Unorthodox PM tips: Automating user insights, unselling candidates, decision logs, more | Kevin Yien

Kevin Yien: The PM job can become a little too internal, influencing my stakeholders and getting alignment and all these things. But if you can’t sell or support your own product, I don’t trust you to build the product.

Podcast Episode Introduction

Lenny Rachitsky: You think every PM should keep a decision log?

Kevin Yien: We all talk about product sense. To me, it’s just a fancy way of saying you can make good decisions with insufficient data. PMs need as many reps as possible in making decisions, documenting the rationale behind those decisions, and then crucially seeing the outcome of them.

Starting With the Avatar

Lenny Rachitsky: We have a lot of interesting approaches to hiring, including this idea of a unsell email.

Kevin Yien: When you get to offer stage, I send an email and I say all the terrible things that are probably going to reinforce their fears. If you can tell them that upfront and they can read that whole email and still be equally excited to join you, find yourself a A+ hire.

Why Not Start Directly in PM

Lenny Rachitsky: I’m curious if you found any interesting uses of AI in your work.

Kevin Yien: We are not even beneath the dust on the surface when it comes to what’s going to change.

Where to Start as a PM

Lenny Rachitsky: Today, my guest is Kevin Yien. Kevin leads product for merchant experiences at Stripe. Before that, he built the restaurant business and the ecosystem teams at Square, and most recently was head of product and design at Mutiny. He also makes ice cream and, as you’ll hear in there conversation, was a pretty competitive eater for some part of his life.

In our conversation, Kevin shares a ton of unique and insightful perspectives on how to be a successful product manager, including how to get into product management, how to improve your relationship with your engineers and designers, bunch of advice on hiring, why you should keep a decision log, how to automate your customer research, plus a ton of really powerful stories around failure and AI and career.

This episode is for anyone looking to become a better leader, thinker, and builder of products. If you enjoy this podcast, don’t forget to subscribe and follow in your favorite podcasting app or YouTube. It’s the best way to avoid missing feature episodes, and it helps the podcast tremendously. With that, I bring you Kevin Yien.

Kevin, thank you so much for being here and welcome to the podcast.

Kevin Yien: Thanks, Lenny. I am humbled to be here.

Importance of Writing for PMs

Lenny Rachitsky: I’ve been a big fan of yours from afar. I’ve been following you on Twitter for a long time. You have a very distinct profile photo that I feel like you maybe haven’t changed for a long time. How long have you had this profile?

How to Become a Great Writer

Kevin Yien: Oh gosh, probably 2011 or 2012. The story behind that is I was inspired actually by Chris Dixon’s avatar at the time and I wanted something really similar to it, but I couldn’t figure out how to. Luckily, I was dating a designer at the time, and so she made me that sort of custom pick that has been my profile since then, and she’s now my wife.

Collaborating With Engineers and Designers

Lenny Rachitsky: Oh my god. Funny enough, I had a startup idea once where it’s like a profile picture as a service business where there’s these three tiers where it’s like one has automated, one has someone illustrates, and one is a professional photo. It feels like everyone profile photos are so important.

Defining the Problem Space Boundaries

Kevin Yien: True.

Obsessing Over the Final Deliverable

Lenny Rachitsky: But I never follow through. Probably not a good business anyway.

A Square Restaurant POS Story

Kevin Yien: Yeah, but a good idea, a good tool.

Making Time for What Matters

Lenny Rachitsky: Good idea. Thank you. Thank you for making me feel better.

I’ve been looking forward to this conversation for a long time. As I said, I’ve been a big fan of yours for a long time. Something that I’ve noticed about you is you have a lot of really unique perspectives on a lot of different things, and in particular, product management, how to be successful as a PM, how to get into product management, things like that. So I thought it’d be fun to start there talking through some of these things that I’ve heard you talk about and then get into some very tactical stuff that you found to be useful in your product management career.

The first thing that I’ve heard you talk about is that you discourage people from going straight into product management. If they want to become product managers, you encourage them to start somewhere else first. Why is that? Where do you think people should start? Talk about this insight that you’ve had.

Kevin Yien: Yeah, so follow me on the detour to science world temporarily. If we all remember high school science classes, there was this concept of potential and kinetic energy. There’s so many different definitions for product management, but the one that I have come to myself that I really like is, when you are building a product, you have this team, engineers, designers, so much potential. The purpose of product management, not the person, but the practice, is to convert that potential into as much realized value for someone as possible, right? Minimum loss. When you’re just getting started with a new product, the people that should be doing that are the people who are building it. That’s an engineer, that’s a designer, that’s a sales person or a support person. They’re the front line of the smallest loop possible to get something going, and it’s through those practices that I think you’re able to get the most exposure to what it takes to build a good product.

And then from there, that’s your foundation. That’s the unique perspective that you bring and allows you then to actually take on a “role” of product manager in a good, unique, insightful way. That’s sort of like the foundation. There’s a lot more to unpack behind that comparison, but that’s where it comes from.

Setting Boundaries: Creativity Through Constraints

Lenny Rachitsky: I love that. I’d love to unpack it further.

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I’m excited to chat with Christina Gilbert, the founder of OneSchema, one of our longtime podcast sponsors. Hi, Christina.

Christina: Yes, thank you for having me on, Lenny.

The Tuning Fork Strategy and Silent Reading

Lenny Rachitsky: What is the latest with OneSchema? I know you now work with some of my favorite companies like Ramp, Vanta, Scale, and Watershed. I heard that you just launched a new product to help product teams import CSVs from especially tricky systems like ERPs.

Christina: Yes, so we just launched OneSchema FileFeeds, which allows you to build an integration with any system in 15 minutes as long as you can export a CSV to an SFTP folder. We see our customers all the time getting stuck with hacks and workarounds. And the product teams that we work with don’t have to turn down prospects because their systems are too hard to integrate with. We allow our customers to offer thousands of integrations without involving their engineering team at all.

Lenny Rachitsky: I can tell you that if my team had to build integrations like this, how nice would it be to be able to take this off my roadmap and instead use something like OneSchema and not just to build it but also to maintain it forever.

Christina: Absolutely, Lenny. We’ve heard so many four stories of multi-day outages from even just a handful of bad records. We have laser-focused on integration reliability to help teams end all of those distractions that come up with integrations. We have a built-in validation layer that stops any bad data from entering your system, and OneSchema will notify your team immediately of any data that looks incorrect.

Lenny Rachitsky: I know that importing incorrect data can cause all kinds of pain for your customers and quickly lose their trust. Christina, thank you for joining us. If you want to learn more, head on over to oneschema.co. That’s oneschema.co.

Every PM has their definition of what is product management, and I have one that I’m trying to find exactly what I wrote, but essentially, it’s to marshal the resources of your team to solve customer problems and drive business impact most efficiently, something like that. And I feel like it’s very aligned with your perspective, but I really love this view of it’s unlocking the potential energy of the team. Not just marshaling the resources of a team, but it’s there, and your job is to maximize their effort. And this is why when people say, “I hate product managers. I don’t want any product managers at my team. We don’t need product managers here,” I feel like that’s often because you’ve had a bad PM. Good PMs make you better and make your life better, allow you to do the work you want to do and they take all the stuff you don’t want to do, make sure the stuff you’re doing is worthwhile.

Is there anything more you want to add along those lines?

Tactical Tip: Decision Logs

Kevin Yien: To elaborate on that, I think the broader point is that truly not every team needs a product manager, but the activities, the outcome that one would drive needs to get done no matter what. And in some cases, this is why the prototypical companies that everyone references when they say, “They never had product managers, look at how successful they are,” they’re all building for themselves. Stripe, Twilio, Figma, designers for designers, engineers for engineers. When you are the customer, why the heck do you need someone else to help do the things that let you make decisions on what to build? But if you are not the customer, if you’re working in a particularly complex space, if there’s something that you, as the person that could build the product, feel you don’t have, that’s when you can essentially delegate that responsibility to someone else to say, “Hey, let me do the things I’m really good at and you do something that I need to get my job done.”

So it’s that sort of relationship that I think is often missing in the discourse. I think it would alleviate a lot of the, “We don’t want PMs. PM is useless” or, “PM’s one of the best thing since [inaudible 00:09:52],” which they’re not. It’s just a manifestation of that problem.

Simulating Others’ Decisions

Lenny Rachitsky: Yeah. Just to build on that, we’re going on a tangent, but I think that’s really interesting. I think there’s another element of that, SNAP actually is another example where they waited, I think, until they had 200 people before they hired their first PM. To me, that’s an example of other people were doing the PM job. As you said, there’s PM activity, someone’s doing them, lining people, prioritizing, making sure things are clear, making sure people aren’t surprised, all these things PMs do. Someone’s doing that, and my feeling is like, “Okay, your designers may love doing that, great. Let them do it.” If your engineers that have a lot of product sense may want to do that, great.

But there’s some point they either is like, “Forget it. I just want to code. I want to build that. I want to be sitting around in meetings all day,” or they just aren’t as good as things are scaling. And so it’s kind of like, if your engineers, designers want to do it and are good at it, great. You don’t need PMs for a long time. Oftentimes they’re not good at it or they don’t want to be sitting in doing all these PM things.

Kevin Yien: Yep, precisely.

The Specific Format for Logs

Lenny Rachitsky: Okay, so going back to the question of… So your advice is don’t go straight into product management if you want to become a great PM. Where do you think people should start if they can? What are some options you recommend?

Kevin Yien: The best way to think about this, in my opinion, is who were the people that you would be taking the PM responsibilities from and then do those jobs? And so for me, the sort of foundational three are going to be engineer, designer or salesperson. I think sales also gets not a bad rep, but a misrepresented reputation in tech where all they care about is quota, it’s just about numbers, et cetera. In reality, the best salespeople are the best listeners, the best people at understanding the problem that the customer is having and then translating that into what you can do for them. And so if you get really good at having those calls, getting told no a lot, and being able to translate that, I mean, why would you not want to start there and then eventually move into something like product? So that’s the foundational three for me.

Decision Logs and Interviews

Lenny Rachitsky: So your advice is essentially if you want to be a PM, start as a designer or an engineer or a salesperson. I was an engineer, so this is exactly the path I went on. And I think there’s an element of you start there and then you realize you’re never going to be as amazing as the other people at that role and you’re like, “Okay, maybe I should explore this other thing,” because I was like, “I’m never going to be an amazing engineer. I’m good enough.”

The Unselling Email

Kevin Yien: Totally.

Lenny Rachitsky: I’m like, “I’m pretty good at this other stuff. Let’s explore that.”

Investment and Responsibility in Hiring

Kevin Yien: The one thing that I might tack on there, because this could lead to a negative perception, is, “Well, I’m never going to be a world-class engineer, world-class designer or et cetera, and so let me settle for being a PM.” That could be the conclusion you arrive at, but I think a better way of framing it is, “I’m okay at those things. I’m potentially world-class at this other thing. Let me see what it feels like to double down on this area.”

Automating User Research

Lenny Rachitsky: Absolutely.

Methods to Automate User Interviews

Kevin Yien: And I think that’s just a good framing.

Lenny Rachitsky: Okay, so let’s talk about another insight and piece of advice that you have, is that you think that great PMs need to be great writers. I think a lot of people don’t necessarily think this. I think people may probably think, “If I’m an okay writer, I can probably be really successful PM.” Talk about why you think it’s so important to be a really great writer to be a really great PM.

No Excuses for Automation Difficulty

Kevin Yien: It’s actually shocking for me to hear that this isn’t commonplace sort of acceptance, but the place that this comes from for me is, writing is clarity at scale, and a key component to a PM’s job is creating clarity both internally and externally, but it is both sides of that that I think often get lost. A lot of times the PM job can become a little too internal, and it’s about influencing my stakeholders and getting alignment and all these things. Don’t get me wrong, all that’s very important. You should write your PRDs, they should be super crisp, they should articulate things really well, but I’m not saying that every PM needs to be a marketer or a world-class copywriter, but you should be able to write really compelling messaging in the voice of the person that you’re trying to serve. And I’m working backwards from the beliefs that, if you can’t sell or support your own product, I don’t trust you to build the product. And so that’s where I think writing is the foundational component there.

The True Value of Customer Conversations

Lenny Rachitsky: There’s a few quotes I say often on this podcast just because they always come to mind. One is by Joan Didion who said that, “I don’t know what I think until I’ve written it down.” And that’s what I find with writing where I need to actually write it down for me to really understand what the heck I’m thinking to really crystallize it.

The AI Corner

Kevin Yien: Yeah, and I think writing is, it’s both a mechanism for translating what you’re trying to think into that thought into what you’re actually trying to do, but then it needs additional revs to be properly consumed by everyone else. And that’s I think the really hard part that a lot of folks don’t do the extra mile effort to take on.

Lenny Rachitsky: And this to your earlier point of a job of PM is to unlock this potential energy of your team, of the various resources you have and obviously having everyone aligned behind a very, like, “This is what we are doing and everyone understanding it” and it being very clear is really powerful there.

Okay. So this begs the question, how does one become a great writer? What helped you become a better writer? How do you feel about your ability to write at this point?

AI Corner: A Midjourney Story

Kevin Yien: Oh man.

Failure Corner: Layoffs and Rebuilding Confidence

Lenny Rachitsky: Any advise on becoming better?

Kevin Yien: I’ll start with a slightly cheeky comment, which is, I think some of this is changing with the advent of large language models and the ability to actually just mimic someone else’s tone. But I take inspiration from the camp of Anthony Bourdain, and he has, I’m going to butcher the exact quote but it’s something like, “If you want to know how to make good food, you have to eat a lot of food, and you have to be willing to have a bad meal every now and again.” And so for me, good writing comes from consuming as much good writing as possible. Sometimes you’ll read something and say, “That was actually absolute fresh.” But that’s okay, you have to be willing to take on some of that stuff. But the more you index towards developing your own taste for what you think is good by consuming others, then you can shift into producing your own and then comparing them and riffing it off other people. So I think that’s sort of the cycle that I’ve gone through.

The Company Habitat

Lenny Rachitsky: I have a friend who’s a very good writer and a poet and helped me develop my writing early on, Vanessa, and she said exactly the same thing. Just to become a better writer, read beautiful writing, and it just kind of infuses you or your brain. In your experience, is there anything you read, anything you found really effective? Anything that you think influenced the way you write or think that people can check out?

Top Book Recommendations

Kevin Yien: I explicitly do not mean read a bunch of other PM artifacts. You’re not going to become a better writer by reading PRDs or whatever it is or support articles. It needs to be writing that compels. That’s the theme I would go back to because that’s what you’re trying to do at the end of the day.

And when I say compels, I mean it pushes you to action. Because if you read something and you’re like, “Oh, that’s interesting,” that’s not enough. You need to be able to give someone something that then allows them to do something differently. And so the things for me that have been best… Obviously there’s all the Paul Graham essays, I think his writing is very succinct, very clear, that’s not novel. I learned a lot by finding specific voices back in the day on Twitter, and it wasn’t always what they were posting on Twitter, but if they wrote an essay or a post, that would be their crispus thinking. And so you can use these broadcast channels to find where their golden nuggets are, but then spend time with those instead and don’t worry about all the additional noise that comes with it.

Movie and TV Recommendations

Lenny Rachitsky: Paul Graham actually, you mentioned him, he has a great piece on how to become a good, that we’ll link to, where basically his advice is, write the way you talk. Just keep it really simple and really regular. And so we’ll link to that. Is there anything else along these lines of writing that you’d recommend for folks that are like, “Okay, I need to become a great writer. How do I do this?”?

Kevin Yien: Actually along the lines of write how you talk, there’s this concept of cadence that I think is really important when it comes to internal writing. There’s probably some very good article about this, but it’s the idea that if you only write in a monotonous cadence, either all really short sentences or all really long sentences, then your brain just tunes out eventually. And so you have to interrupt the pattern intentionally, and so you go short-long, long-short, whatever it is, but there’s a few various specific things that you can do that allow someone to just roll through a post or something when you write that way.

Great Products Found Recently

Lenny Rachitsky: Along those lines, there’s a book that I just found to make sure I had the right title called Several Short Sentences About Writing that is really helpful along these lines. And the whole book is very short sentences and it teaches you to write very short sentences because once you’re good at that, you can get better writing longer sentences. And so we’ll link to that too. It’s like a really good book that I have two copies around my house that I kind of poke at sometimes.

My Life Motto

Kevin Yien: Nice. I’ll have [inaudible 00:19:09] too.

Lenny Rachitsky: Okay. Another area that you have a really clever insight into is how the PM role fits with engineering design. We’ve talked about this a little bit, but you have a really clever way of just thinking about how these roles interact and who’s responsible for what. Talk about that.

Competitive Eating Experience

Kevin Yien: So this description came from writing PRDs at Square. I think there was a lot of confusion from my team specifically when I joined them. For what it’s worth, it was new product line, three engineers, three designers, there was nothing but a slide deck.

Lenny Rachitsky: Three engineers and three designers?

About My Personal Website

Kevin Yien: The best ratio ever. This is a whole other thing. Most people, I would say, under invest in design, point-blank. When you get to a certain scale, maybe things change, but truly I don’t think most teams have experienced what it feels like to have a really high design ratio and what that actually does to the quality of the work and the quality of the thinking. So shout out to designers. We need more, is the short version. And I would rather hire an incremental designer than PM almost any day of the week.

Lenny Rachitsky: Wow. I’ve never experienced this ratio. Incredible.

The Power of Kindness

Kevin Yien: Yes, I was very lucky. Shout out to Bruce Bell, who was my manager at the time, who was an ex designer, at the time, GM, and declared that starting ratio.

So anyways, with that setup, they all had sort of an opinion. They had seen PRDs in the past, they weren’t quite sure what the purpose of it actually was because they had designs already. They had something to start from. And when I came in and talked to everyone and figured out where we needed to be in a year’s time, I was like, “Okay, here’s how I think it. Let me know if you agree.” And this is a whole other concept, which is, the best way to get feedback from people is not by asking what they think, but to put something concrete in front of them and then have them react to it, right? So chewing fork.

And so my description is, PM should be doing everything in their power to draw the perimeter of the space, of the problem space. And it’s within that, eng, design, everyone else that you’re working with, they can go as crazy as they want, push up against the bounds and it’s fill the box to its maximum capacity, but you’ve now applied the constraints that allow you to actually have productive conversations.

On the other end of the spectrum though, I think there’s a lot of folks who think, “Oh, PMs are just strategy high in the clouds. All they do is kick things off.” You need to be obsessed about the final deliverable and whether or not value is actually getting to the customer. I have a really trite example of this if you want to go down it.

Lenny Rachitsky: Please.

Kevin Yien: But the key point I want to make is, I think it is tempting when we think about engineering product and design to draw these really clear swim lanes and say, “You do X. I do Y. Don’t tread on my area.” But you need these murky overlaps in order to build something really good.

And so even if the engineers are going to build a better product than you and the designers are going to design something better than you, you need to come with a strong opinion and you need to do the legwork to get their trust so they actually care about your opinion in the first place.

So time for a mini story. So Square, we’re building a point of sale for restaurants. If you’ve ever seen one of these in a restaurant, there’s this sort of grid of tiles that they tap to enter your order when you’re sitting down for dinner. We were developing one, and there’s this concept of a menu group. So it’s a little box, you tap on it and then it pops the screen in so you go to the next level of the hierarchy. So example would be you have a wine button, you tap it, and you see your reds, whites, et cetera.

If you think about the people that we were trying to serve, there’s the restaurants that were coming from a really old legacy system. And if you’ve seen a bartender tap on one of these, I mean it is muscle memory to the max. They’re not even looking at the thing and just punching in the order blindfolded, and it’s rapid fast.

On the other hand, you have people who are entering the workforce the first time, they’ve never used a point of sale. And so we have to serve both of these equally. Well, how do you deal with that level of speed but also the ease of use that anyone can learn it for the first time? And so there was this interaction that we really cared about, which was, when you tap on a menu group, what’s the animation to pop you into that next level? This seems like such a small thing, but it made the difference in how easy it was to adopt for a lot of the restaurants.

And so a designer and myself spent literally an entire week just fine-tuning how many milliseconds it would take to pop in and out so that it felt right. And we actually brought in servers and bartenders to play with the prototypes we had on iPads and be like, “Here’s an order. Pop it in.” And we would see where they would sort of flinch or hesitate because the animation was too slow and they thought, “I can’t tap it yet,” or something related to that.

And so it’s easy, I think, for a PM to say, “That’s not my responsibility. I define the requirements. Have a menu group that goes to the next level, design or engineer, figure it out.” No way. That’s fully on you, and you better be involved in those details.

Lenny Rachitsky: I love this. There’s two directions I want to go. So there’s the drawing the perimeter, and then there’s this paying attention to the final deliverable and keeping the borrow really high, which I love and I totally agree with both.

In terms of this animation, people hearing this, that our PMs are going to be like, “How do you have time to spend a week on animation for one little product? I have so much to do. I get to hit some goals, drive some numbers. I have people waiting for me.” Maybe because Square is like this, once you deploy, it’s harder to change and it’s like a big deal to ship. But I’m curious if you have any advice or things you’ve learned about how to create space for that sort of thing to create time to spend a week on this animation? Or was it just obvious to everyone, “We need to spend as much time as we can”? Top down, everyone knew.

Kevin Yien: I definitely don’t think it was obvious to everyone, and I can definitely say that because we were given a pretty strict deadline that we needed to launch by and I pushed it out three times. That’s not because of this one animation, but it’s because of a series of decisions where we said, “This is what we believe we need to ship, and this matters much more than hitting some artificial external GA date.”

There’s this other aspect that I think PMs like to feel good about how busy they are and they’re like, “I’m involved in so many processes and I have to talk to this person and talk to that person.” All that might be true, but I think there needs to be a calibration or at least a spring-cleaning of, “What’s everything I’m doing?” and how much do these things actually matter to getting value to a customer. Because as a company gets bigger, as teams get more complex, it’s very easy and natural to spend more time on things that are internally-focused and not externally-focused. I think we just all have to have sensitive antenna to that so that we don’t fall prey to, “Well, the way that my job is described is to do these things,” but really it’s the outcome again of put something in a customer’s hands that’s also a problem, and it’s amazing.

Lenny Rachitsky: Reminds me of your now colleague Jeff Weinstein’s advice he got from one of the Coulsons where they came to him and they’re like, “You’re world-class at doing the second and third most important things and you’re not focusing on the most important thing because it’s so hard, and that’s something you need to work on.”

Kevin Yien: Totally. I will say so one on that, the CEO at Mutiny, Charlie, she always repeated to me nonstop, “Keep the main thing the main thing” and would just say it ad nauseum, and I’m really glad that she did. The one excuse I don’t want to give folks is, as you progress in your career, you have to walk and chew gum at the same time. You can’t say, “Oh, I’m only focused on this thing over here, so other folks handle that.” You do have to figure out how to do a little bit more at the same time, but prioritization does play a factor.

Lenny Rachitsky: There’s a framework [inaudible 00:27:27] suggested that I really like, the LNO framework. I forget exactly what the LNO stands for, but leverage something something. And we’ll link to it in the show notes that gives you some advice on how to prioritize your time based on the stuff.

Kevin Yien: Totally.

Lenny Rachitsky: Okay. So I guess in the case of pushing back to create space, this was just you as a product leader recognizing, “This is really important to get right. I will convince people we need to make more time for that.”

Kevin Yien: I don’t want to make it seem like it was me against everyone because that was definitely not the case. I think the starting engineers and designers on that team really cared about the quality of what they built too. That’s a pretty structural DNA for a team as well. If you don’t start with that, and as a comparison, you have a team that really prides themselves on shipping fast and meeting deadlines really prescriptively, you might end up in a different world or your role as a PM might be a little bit more challenging if you want to push on this stuff. So I do think you have to take into account what is the DNA of the team. And then can you exploit that? Which I was able to do. Or do you actually have some change management to put into effect if you believe that it’s worthwhile?

Lenny Rachitsky: Let’s go back to the perimeter, drawing the perimeter concept to make that a little more real for people. So your advice here is the role of a PM, part of your main job, especially when it comes to engineers and design is to draw the perimeter for the team. Can you make that a little more real? What’s an example of that maybe from something you worked on? What does that look like?

Kevin Yien: Totally. The best word to describe the perimeter is just constraints. At the end of the day, you should be adding as many constraints as reasonable in order to let engineers and designers come up with the most creative solutions for whatever you’re trying to do.

And so again, if we just stay focused on this point of sale example, one constraint would be, “Who the hell are we serving? Are we trying to go after sit-down restaurants that are serving five different courses and have a 200 item wine list? Or are we trying to serve the taco truck?” Those will lead to very different spaces. And if you leave both on the table, the lack of that constraint makes designing a good solution that much harder, that there instances where you actually can’t apply that many constraints. But I bet that if you push on enough different axes, you eventually scope it down to a point where it feels really good for the team. It’s just about how do you remove decisions, right? Because this I think is maybe a trite phrase, but the best decision is no decision. If you don’t even have to think about the decision, the team is that much more effective.

Lenny Rachitsky: So yo give people a few maybe even pointers of, “I need to create more constraints maybe for my team to help them go crazy, but within this box that we all agree on,” so you mentioned make sure the user’s clear of who you’re designing for. Is there anything else, just thinking about maybe the PRD someone’s trying to write to help create this constraint? What other maybe bullet points, sections would you imagine or do you find useful to add?

Kevin Yien: So beyond customer segment/like-what-their-specific-role is, I think another one would be, we can loosely call it, jobs to be done, even though I know that’s becoming an increasingly loaded term.

Lenny Rachitsky: Yeah, it’s great.

Kevin Yien: But what’s the thing they’re trying to do and how many different pathways are you willing to entertain around it? That’s another one that I would think about. Depending on what you’re building, there’s availability. So do you care about desktop web, mobile web, native mobile, et cetera? And maybe another one to think through just as an example would be, this is probably getting closer to what a lot of people think about in terms of principles, but what are the things that you want to be known for when you ship a product? One example there might be speed. And so if you say speed is more important than consistency of data, that’s a huge tradeoff and constraint that you can give the team.” Oh my god, if an engineer hears I don’t need real time consistency of data, I can do so much cool stuff and easily accomplish that speed thing.” And so that’s just a very technical example maybe.

Lenny Rachitsky: Awesome. Okay, I’m glad I followed up on that. There’s a couple more things you mentioned that I want to come back to real quick. The first is this tuning fork idea. I completely agree, this point you made, that the best way to get feedback from your team is to take a first pass at it, and here’s a rough quick draft. I find with design, especially if you design something ugly, designers are often like, “Let me make that better. We can’t stand this thing.” Is there anything else you want to add there? Just this idea of tuning fork as a feedback strategy.

Kevin Yien: Okay, there’s two areas we can go deeper on here. One is in how you get the feedback. So this is definitely a Square-ism, I think it was probably adopted from Amazon, which is around the silent read of documents. When you are all so busy and someone’s like, “I wrote a doc,” you send it into the Slack ecosystem and everyone goes, “Please give feedback.” You have so much going on… You’ll be lucky to maybe get a response. Maybe there’s one or two people that chime in.

And so even though we hate meetings and we love asynchronous, there is a lot of value to saying, “I need 20 minutes of focused time to interrogate something that I’ve done. We’re not going to talk. I’m literally going to force us into a room or Zoom. You’re going to read this doc, I’m going to watch you comment on it in real time. I’m going to respond to your comments in real time. And at the end of this thing I’m going to have enough really good input that I can do a huge rub on this thing and get to the next phase.”

Lenny Rachitsky: I love that. So it’s basically instead of, “Hey, I’m sending you this doc to go review, give me feedback,” it’s, “I’m going to schedule a meeting, and the meeting is for you to spend time reviewing this doc and giving me feedback and then maybe we could talk about it.”

Kevin Yien: Yep. And I think a lot of people are going to hate hearing that because like, “Oh my god, I have so many meetings already. Why do I want another meeting that isn’t even a meeting?” But that’s the best kind then, because it’s actual work getting done, right? And maybe you carve out two minutes at the end for one really immediate discussion topic or something. But I don’t think we give enough space in any type of meeting for people to actually think. And when you are just staring at a doc with your camera off and the only expectation is to engage with that thing, thoughts are a little bit better and crisper.

Lenny Rachitsky: And I think with this idea, if someone says, “I want a meeting where you just sit and review this doc,” you could always say, “Let me just review it asynchronously. I’ll give you feedback, I promise. Give me 24 hours.” Right? It’s not like they have to come to this meeting.

Kevin Yien: Although I would urge you to make them come to the meeting.

Lenny Rachitsky: Okay, say more there, because you find that that’s a lot more effective.

Kevin Yien: I think there’s two sneaky things hiding behind that. One is the, “Yeah, I’ll get to this in the next 24 hours.” Maybe they don’t. Maybe you’ve really trust that person and they’re the exception. But beyond that, there is something else to the real time interaction that can happen when you’re commenting and responding on a dock at the same time. I think this is the part that often gets lost, which is the latency between a comments or question and a quick follow-up from the author just pushes that cycle speed really long in a way that doesn’t need to be. And so when people are trying to find how do you move faster, this actually is one of those very good examples of moving slower to move faster.

Lenny Rachitsky: It reminds me Claire Vo, I think it was her phrase of moving one clock speed faster, and just like that’s the way you speed up a company is try to move one clock speed faster, which in this case is just reduce the time between feedback and iteration. I love it.

Okay, I want to shift to talking about a few very tactical things that you’ve found really helpful in your PM career and something you recommend to other product teams. The first is something you call a decision log. You think every PM should keep a decision log. Talk about what that is and why that’s powerful.

Kevin Yien: I will say there’s two different decision logs we could talk about. We’ll focus on the former though. The latter is just as you’re making decisions within your job, you should document those within a PRD. Make sure everyone knows. It’s just a silly, very small thing, but I think every PM should do it.

The other decision log though that I think is quite critical is if we zoom out for a second, every person has something that they can do to slightly increment in their craft. Sprinters have certain exercises that they do. There’s something beautiful about pianists and piano scales where it doesn’t matter if you are just learning the piano or you are a 30-year veteran, you’re still doing your scales, and it’s because it lays the foundation for everything else that you need to do.

And so we all talk about product sense. It’s this super mystical thing that no one knows how to get better at. To me, it’s just a fancy way of saying you can make good decisions with insufficient data, and the core of that is decisions. And so PMs need as many reps as possible in making decisions, documenting the rationale behind those decisions, and then crucially seeing the outcome of them. And so the natural followup would be, “Well, I only have to make X decisions in my job. How the hell do I make more of them?” Look around you. There’s other teams that are making decisions. What would you do if you were in that position with the information you have? Great, write it down. Say why.

There’s other companies that are doing crazy things. What are they doing? What would you do if you were responsible for the roadmap? Write it down. A year later, see what they’ve shipped. You can just do this for anyone. It’s free, and no one takes the time to do it, but that’s how I think you get better at actually making decisions, is just doing more of them.

Lenny Rachitsky: Hearing you describe this, it feels like, “Obviously yes, why aren’t we doing this? How else can we get better if we’re not reflecting back on the decisions we’ve made? And realizing, “Hey, I made a bunch of bad decisions, but I’m always so confident in my decision still, maybe shouldn’t be. So I guess first of all, do you actually do this? How often do you do this? And is there an example of you learning something from your own decision log?

Kevin Yien: Many. And many of them because it was a wrong decision. But yes, I do keep a decision log. I have a separate sort of practice where it’s just a daily log, which is everyone wants the perfect note-taking system. To me, the best note-taking system is inspired by… What is it called? big ass text file, BATF. There’s a funny blog post from 2001 on it, but it’s just, you write everything that happens to you in a day in a bolded list and it’s all in one big note. That way you can command F it, do whatever you want. The way that I keep track of it is I do a little hashtag decision and then write things down just as I think about them. And then I’ll have a reminder to comb back through on some cadence.

And so I’ll first use a positive example, which is a funny one. So if you rewind to, I don’t even know what year, but Shopify had just launched Shop app, their consumer application for what started as tracking your order when you bought something from a Shopify customer and then it’s evolved into a full-blown Amazon competitor, where you can actually find merchants and buy things through it.

When they first launched it though, I was like, “Oh my God, this is so brilliant. They have completely hijacked this specific loop for consumer buying behavior via this very unassuming thing, which is package tracking.” And so that morning I was like, “Whatever, I’m going to quickly draw a diagram of this flywheel that I think Amazon owns today. I’m going to show how Shopify is slowly planting their little seed to take over this and how Shop app fits into it.” I tweeted out. And then I don’t know, that day there must have been 60 Shopify employees that followed me. I was like, “What the hell is this guy talking about?”

And so funny enough, fast-forward, I’ve talked to some of the folks that worked on it and they’re like, “Yeah, nailed it. Here’s what we were thinking. Here’s why.” It’s no longer secret sauce. But that was a really interesting example of both doing a decision log, putting my rationale down on paper. In this case, broadcasting it out, but then having that be a mechanism for it making its way back to me to actually better understand why did they make the decision versus what I thought, because the reasons were a little bit different, but the outcome was the same. So that’s one interesting example.

Lenny Rachitsky: It’s an amazing story. You doing this explains why you’ve been so successful. I could see how this all connects now. I think for a lot of people, they would want to build this habit. Clearly there’s a lot of value here, but they just don’t because they got a lot of other things going on or it’s just like this new thing they have to start doing. Is there anything that helped you adopt this practice of this daily log/decision log that you think might be helpful to folks to motivate them to give this a shot?

Kevin Yien: This is probably just general advice on building any habit, which is start small and just force yourself to do it. And there’s that old saying around, how do you start running as a hobby? You don’t do it by saying, “I’m going to run a mile every day.” You do it by putting your sneakers at the foot of your bed unless you take your shoes off inside, then you put it at the front door, you have your shorts ready to go and you’re like, “I commit to putting on my shorts. And if I decide after getting dressed to go run, that I still don’t want to go run. Okay, fine.” But you build up to that thing.

I think decision logs are the lightest weight thing possible. And so you can start super easy by saying, “You know what? Every Sunday morning I’m going to scroll through Twitter, I’m going to check out Hacker News, whatever it is, I’m going to see something interesting and I’m going to make a bet. I’m going to place my decision on this thing.” Write it down, and then set a calendar invite in X weeks, X months to see what plays out. And that’s all it is, right? 10 minutes once a week, super easy. And then over time you can crank it up. And then eventually you’re just constantly writing these decisions down and then it’s like feeding its way back into you. It becomes second nature.

Lenny Rachitsky: And you’re touching on something that there’s been a little bit of talk on this podcast and newsletter post about this idea of to get better product sense and product taste and also just decision making this case, one of the best strategies is to simulate other people’s decisions and simulate what they’re thinking through and predict what they’re going to do, which is what you’re describing here.

Kevin Yien: Totally. I do want to apply a pretty severe caveat here though, which is, a decision log is not a replacement for building products. It’s a additional complimentary thing that you can be doing on your own. But if you think that you can just sit back in your chair, look out at the market, make a bunch of calls and be like, “Look at how smart I’m getting without actually being hands-on with building a product,” you’re not actually going to get any better. So I just want to interject that

Lenny Rachitsky: Amazing caveat, very important. Don’t just sit and read Hacker News and think you’re going to be become an amazing founder or product leader.

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If someone wants to try this idea of a daily log, what is it exactly? Say decision log or daily log, is it just things that happen today and then hashtag, “Here’s a decision I made, or here’s a decision I think Shopify will make in the future”? Is that the format?

Kevin Yien: Yeah, it depends on how far you want to go down productivity and notetaking as to rabbit holes, but let’s start basic. This is not what I do, but I think it’s the easiest place to start. Spin up a Google doc or a Notion page, just call it daily log and then bullet point out the date of today. And then as you’re going through your day, you have a meeting, just type in the meeting name. If there’s a takeaway, put it under there. If there’s a decision you can make, do hashtag decision. And in this case, say, “Shopify launch Shop app. I think this is their way to take over the fulfillment to buying behavior loop. The reason for that is X, Y, Z.” Follow up on this in six months and then set your calendar invite.

Lenny Rachitsky: Awesome. So as motivation for listeners to try this sort of thing, just look at the success Kevin has had as in his career and how insightful he has been so far and will continue to be. And this is how these happen. This is how your mind learns to see things in a really unique, interesting way. So I know you’re modest and aren’t going to take any credit, but I’m just saying this is how you get better, is trying stuff like this.

Kevin Yien: Footnote, correlation versus causation. It’s all put out there.

Lenny Rachitsky: Could be all genes. Could be completely unrelated to anything you’ve done entire life, I suspect.

Kevin Yien: Could just be me being very lucky, I’ll put that out there.

Lenny Rachitsky: Could also be luck. Okay, so something I wanted to touch on with this decision log idea, and it’s a segue to talking about hiring, is I think interviewing is also really good opportunity to try some like this. I feel like people interview lots of people. They think they know what they’re looking for. They think they’ve made all these decisions. They think they have these amazing interview questions that are going to help them see really good signal, but you never actually go back and see, “Was I right? Should we have hired that person? Did this person work out? Was that question asked them at all inform? Was it at all a leading indicator of anything?” And I feel like this is a really good method for improving your interviewing abilities, is like, “Here’s the questions asked. Here’s what I decided. Here’s what I think,” and then a year later look back, “Was that actually right?”

Kevin Yien: Yeah, totally. I think some of the best companies actually do have a practice around this where they have a 6, 12, 18 month check-in on new hires and they then compare their performance against level hired at and then review against the scorecards. It’s a pretty laborious process. So startups aren’t probably going to do it in the same amount of rigor, but it shows you so much about the holes in your interviewing process. So I definitely plus one of that one.

Lenny Rachitsky: I love that. Oh my god, that puts all this pressure on your score, which is great. So that’s actually a segue talking about hiring. There’s a couple more tactics that I’ve seen you be really good at. So one is just hiring in general. You have a lot of interesting approaches to hiring, including this idea of a unsell email where you try to convince someone not to join your company. Talk about that and why you think that’s effective and then anything else along the lines of hiring you’ve learned.

Kevin Yien: I’ll say the idea of the unsell email came from a place of failure, which is at Square I had shifted into a position where I had to hire a lot of people really quickly. And through that, as a fairly new hiring manager, you’re like, “All right, great. I’ve been told the goal is to hire fast.” Okay, you give me a metric, you’re going to go after it. So you do your best to get as many people in the door as possible. When you’re talking to your recruiting partner, they’re incentivized to increase pass through rates, offer to close rates, all these other things, and so they’re like, “Yeah, this person’s really good.” And you listen. “Yeah, they are pretty good, aren’t they?” Even though there’s a sneaking suspicion that maybe they’re not the right fit, but you move forward anyways.

So fast-forward, there’s a few folks I bring on, and within six months they come to me and they’re like, “This is not at all what I thought I was going to do. This is not the environment I thought I was going to walk into. You didn’t warn me about this, that and the other. I feel terrible. How do I prevent this?” And the reason it’s bad is not just because they feel surprised, but because then, either one, they decide to leave, two, they’re not performing because it’s not the right role or environment for them, or three, maybe the company is still good, but that role isn’t. And so they immediately try to do internal mobility or something to another team, which then leaves you with the same hole. So all of those bad outcomes. [inaudible 00:48:37] “How do I prevent this?” Well, I just got to front load all the gnarly stuff they’re going to find out in their first six months.

And so the practice I started developing is you go through the whole interview process. During that period, you’re collecting all these little concerns, fears, anxieties that they’re not explicitly saying, but they’re definitely hinting at. You got to be pretty honest with yourself about which ones are real. But then when you get to offer stage, I send an email with no more than eight bullet points and I say all the terrible things that are probably going to reinforce their fears. I’m pretty candid about, “This is what it’s like here.” Maybe one example would be, “Hey, I’m a parent and I’m worried about work-life balance.” Maybe they don’t say that explicitly in the interview process, but you get a feeling for it. And I get that as a parent too.

So if I’m at a startup, I’ll be really clear and I’ll say, “You know what? We are a series A startup. We are pushing really hard at product-market fit. The expectation here is going to be that you’re online at 10:00, that you can occasionally hop on a meeting on a Saturday or Sunday.” And if you can tell them that upfront and they can read that whole email and still be equally excited to join, you find yourself an A+ hire. But if they read that and they’re like,” I don’t know anymore,” it’s way better to say, “Great, this is not a good fit. Let’s go our separate ways” than have them leave after six months.

When I first instituted this, I lost 30% of candidates at offer stage.

Lenny Rachitsky: Oh wow.

Kevin Yien: Which drove my recruiting partners insane because they look terrible. Their manager is like, “What the hell are you doing? You’re losing everyone at the very end.” And so they ask, “Can you either not send this thing?” Or, “Can you send it at the very beginning?” And my answer is no, because I don’t know what they’re afraid of yet. I have to go through the whole process to actually understand the thing that’s going to potentially make them say no, and that’s really crucial I think.

Lenny Rachitsky: But once you hear it again, this is such an obviously good idea, clearly not an easy thing to do. In this case where recruiters were upset, is it just get buy-in from folks above, like, “Okay, this sucks for them, but at a macro level, this is good for the business” and they’re like, “All right, let’s keep doing it”?

Kevin Yien: At Square, at least, when I first started doing it, luckily I had a very good relationship with them. So that’s a good starting point. This is maybe going to come across a little bit flippant, but they can’t stop you from sending an email technically. So I’m just going to send the email. And if someone really wants to come and say, “This is bad for business,” whatever it is, I have very strong reasons for why that’s not the case. And now I’ve done it so many times, at least, that I can point to very clear proof points on why this is the right path.

Lenny Rachitsky: In theory, the incentives would be aligned where the recruiter success matters. It’s based on, did they actually have a good time? Did they stay? Did they have good impact?

Kevin Yien: Totally.

Lenny Rachitsky: But since they’re not, obviously incentives aren’t right.

Kevin Yien: I think some companies have shifted on that, where recruiters and salespeople are compensated sometimes in similar ways in terms of quota and whatnot. And so they’ll hold the recruiter accountable to six, 12 post offer tenure before they say, “Oh yeah, you successfully landed this role.” So you can tweak the incentive structure a little bit, but not everyone does that.

Lenny Rachitsky: Okay. So the advice here is to end up with better people that end up being successful and happy. Keep track of the things that will probably be painful for them at the company, and then craft an email that shares upfront, “Here’s what made be a problem if you join, and I just want to be very upfront about it.” I think you actually shared a template of one of these emails in one of your blog posts.

Kevin Yien: Yep, that’s right. I have a fairly real one in [inaudible 00:52:30].

Lenny Rachitsky: Is there anything else hiring-wise? I know there’s probably infinite things that you’ve done, but is there anything else you think might be worth sharing of things you’ve learned to be more successful at hiring awesome people?

Kevin Yien: One final note I’ll make on unsell email is it’s not as if you just send the email and then they either say yes or no. Most of the time they will say, “Thank you. I am cool with six of these. This one freaks me out. Can we talk more?” Definitely. And I think this is where hiring managers have an incredible responsibility that sometimes isn’t taken as seriously as it should, which is, when you are working with someone to get them to join or to offer, you need to bend to do whatever it takes for them. And so if they’re like, “Hey, the only time I can talk is tonight at 11 o’clock after my kids go to bed.”

“No problem. Here’s my phone number, let’s hop on. I will walk you through whatever you want to talk about.” That sort of has to be the place you get to for really strong hires. So that’s just one other thing I’ll say.

The meta point around that is you need to be really invested in the candidates. This probably does change at a certain scale, like if you’re “organization” is hiring a hundred engineers or whatever, you have process around it, you have pipelines, there’s a machine at that point, but I do think the direct hiring managers have a responsibility to be really involved in every individual, because there’s no one who’s directly hiring a hundred people. It’s always within a number that I think you can take on.

Lenny Rachitsky: Okay, so this is the final tactic that I heard you’re amazing at, which is automating user research. On the surface this sounds amazing. “I’m going to automate my user research. It’s going to be amazing. So great.” Talk about why you find this really powerful and important. And then how do you actually do this? How do you automate user research? How have you done this on your teams?

Kevin Yien: Let’s start from why this even matters. I think a lot of folks, going back to what is the point of product management, I think there’s a similar overlap with UXR, like user experience research, and people will say, “Well, if they’re doing research, what do I need to do? I should just be consuming what they’re producing to help with that.”

I know PM should settle for looking through bent glass in my opinion because whether it’s a research report, whether it’s something a salesperson is telling you, whether it’s market research, don’t care, it’s been processed by someone, and PMs need direct exposure to raw material. End of story. And so that’s where I think you just need to constantly be talking to or interacting with whoever is your customer. That’s the foundation.

So okay, if we all agree on that, then the question is, “Well, I don’t have time. It’s so hard. How do I find them? My customer success manager says I can’t talk to the client.” If you are in a situation where the product manager is literally not allowed to talk to a customer, there is something structurally wrong and that needs to be fixed first. So I’m going to ignore that one for now just because that’s a whole other rabbit hole, but you need to fix that in order to even get close to the next thing.

Okay, now the excuse is going to be, “Well, I don’t have time. I don’t want to run a program. I don’t want to have to query and look up and send out emails every week.” There’s so many good resources out there right now, and I think that there are… I’ll speak mainly from a B2B sense. I think B2C, slightly different story, I don’t have as much experience there. But B2B, the two things I will say, one is, there’s this thing called userinterviews.com. Shout out to them. They’re pretty much user testing but explicitly focused on B2B and you can put in super clear criteria on the type of people you want to talk to. They do the heavy lifting and sourcing it, and then you just review and say, “Yes, yes. No, no,” and you can have a steady stream of the exact ICP, you want to go after. ICP is ideal customer profile that you want to go after just coming to you automatically. Amazing.

The next one though, it depends on whether or not you have this tooling in place, but the broader theme behind this next category is your sales team is a research team, and if you don’t view them that way, you are missing out on half the value. And so there’s tools like Gong, which do call recordings, and you can set up filters and alerts for specific terms, phrases, competitors, whatever you want. I don’t care what PM you are in the team. You can find the terms that are associated with what you care about the most. Those then get pushed automatically to a Slack channel or otherwise. And then you can set up workflows either via Zappy or something else to say, “Who was the customer? Pull their email, put that into a sequence, drop in my Calendly” and you just have interviews showing up automatically on your calendar. I will say I cannot take credit for this. Shout out to Beth Hills who was a PM that hired at Mutiny. She is the queen of automating customer research and built an amazing system around this.

Lenny Rachitsky: So the way it works is you set a term for like, I don’t know, POS, point of sale, something in Gong, and if somebody says that or has an issue there, talk about again how that schedules a meeting with you potentially.

Kevin Yien: Yes. So Gong has an integration with Slack. You set up this alert, it posts to Slack the excerpt of the transcript where it was mentioned along with the user or customer name. So in this case, it’ll be Lenny’s Burger shop. lenny@lennysburgershop.com, and then you can set up a Zapier to take every new Slack post from that and then send using, I don’t know, customer.io in email to that person using that field. And then in that template of the email, drop in your Calendly specifically for user research.

Lenny Rachitsky: Wow, that is genius. I love that. There’s another similar tactic that Teresa Torres shared on the podcast in one of the earlier episodes where you have a little popup on your homepage asking people, “Hey, do you want to talk? We’d love to hear feedback on our product. Click here if you want to give us some feedback,” and then that schedules Calendly on the PMs.

Kevin Yien: Totally.

Lenny Rachitsky: PM’s calendar. So you mentioned Gong, customer.io. There’s some tools here. Zapier obviously. Is there anything else you find useful to help automate the sort of stuff?

Kevin Yien: If I take a step back from the automation side or maybe straddle it, depending on the type of business you’re in, there’s ideally people talking about you somewhere, right? It’s either happening on Reddit or Twitter or on some forum or your support forum. There is a community, there’s a destination somewhere. And if there isn’t, then I don’t know, that’s too bad. Maybe you don’t have product-market fit. If you can take advantage of that, you can usually set up something. And if it’s not a Gong or a Zapier, maybe it needs to be just a custom script that you write or you sit down with an engineer to say like, “How do we set up alerting around this thing so that I know when things are happening?”

I think you can’t use the effort required to do that as an excuse to not be talking to your customers more frequently. Because again, if we go back to a product manager should be trying to convert this potential into kinetic energy, part of that understanding and part of knowing the constraints you can apply is just living in that world as much as possible.

The best comparison I can give is, there is a world of difference between reading a report about a lime cook and then standing with a lime cook. You will just pick up on so many ancillary aspects of what their life is like that cannot possibly be communicated in a report. You owe it to yourself as a PM to be exposed to those things all the time.

Lenny Rachitsky: In my experience, every time I talk to a customer, I’m always reminded, “Why have I not been doing this more? How can I not be doing this? It’s absurd that I haven’t done this,” like every time you actually do it. But until you do that, you’re like, “No, no, I know what they want. I’m reading all the customer service talent issues, I’m reading their emails, I get it.” Until you actually talk to them, you’re like, “Oh wow, I had no idea.”

I love that your advice is like, the tactics you’re sharing aren’t, “Here’s how you get a bunch of feedback.” From your users, it’s like, “Here’s how you actually get to talk to the right users.” It’s like in the end of the funnel talking to a potential customer. It’s not just reading a cool… some feedback that they shared.

Kevin Yien: That’s right. I think just like the last point on this one is when you join a new team or start a new role, every PM is budding with energy to do this, “Of course I’m going to talk to my users.” But then you reach a point where you go, “No, I know them inside and out. I don’t need to talk to them anymore. I can write a PRD in my sleep. And I’m so busy doing both, product improvements, maintenance, annual planning, something else.I can use my intuition from the hundred interviews I’ve already done. I don’t need to do one more interview.” And that is a very tempting lie to tell yourself because the world is changing, their lives are changing, and you need to constantly be exposed to those little micro changes in their lives in order to build the product that they’ll eventually need.

Lenny Rachitsky: The best explanation I’ve heard of this is actually from your new boss, Patrick Collison, boss’s boss’s boss, I don’t know how far away you’re from him, where he talks about user research and where it fits in. And the way he described it is, instead of doing user research, talking to customers, informing what to build, it’s talking to user, talking to customers informs your mental of what the customer needs and then that informs what to build.

Kevin Yien: 100%.

Lenny Rachitsky: Beautiful way to think about it.

Okay, so I’m going to take us to a couple recurring themes of this podcast, a couple corners of this room that we have. First of all, I want to go to AI corner, so let’s walk over there. Hello, AI corner. I’m curious if you’ve found any interesting uses of AI in your work or in your life.

Kevin Yien: There’s plenty in work. I don’t know if any of them are interesting or novel. I feel like everyone’s just figuring it out in real time together. So I’ll actually take us in a slightly different direction. And this may be isn’t directly useful to product managers, but I think it’s a really good story.

So when Midjourney V1 was released, if we can remember that far back, it was at least I got beta access on a Saturday. And for what’s worth, I have three daughters, one of them’s seven years old, and so her and I were awake. We were waiting for the other two to wake up and I was like, “Oh, I have this cool new thing. Do you want to play with me?” And she goes, “Of course.” So we log in, we create an account and I type in the first prompt, image gets generated, it’s like a rainbow or something. And then I ask her, “Do you want to try it?” She goes, “Of course.” So she types in unicorn prancing in a field and it generates this hideous looking demented unicorn with two rear ends and a demon flying over it. And I’m appalled at first thinking that she’s going to feel really bad about what she got shown, but instead I look over and she’s in awe. She is amazed.

And then she turns to me and she goes, “Did I draw that?”

“Yeah, I guess you did.” And the thing that I got hung up on was that she used the word draw. She didn’t say, “Oh, I enter a prompt and the LLM produced this thing,” or whatever weird terminology that all of us use. It’s like, “Did I draw that?” I don’t know when it clicked for me, but at some point in time after that I was like, “The concept of these image generation models is the same as a crayon to her. There is no difference in her mind.” And that is an insane change that I can’t even comprehend. And so for me that’s just been I think an experience that I go back to when I think about people asking, “What do you think AI is going to do and what’s the next thing? And is it chat or is it something else?” I cannot comprehend what a child who grew up with a crayon of an LLM is going to think is a good product in 20 years. I need to start crying. But goddammit, I have no freaking clue.

And so I think I have a cheat code actually as a parent, because I get to see how they evolve and use these tools in real time. But all I can say is we are not even beneath the dust on the surface when it comes to what’s going to change.

Lenny Rachitsky: Wow, that is an amazing story, it gave me tingles. It makes me think a little bit about how we used to code in binary and then assembly and now it’s Java, and then I don’t know, all the languages, Python. And now it’s like AI, LLM generating code and it’s the same thing for drawing potentially. It used to be sticks on a cave and then became crayons and pens and iPads and all that stuff. And now it’s again LLMs, so that’s pretty bonkers. Amazing story. Thanks for sharing that. Useful to PMs and non PMs alike.

Okay, I’m going to take you to another recurring corner/segment of the podcast, fail corner. I’m curious if there’s a story of failure that you can share of something that didn’t go the way you wanted and still had a positive impact on your life or career?

Kevin Yien: Well, there’s countless stories of failure, but I’ll choose the one that I think I’ve had to reference the most with people and has been to date the most difficult one to really talk about. I’m on the other end of it, and so now it’s very easy, but it took several years to get there.

So context, I’m [inaudible 01:06:47] my way to PM, I land my first official, by title, PM job at a startup. I made it. I’ve arrived. I’m officially a product manager. And we go up, we go down, all the things happen. Fast-forward, the company is really struggling and so we go through a series of rolling layoffs and I’m round 4 something. At that point in time, my wife was nine months pregnant with our first child, and so I am freaking out. There is the personal side that I’m worried about, but then there’s also my identity that has been completely crushed, because in the moment all I could think was, “I thought I was a product manager. This is evidence I am not,” and I couldn’t get past that.

And so for what it’s worth, this is the one post I have on my website that I actually feel really, really proud of. It’s called Finding Swagger. I can talk about why it’s titled that way, but it’s the thing that I really wrote more for myself because it’s a good reminder to me every time I fall into this mentality again, because that may have been the first time that I really had the feelings of, “I’m not worth it” or, “I’m not meant to be this person,” but it’s recurred several times since then over the past decade. And when I read back through my mentality of how I got to the other end of it, it helps even myself sort of get back on the horse.

So okay, I get laid off, I’m distraught, I have no purpose, I’m nothing. And it was through a lot of reflection, a lot of conversation with friends and my wife where you eventually need to convince yourself that there is a difference between you not being good at something and a business or company not needing that thing at a particular moment in time, or you being very good at something but not in the way that a company needs.

And so I think once I was able to get to that, Square for me was the immediate subsequent role that I took on. And I went into that thing just full steam ahead, I’m going to prove myself. “I know I’m good,” because I think I’m good, “and I am going to prove the hell out of that” mainly to myself, but ideally to other people too.

I think you shouldn’t do things for other people for validation, but the initial success I got to see in launching a product, gaining the trust of my peers, having something that restaurants were texting me about, saying, “I can start my restaurant because of this. I didn’t go down during rush hour because of this,” that gave me the validation to say, “Okay, I am competent at this thing called product management.” And then from there you can continue to build and continue to grow.

But I think right now, the market’s weird, right? The market’s wonky. There’s a lot of really good talent that is just getting hit over sideways. I have a lot of friends that are having the same mental conversations around, “Well, I guess I’m just not worth it. I guess I wasn’t cut out actually to do this job, do this role, be of this purpose.” In some cases, maybe that’s true and you can sort of have a career transition or a pivot in your life, but I think it’s worthwhile to reflect on what are the things that were in your control that you can now change moving forward? And then what are the things that were truly out of your control that you can now apply to find a better fit? And that’s one of the big things that I’ve been able to, I think, come around to.

And it’s really hard because early on I think it’s very tempting to associate a lot of different things with your identity. You’re like, “I’m a startup guy. I’m a PM, I’m a fast whatever, I’m a fast thinker.” And when an event happens that pokes at that part of your identity, the rest of it crumbles. And so long story short, I think it’s really important for folks to use these moments where it feels bad and feels like a failure to reevaluate what parts are actually part of your identity and which parts are in your control to change in whatever you do next.

Lenny Rachitsky: Wow, what an important and great story. As you mentioned, a lot of people are dealing with finding it hard to find a new gig and a bunch of layoffs. I think this is going to help a lot of people. The two categories you shared I think are especially powerful. So the advice here is just separate, “This company just doesn’t need someone with my skills right now” from, “I’m not good at these skills.” Can you just share those two kind of things that might be true that you may not be recognizing about why they maybe laid you off again?

Kevin Yien: Totally. So one is the business just doesn’t have a need for you. They got ahead of their skis and that’s their fault. They probably admit that, but that’s not up to you. The second one though is my skills and the way that company operates are not compatible. This one I think is really, really important because I’ve seen so many times where there’s been a PM engineer, designer, whatever role, they cannot make it work at company A, and then you see them five years later just killing it in company B and you’re like, “Did they change as a person? Did they get super good at what they were bad at before?” Maybe a little bit, but honestly it was just a change in environment. And when you find the right environment in the right role, you just flourish.

And I think this is actually… Sorry, we’ll go back to hiring for just a moment or at least management.

Lenny Rachitsky: Please.

Kevin Yien: This is why performance conversations can always feel so difficult because it seems like you’re telling someone you are bad, and as the recipient you’re like, “I am bad.” No one wants to hear that. But the reality is, you are not bad. It is that maybe the way that your environment is working, the machine that you exist as a part of, is not the kind that you thrive in. And so it’s within your control to decide, “I’m going to change how I work to fit that environment” or, “I’m going to find a different environment that actually fits the way I work much better.” And that’s empowering.

Lenny Rachitsky: I think that also applies a lot to interviewing. A lot of times you interview, don’t get the job, and you exactly feel like, “Oh, I’m just not good enough.” But really that company’s way of working just may not gel with the way you operate. Like Uber operates very differently from Airbnb, operates very differently from Google. And so it’s not that necessarily something you’re doing wrong, they just don’t think you’re fit.

And this connects to something. I just had another guest on the podcast. He was a brain science dude, and he talks about how every company has this kind of habitat. What habitat are you creating for your employees to enable them to think differently or to be shut down and not feel like they can be creative or try big things or not? And basically, the way he just kind of to leverage that metaphor, like you may be a palm tree and you’re trying to join Antarctica and it’s not going to go well.

Kevin Yien: Totally.

Lenny Rachitsky: You got to find Palm Springs or some hard place. Kevin, this has been amazing. Okay, so before we get to very exciting lightning round, is there anything else that you think is important or valuable to share, leave listeners with? And if not, absolutely.

Kevin Yien: I think we’ll probably find ourselves on interesting detours to the lightning round, so let’s roll in.

Lenny Rachitsky: Kevin, with that, we’ve reached our very exciting lightning round. Are you ready?

Kevin Yien: Hell, yeah. Let’s do it.

Lenny Rachitsky: Let’s do it. Question one, what are two or three books that you’ve recommended most to other people?

Kevin Yien: I’ll start by saying the type of book by volume that I read and get the most joy from are autobiographies and memoirs. It is just the ultimate cheat code to spend time with people that you respect, are interested by, or want to learn from.

Could you imagine what it would take in real life to sit down with Albert Einstein for 50 hours and just have him talk to you about his life? Impossible. But you can read and pretty much get the same thing.

So anyways, strong requirement or a strong suggestion, go read autobiographies and memoirs of people that you respect, mostly for their mental model and way to approach thinking, less about specific things. But the one book that I read without fail every year has a very misleading title. It’s called The Courage to Be Disliked. I think it’s been mentioned previously on the podcast, but it covers… It’s a very Socratic method style, so it’s about a philosopher and a young person, and it tries to teach you the ways of Adlerian psychology, which is sort of counter to Jungian theory.

The reason I really like it is because it makes me uncomfortable. So the whole premise, in my opinion, behind the book and other in psychology is focus on what you control. That’s the one line. Don’t worry about everything else. Don’t worry about what other people think. Don’t worry about what other people do. You cannot control those. You focus on yourself and you focus on the actions you can take. And be the person that you think will attract other people, that you want to be around.

There’s some really pointed notes in there that I’m like, “Ha-ha-ha-ha. I don’t fully agree with that one,” but it always pushes me to question something about what I believe. And so in every physical copy of a book I have, I write the date that I started reading it again. The front inside cover of this book, I think it’s been seven or eight years at this point that I’ve read it every single year.

Lenny Rachitsky: Wow. It’s like a decision logging in another context almost.

Kevin Yien: Yeah, a little bit. I would say the other book I was going to mention is The Paper Menagerie. This actually shout out to Sean Rose for… I’ve never met him, but I really appreciate Sean. He was one of the early, if not, first PMs of Slack, and he used to be really loud on Twitter in a very good way, and I think I learned a ton from stuff that he would post. But one of the things that he posted was this book. It is just the most beautiful collection of essays that span sci-fi and fantasy. And so if you’re into that kind of stuff, if you like exhalation, then Paper Menagerie is even better.

Lenny Rachitsky: Oh, shit. Guess I got to add this book to my list. I do love exhalation.

Kevin Yien: There you go.

Lenny Rachitsky: Oh, man, this job is tough. I get to learn all these amazing books and then I got to read them, but I don’t have time. Hard.

Speaking of more time, next question. Do you have any favorite recent movies or TV shows that you really enjoyed?

Kevin Yien: There’s less time for either these days. I will say not novel, the Bear holds a very special place in my heart right now, both because I worked in restaurants and I got to build for them. And so seeing the details that they do actually gives me a lot of anxiety, but I really appreciate the craft they put into it.

The other show, actually, I think this is the first time, Physical 100. So this is a Netflix show. It’s a Korean show about a hundred different bodybuilders, athletes, what have you, on who has the optimum physique or whatever. I don’t really care about that part. The two things I love about the show are, one, it’s ridiculous what people are capable of. You see what they can physically do and you’re like, “Oh my God, that’s amazing what they can put their minds to.” The other part though, and this is maybe a trend of Korean shows that I’ve noticed, is the amount of respect they have in this competition is bar none. You have this guy who is historically famous, was the top champion in judo or something, and you have all these other athletes that are 15, 20 years younger, and they’re bowing and just humble to compete against the guy. I kind of wish that more American Joes had that level of respect as opposed to just trying to find the most conflict. There’s something that I really like about that.

Lenny Rachitsky: That’s beautiful. I’ve started that show, but I haven’t continued it, so I’m going to revisit it.

Kevin Yien: Cool.

Lenny Rachitsky: Do you have a favorite product that you’ve recently discovered that you really like?

Kevin Yien: We got a really old 2002 Jeep to work on with my daughters, just like a true junker. And as a result of that, we’re repairing it. We’re taking off the rust, replacing parts, and so there’s these little magnetic trays that you can hold screws and nails and whatnot, so they don’t go flying and rolling around everywhere. It’s stupidly useful when you’re working on a car. And the girls love it because they can use it for other things like collecting hair clips or whatever else. So magnetic trays, shout out.

And then selfishly, I will say my buddy Arjun Mahanti has an app called Circuit. If you search the app store for Circuit, like C-I-R-C-U-I-T, HIIT timer, it’s such a delightful little app that lets you track Tabata sex or whatever else to just get a little workout in.

Lenny Rachitsky: Super cool. Magnetic tray is not boring at all. That is extremely cool and it has a really cool story too. Do you have a favorite life motto that you often come back to and find useful to share with friends and family in work or in life?

Kevin Yien: I think we’ve actually maybe touched on both of these. I’ll cheat and I’ll pull one from maybe each parent so that in case they see this, they don’t feel like I’m favoring one of them.

So my mom’s side, I think something that she would always repeat to me growing up is everything happens for a reason. I hated that growing up because she only said it when something bad would happen. Something bad happens, she goes, “Everything happens for a reason,” and I’m like, “No, it doesn’t. Life just sucks.” And to no surprise at this point in the conversation, I’ve now grown to really, really appreciate that piece of advice because what it’s actually trying to communicate is, when something happens, good or bad, frankly, don’t dwell on it. That’s the past. Focus on what you want to do and then just move towards that. And then in most cases, you’ll be able to look back in one, five, 10 years and connect the dots in a way where the story makes sense in your mind. And so just having that shift in perspective I think has helped me a lot to not overreact to anything that happens in my life. So that’s one side.

And then on my dad’s side, so the funny origins of this, unsurprising to anyone with Asian parents, I’m a spunky little 7-year-old, I come home with my math test one day. I got 97%. I think that’s pretty good. I go show it to my dad with beaming eyes and pride. He sort of stares down his nose at it, looks at me, “Where’s my other 3%?”

Lenny Rachitsky: Oh, my God.

Kevin Yien: I’m just distraught and I sulk away. I’m very sad. I study hard. I do the next math test, I get 100% yes. All right, dad’s approval, here we come. I come flying back, I put the test in his hands, he stares down his nose at it, looks at me, “Where’s my other 3%?” I’m so confused. I’m like, “I got 100 out of 100. I have no clue what you’re talking about.” He just looks me down the eye and goes, “Who said a hundred is the most you can get?” At that age, I literally had no clue what he was talking about. And he had to reframe it for me in the moment around like, “Well, was there extra credit? Can you just write your own problems to challenge yourself more? Could you have given yourself another test? And maybe the teacher won’t give you credit, but you give yourself credit for doing additional work.”

I think I carry that theme forward where there’s this weird transition we all go through from childhood to adulthood where we no longer receive homework, we’re responsible for defining the work that we do. And when you do that, if all you do is the minimum of what defined the 100% of what your job requires, you’ll never grow. And so it’s up to you to actually find what is the additional 3%? There’s always three more percent. So that’s my dad’s lesson.

Lenny Rachitsky: Kevin, you’re blowing my mind. There’s so many great stories, you’re just full of them. And I feel like this lesson also applies really well to product and building product and founding companies.

Kevin Yien: Totally.

Lenny Rachitsky: Just pushing further than people expect and making it a lot more delightful than the minimum bar.

Final question, speaking of things that maybe people don’t expect and may not understand is possible, looking at you, nobody would’ve guessed that you’re a competitive eater at some point in your life. As a final question, tell us about this part of your life. What did you eat? How does this work? How far did you get in this path?

Kevin Yien: It’s probably misleading to say that I was a true competitive eater. I wasn’t on the circuit with a… I forget his name, but Johnny Chestnut.

Lenny Rachitsky: [inaudible 01:24:21]. Oh yeah, Chestnut

Kevin Yien: Back in the day, that’s like the OG competitive eater on the hotdog circuit, I guess.

Lenny Rachitsky: Right.

Kevin Yien: For me it was more eating challenges. And so whenever I would travel, I would find the local eating challenge, whether it was time-based, volume-based, something else, and just try to see what I could push my body to do. I was blessed with a great metabolism, so I never really had to worry too much about anything else. And the origin, the first moment of this was when I was 14, my sister was going to college in Minnesota and there’s this steakhouse up there called Manny’s, which is where the Vikings Frontline goes to after every game. And they have this ridiculous 97 ounce order house. I don’t know how many pounds that is, but it’s too much meat for a human to consume.

Lenny Rachitsky: 97 ounce.

Kevin Yien: 97 ounces, yeah. And so I sit down, I order it thinking, “This is going to be great.” They put it in front of me, it’s a monster. You have to eat in under an hour. And so 45 minutes into it, I’m halfway through and about to die. And the catch is, if you finish it in under an hour, you get it for free. And so my dad again leans in and goes, “You can’t afford not to finish this.”

And so, “Message received, sir.” Hunker down. I plowed the other half in 15 minutes. I then slept for I think three days afterwards. But after that I was like, “Oh my God, if I could do that, what else could I do?” And so, [inaudible 01:25:54] carried for, I don’t know, nearly a decade of trying to do these interesting challenges.

Lenny Rachitsky: Wow. I don’t know how that’s physically possible, but clearly you did it.

Kevin, this has been wonderful. I think there’s so many lessons here for people in so many ways, life and work and parenting. Two final questions, where can folks find you online if they want to follow you and learn more from you over time? And how can listeners be useful to you?

Kevin Yien: I’m on Twitter, just @kevinyien. Technically, I’m on LinkedIn. I don’t post over there. I probably should. I hear it’s very good. But that’s where you can find me. Also, my website. I don’t write that often, and I don’t have an RSS feed, which has always been on my backlog, and I’m always too lazy to do. But one day I will add it.

One quick note, I’ll actually make on websites. So on one hand, I love all the different website builders that exist. It’s amazing what we’ve enabled anyone to be able to do. There is something really special about having your corner of the internet that you built sort of hand by hand, line by line. And so my website is, it’s a GitHub page. It’s hosts on GitHub pages, but it’s just raw HTML, CSS, nothing fancy. I get so much joy every year just doing a slight tweak or cleaning of it. And so I really do recommend that for anyone with the curiosity and the desire to buy your domain, even if you’re never going to write anything on it, you’re never going to share it out, just own a little piece of the internet. It feels good.

Lenny Rachitsky: I love that. I didn’t know that about your website. And I could see it now as I go there. It’s .html, which you don’t see as much anymore.

Kevin Yien: Exactly. [inaudible 01:27:37].

Lenny Rachitsky: And then… Yeah, can listeners be useful to you.

Kevin Yien: This is going to sound trite, and it has nothing to do with product necessarily, just be kind. Make for a nicer world, right? Say thank you a little bit more often. Hold the door open a little more often. Wave if you cut someone off in a car. I think there is a temptation and incentive structure to create conflict intention. And in most cases, the world would just benefit from a little bit more kindness.

Lenny Rachitsky: What an incredibly beautiful way its ended. Kevin, this was so much fun. I’m so glad we did this. Thank you so much for coming on.

Kevin Yien: Thank you for having me.

Lenny Rachitsky: Bye, everyone.

Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

Glossary

English	中文
Adlerian psychology	阿德勒心理学
Albert Einstein	爱因斯坦
Anthony Bourdain	Anthony Bourdain（美国名厨、作家、电视主持人）
Arjun Mahanti	Arjun Mahanti（Kevin Yien 的朋友，Circuit App 开发者）
beta access	beta 权限
Beth Hills	Beth Hills（人物名，Mutiny 的 PM）
big ass text file (BATF)	big ass text file（BATF，一种笔记方法：把所有内容记在一个大文本文件中）
Bruce Bell	Bruce Bell（Kevin Yien 在 Square 时的经理）
cadence	节奏
Charlie	Charlie（Mutiny 的 CEO）
Chestnut	Chestnut（指 Joey Chestnut，美国著名竞食选手，Kevin 口中误称 Johnny Chestnut）
Chris Dixon	Chris Dixon
Claire Vo	Claire Vo（人物名）
clarity at scale	规模化地传递清晰度
decision log	决策日志
Exhalation	《呼吸》（书籍名，Ted Chiang 短篇小说集）
Finding Swagger	《Finding Swagger》（Kevin Yien 的个人博客文章）
flywheel	飞轮
GA（General Availability）	GA（产品正式发布）
Gong	Gong（销售通话录音与分析平台）
Hacker News	Hacker News
HIIT	HIIT（高强度间歇训练，High-Intensity Interval Training）
ICP (Ideal Customer Profile)	ICP（理想客户画像，Ideal Customer Profile）
Jeff Weinstein	Jeff Weinstein（Kevin Yien 的同事）
Joan Didion	Joan Didion（美国作家）
jobs to be done	待办任务（Jobs to Be Done）
Jungian theory	荣格理论
Kevin Yien	Kevin Yien（嘉宾）
Lenny Rachitsky	Lenny Rachitsky（主持人）
lime cook	石灰窑工人（此处 Kevin 可能误用或指代特定工种，译为石灰窑工人）
LLM	LLM（大语言模型）
LNO framework	LNO 框架
Manny’s	Manny’s（明尼苏达的一家牛排馆）
menu group	菜单分组
Mutiny	Mutiny（公司名）
Patrick Collison	Patrick Collison（Stripe CEO）
Paul Graham	Paul Graham（美国程序员、风险投资人、作家）
Physical 100	《Physical 100》（Netflix 韩国竞技真人秀）
PM (Product Manager)	产品经理
PRD	PRD（Product Requirements Document，产品需求文档）
product sense	产品直觉
product-market fit	产品市场匹配度（product-market fit）
prompt	prompt（提示词，AI 图像/文本生成中的输入指令）
rolling layoffs	滚动裁员
Sean Rose	Sean Rose（人物名，Slack 早期 PM）
Shop App	Shop App（Shopify 的消费者应用）
silent read	沉默阅读
Square	Square（公司名，Kevin Yien 曾工作的地方）
Square-ism	Square 式做法
Tabata	Tabata（一种高强度间歇训练模式）
Teresa Torres	Teresa Torres（人物名，产品发现领域专家）
The Bear	《熊家餐馆》（美剧）
The Courage to Be Disliked	《被讨厌的勇气》（书籍名）
The Paper Menagerie	《纸异兽》（书籍名，刘宇昆短篇小说集）
tuning fork	音叉
unsell email	反向推销邮件

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