up by their boss or by their team or whoever. And they feel like they’re being lectured down to or they’re being taught something they already know. And they will look for any little opportunity to nitpick and to provide a counterexample and to disprove what you’re saying as a generalization with a specific. It’s pretty difficult to deal with.

Rob [00:27:15] And the way to handle it is so easy and it’s so clean. As soon as you realize that you’ve got an expert in the room, you start including them in your teaching. You say, I mean, “Hey, Matt, I mean, you know more about this than anyone here. Like, do you have different experiences? How do you approach it on your team?” And suddenly Matt is like, “whoa, I’m not being taught down to, I’m being elevated as an expert.” And suddenly your detractor becomes your biggest supporter. And he’s like, “oh, yeah, what Rob’s saying is really true most of the time, but what I’ve seen in some situations is this.” “Oh, thanks, Matt, like I really appreciate it.” And then you give them a, you know… It’s stuff like this and that solves ninety-five percent of professional workshop problems. Just the detractor is actually a secret expert. You can sometimes figure this out if you do a little bit of pre-event networking, but it’s not always possible. And then there’s a few others, you know, but I don’t know. Were there any in particular that you wanted to discuss, Sean?

Sean [00:28:04] The bore was one, but I call bikeshedding. You know, the story about when they were building the first nuclear plant that everybody got so focused on the paint color of the bike shed that they delayed the whole project. And you often have that person in the room that just wants to go into the weeds on this one specific issue and derail that. It’s not even intentional, you know.

Rob [00:28:24] Yeah. And often they’ll ask another version, they’ll ask incredibly specific questions that could only possibly apply to themselves. And so if you properly handle the question, you’re boring everyone else in the room to death and killing your energy curve and your timelines, then you run late. So the solution to all of these is you go, you go, “super interesting question, sounds like it’s a bit specific to you, let’s talk about it at the lunch break or let’s talk about it after the session. I’ll come to you straight away.” And you make that time, you try to honor that promise as much as you’re able, and then every other question they ask because they’ll ask a few more until they’ve learned, you go, “again, great question, let’s talk about that when we chat at lunch.” And you just push it out to that future date and then that gives you a polite way to deal with it, which doesn’t create a big drama or hostility. And, you know, everyone’s happy and then you can move on with what the rest of the audience needs.

Sean [00:29:10] For sure. I think we could do a whole episode on just workshopping and this sort of thing. That would be kind of neat.

Matt [00:29:16] I agree.

Rob [00:29:17] These were hard-won lessons, right? Because much like with The Mom Test, I learned and then wrote this book off of making every mistake in it. And, you know, afterward, I had quite a thoughtful teaching team alongside me. Also one of the people who helped me figure out the ideas in The Mom Test, Salim Virani, after every workshop we’d go, “oh, that went really badly,” and then we’d do kind of our root cause analysis and our five why. It was like, “I think we lost this section of the audience here and this person got really mad about this, like, what can we try differently next time?” And we kind of first-principled our way.

Rob [00:29:44] Because all of the knowledge I could find about workshops wasn’t what I wanted. It was about being charismatic or doing icebreakers or clever ways to design your slides. I’m like, “this is tactical and superficial, this doesn’t get to the root of the issue.” Like, the root of product design is, do people care? Like, do they really have the problem, and do they want a solution? Right. Or can you make something so joyfully better than what they already have that they’re going to gladly ignore the switching costs and hop over? The foundation of education is like, do the learning outcomes matter and can I choose the formats and, anyway, all the stuff we just said. And so I felt like I kind of had to figure it out myself because no one else wrote it in the way that made sense to me. Everyone’s focused on the polish, like the top layer, and they forget about the foundations.

Sean [00:30:25] Focus on the content.

Rob [00:30:26] Exactly, exactly.

Sean [00:30:28] Right.

Matt [00:30:29] I love to focus on like education as a product. Like that’s just something that is so different in my mind and thinking of it from a different perspective. But it makes so much sense when you think about it that way, and especially with how you’ve kind of laid out all of the thoughts around the design and figuring out the best way to approach and not focusing so much on polish. That just resonates really well, just with, I was a trainer for a very long time, so a lot of that stuff kind of hits very close to home. But that’s awesome. I want to switch gears just a little bit, though, Rob. It’s a question that we tend to ask everybody who comes on to the podcast, but how would you define innovation?

Rob [00:31:05] I don’t know and I’m not sure it’s useful necessarily to try to pin down an exact academic answer. For me, the point of doing it is to build the life I want and to push the value I want into the world. So like with books, for example, what I’m doing now with Write Useful Books, whenever someone writes a nonfiction book or a business book, they’re doing it because they really care and because they believe they have something to share and they’re investing somewhere between 500 and 2000 hours, valuable hours, right, into the creation of this book. And then their books fail, almost all of them. And to me, that sucks and I feel like I have a way to stop that from happening with the process and the tools, anyways, all this stuff.

Rob [00:31:39] And so it’s like, “OK, well, that’s valuable to me and I want to get that out there and I want to get it out there at scale to have this positive impact.” And so then it’s like, “OK, well, how do I do that?” Well, I’m going to need a value proposition and I’m going to need a distribution channel and I’m going to need to package it into a product that people take seriously and it’s going to need to fit into their workflow so I’m going to need to understand that workflow.

Rob [00:31:58] But I’m not an optimizer, and I always give this disclaimer. I’m not trying to build the biggest product possible. I’m not at the mercy of a board or stockholders. I’m trying to build a good life for me and my family and to be proud of the way I spend my time. And so I have a lot of flexibility there and I’m allowed to be suboptimal and I take that luxury very seriously. Like, I want to be good enough, right. And like five years ago, I hit the financial independence point where my, like, passive income from stuff was greater than my monthly expenses. And so then I’m like, “OK, great.” I spent two years learning to sail. I brought my boat from London to the Mediterranean. I moved to Barcelona. But then I’m like, “OK, I’m a little bored with being a layabout, let’s get back to work.” It’s like, what do I care about now? Who do I want to hang out with? Let’s choose them as the customers and figure out how to serve them. So that’s what it is to me. Like it’s just a toolkit for scaling the things you care about.

Sean [00:32:44] Allow yourself to be suboptimal. I love that. Alright, last question to wrap up. In the product space, any book recommendations going back into your history? Like what do you think is the best book you’ve ever read that product leaders should think about reading, obviously, other than your own, that I’ve already pitched and promoted twice for you.

Rob [00:33:01] For processes and hiring, the E-Myth Revisited is exceptional. It was written in the 80s by Michael Gerber and it’s aimed toward small retail businesses like bakeries and independent hotels. But the lessons around building a process and onboarding staff and not expecting people to know how to do things that you don’t know how to do, but rather it’s your job as the product owner or the business owner to figure out those. Super fascinating viewpoint. It doesn’t apply to all technical businesses or roles, but there’s some incredibly valuable ideas in there that I think the tech world has forgotten about.

Rob [00:33:32] I also really like Good Strategy Bad Strategy by Richard Rumelt. And strategy is one of these fluffy words that means everything to everyone. And he really takes apart what strategy isn’t so that when someone goes, “our strategy is to grow,” you go, “that’s not a strategy, that’s a goal.” Like, you know, a strategy is an accurate analysis of our current situation, like a set of guiding principles about what we need to do differently and then a few practical steps to get us started. And it’s a lovely book, very pleasant to read.

Rob [00:34:00] And then the last one, again, not a direct product book, but relevant to everyone in the space, is Never Split The Difference by Chris Voss. The subtitle is Negotiating As If Your Life Depends On It. He was the lead hostage negotiator for the FBI, and I almost feel like it’s got the same heart and spirit as The Mom Test, which is like how do you get to the truth in an empathetic way and how do you control the conversation with your framing and the context and the way you ask the questions? And obviously, he’s applying it to life or death negotiations. But as soon as I read it, there’s relatively few books that I would have paid one hundred thousand dollars for after reading, or let’s say ten thousand dollars, that’s still a lot for a book, but certainly, that’s one of them. And I only read it a year ago and it’s already added well over that to my take home. And I would have said the same E-Myth Revisited, both exceptional.

Sean [00:34:48] Great recommendations. Well, thank you, Rob. This has been a fantastic interview. I think we’ve got a lot of great nuggets in here to share with the audience and I appreciate your time.

Rob [00:34:57] Thank you for having me. It’s been fun.

Matt [00:34:58] Thanks a bunch, Rob.

Paul [00:35:02] Well, that’s it for today. In line with our goals of transparency and listening, we really want to hear from you. Sean and I are committed to reading every piece of feedback that we get. So please leave a comment or a rating wherever you’re listening to this podcast. Not only does it help us continue to improve, but it also helps the show climb up the rankings so that we can help other listeners move, touch, and inspire the world, just like you’re doing. Thanks, everyone. We’ll see you next episode.

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