The Exchanges

Q I do want to start, you mentioned your transition from engineering to product management there, and really finding your home there. You know, the word product management and the term is so thrown around today. I just want to clarify, what exactly is product management, Lenny? Let's start there.

A Every PM you ask is going to have their own, like, definition. It's such a vague, unusual, ill-defined role, and it's one of the more common interview questions for PMs is like, What is product management? And it's because it's so unclear, but there's a few ways I think about it. The simplest way is you could kind of break it down into these three jobs of a product manager. Basically, your job as a PM is to shape the product, to ship the product, and to synchronize the people, and all of that in order to drive impact for the business. Just kind of breaking that down. Shaping the product means taking insights from customers and data and stakeholders, figuring out what to build, what to prioritize, and how to have the most impact on the business. Basically, figuring out what to be building. Shipping the product is basically... Shipping high quality product on time, and free of surprises, it's kind of like the project management layer of product management, and then synchronizing the people is essentially aligning everyone. Priorities, timelines, roadmaps, vision, strategy, and making sure time isn't wasted, making sure everyone's moving down the same path.

AI assessment note: “your job as a PM is to shape the product, to ship the product”

Q I do want to ask you, we've covered kind of the nomenclature. We've covered the hiring process. In terms of the actual workings, I want to touch on a couple of really Core points. You know, product reviews are so central to really any product team, and especially product managers. How do you think through how to do product reviews?

A So broadly, maybe thinking about just problems that often arise in these reviews where a team has come to a leader and they're just like, hey, here's our latest update on designs that we're working on. I think the most common problem in these meetings that causes all kinds of wasted time is not connecting back to the problem that you're solving as a team, whether it The problem that feature is trying to solve. A lot of times you come to a product review, you're like, oh, check out these great new designs. Here's how it's going to work. Here's the flow. Here's the interactions. People start getting sucked into. It's like, awesome. Look at these colors. Oh, maybe we should move spacing here a little bit. Maybe we should move the button up here, but you lose sight of just like, is this actually achieving what we're trying to achieve as a team and as a business? Like, is this going to increase conversion of a specific type of user through this flow? Is this going to reduce contact rate? If that's what we're trying to do, is this going to increase adoption of a new feature? So you always want to come back to, here's the problem we're trying to solve with this feature. The way to do that is at the beginning of the review, you want as a team to start with, here's the problem we're solving. Just like put it up on, you know, the slide. And then if you're the leader, you want to ask, you…

AI assessment note: “at the beginning of the review, you want as a team to start with”

Q Speaking of kind of a mistake or a decision, I do want to touch on a personal experience. Again, I always find a lot is learned from mistakes that one makes. If you take me back to a product decision you made that was a mistake, what was it? And what did you learn, Lenny?

A The biggest product mistake that I made. So the first Product that I worked on at Airbnb. So they acquired our company, and what they wanted us to build was a way for travelers and Airbnb to find things to do when they're traveling in a city. The founders kind of, like, oriented us towards a direction, almost a solution, and the solution they wanted us to build ended up being, how do we help travelers connect with other travelers in a city? If Harry's in London and Jane's in London, hey, they should, like, there's all these Airbnb guests in London right now. What if they hang out together and do awesome stuff? What we ended up building is a way for, like, You to propose. Hey, I'm going to go to Big Ben. I want to go to Big Ben. Who wants to come with me? And it was all very grassroots driven. There wasn't like a local expert of any kind. It was just you suggesting to do this thing. And so we built this thing, launched it. Nobody really wanted to do this. It's like a big risk to take when you're traveling for a short amount of time to go on this random experience with random people. No one knows what they're doing. It's just like a bunch of travelers and Airbnb trying to figure things out. So we launched it and just, it didn't go very far. And that was the first thing that we worked on at Airbnb. And they basically got Killed. And it's like a classic product management lesson is…

AI assessment note: “spend time doing a little bit of research and dig into, is this really a problem”

Q your career was clearly mistaken. I thoroughly agree with this And I'm glad that we share that perspective. I am intrigued though. Seven years at Airbnb is a long time at such a incredible, but also iconic institution of our time. In terms of like your lessons and the impact from it, how do you think your time and your seven years at Airbnb impacted your approach to product today?

A Airbnb is a really special place. It's not an accident it has done as well as it has done. I think it's like a hundred billion dollar company now, and it's not a surprise to be honest. A few things that stand out that have stuck with me, About what I've learned at Airbnb. One is just this idea of never settling for good enough and always setting the bar incredibly high. I always have this memory of this moment where a team that was kind of sitting next to me, it wasn't my team, but they were about to launch this product called Neighborhoods, and they're trying to update the homepage to launch this product. One of the co-founders, Joe, walked by, and she asked him, hey, what do you think we should do with this homepage to announce this new product? And he's like, build something the internet has never seen before. And I was like, all right, great. And she's like, hey, we got a week. Let's do this. She did build something very cool. She built kind of this, like, parallax-y neighborhood photo thing, and it was really cool, but it's just kind of a sign of just the way Airbnb founders and the people they hire think is just how do we go beyond the bare minimum, and how do we do something really unique and different? Brian's kind of famous for in meetings always being like, how do we 10 X this goal? How do we 10 X what we're trying to do here? How do we go a lot bigger? And so that ha…

AI assessment note: “One is just this idea of never settling for good enough and always setting the bar”

Q speaking of scaling our product org, me as the founder, I'm entering the hiring process now, and lucky me, you're helping me. So when we think through this, I've never done this before. How do I structure my hiring process for the product team, Lenny? I actually just like break it down for me, like meeting by meeting, because I have no idea what to ask and what to expect.

A Yeah, totally. There's a lot of ways to do this. I think one thing with interviewing that's interesting is rarely do people actually know if their interview process is like Good. Because, like, how much data do people actually have on, is this going well? Are we interviewing? Are these questions good? What is it really telling us? Like, very few companies have a lot of data to really understand what's going on, so there's a lot of ways to do it. Unclear exactly what the best way to do it, but the way I like to approach it, and it works, seems to work, is you basically bring a candidate in for a whole day, try to break up the interview process to a project at the beginning of the day, and then a bunch of one-on-one interviews. The second half of the day, and before I get into those two, just like broadly, the things you want to be looking for in a PM, there's kind of these five key skills. Focus on their execution skills, their collaboration skills, their just broad leadership skills, their vision plus strategy, and then their ability to do customer user research and extract customer insights. Five things to focus on. Okay, so they come in. The first thing I like to do is do a little project, and the way I like to approach it is I sit them down and I give them a Prompt. Print it out. Here's like a problem that you as a PMR needs to solve. It could be like, how do we increase ado…

AI assessment note: “bring a candidate in for a whole day, try to break up the interview process”

Q Well, you are far too kind, but I want to start with a little bit on you. So talk to me. How did you make your way into the world of product, come to be at some incredible places like Airbnb very recently? What was that entry for you?

A Sure. So I was born in what is now Ukraine. Back then I was the USSR, and I'm Jewish, my family's Jewish, and we, my parents always kind of wanted to get out of there, to get out of Russia. And so we immigrated to LA. There's actually this whole, like, movement of Jewish people out of Russia in 88. Took, like, a Jewish federation to help us get out of there, and there's, like, protests in Berkeley and on college campuses to, like, help Jews leave Russia, and so we got out of there. Moved to LA. Got a job right at college in San Diego at a startup. I was their first engineer. Moved up the ranks. Ended up leading engineering at this company. Ended up doing some R&D stuff. They got acquired. Then decided, hey, I want to start a company. I had this goal I set for myself. I'm going to start a company in two years. Two years later, exactly that. I actually ended up moving to Montreal to start this company for a number of reasons. I built the prototype, launched it at South by Southwest of all places. It actually did really well. We got a lot of attention. Raised some money, moved to San Francisco actually at that point, because our investors are like, you got to be an SF. You're starting a company, even though we were in Canada. A year later, the head of product at Airbnb reached out to me, and he's just like, hey, we should work together on some stuff. Maybe there's like a way you c…

AI assessment note: “A year later, the head of product at Airbnb reached out to me”

Q Speaking of kind of a mistake or a decision, I do want to touch on a personal experience. Again, I always find a lot is learned from mistakes that one makes. If you take me back to a product decision you made that was a mistake, what was it? And what did you learn, Lenny?

A The biggest product mistake that I made. So the first Product that I worked on at Airbnb. So they acquired our company, and what they wanted us to build was a way for travelers and Airbnb to find things to do when they're traveling in a city. The founders kind of, like, oriented us towards a direction, almost a solution, and the solution they wanted us to build ended up being, how do we help travelers connect with other travelers in a city? If Harry's in London and Jane's in London, hey, they should, like, there's all these Airbnb guests in London right now. What if they hang out together and do awesome stuff? What we ended up building is a way for, like, You to propose. Hey, I'm going to go to Big Ben. I want to go to Big Ben. Who wants to come with me? And it was all very grassroots driven. There wasn't like a local expert of any kind. It was just you suggesting to do this thing. And so we built this thing, launched it. Nobody really wanted to do this. It's like a big risk to take when you're traveling for a short amount of time to go on this random experience with random people. No one knows what they're doing. It's just like a bunch of travelers and Airbnb trying to figure things out. So we launched it and just, it didn't go very far. And that was the first thing that we worked on at Airbnb. And they basically got Killed. And it's like a classic product management lesson is…

AI assessment note: “The biggest product mistake that I made. So the first Product that I worked on”

Q One thing that will determine the feedback that you get and the direction of the meeting is who's in the room itself or in the Zoom call itself more appropriately these days. How do you think about who should be in those reviews?

A Generally, the real thumb is it should be as small as possible. The more people in a meeting, the more time everyone's spending, the more just things start to come up. But broadly, who's involved in the project, I think is a simple way to think about it. If it's like 10 engineers, you don't want to bring all 10 engineers. You could just bring a representative of engineering or the engineering manager. I think things maybe have changed with Zoom and remote work, and maybe it's a lot easier for a lot of people to come and just kind of stay on mute and listen. The rule of thumb is you want to make it as small as humanly possible while making sure people that need to hear that feedback are in the room.

AI assessment note: “rule of thumb is you want to make it as small as humanly possible”

Q Well, you are far too kind, but I want to start with a little bit on you. So talk to me. How did you make your way into the world of product, come to be at some incredible places like Airbnb very recently? What was that entry for you?

A Sure. So I was born in what is now Ukraine. Back then I was the USSR, and I'm Jewish, my family's Jewish, and we, my parents always kind of wanted to get out of there, to get out of Russia. And so we immigrated to LA. There's actually this whole, like, movement of Jewish people out of Russia in 88. Took, like, a Jewish federation to help us get out of there, and there's, like, protests in Berkeley and on college campuses to, like, help Jews leave Russia, and so we got out of there. Moved to LA. Got a job right at college in San Diego at a startup. I was their first engineer. Moved up the ranks. Ended up leading engineering at this company. Ended up doing some R&D stuff. They got acquired. Then decided, hey, I want to start a company. I had this goal I set for myself. I'm going to start a company in two years. Two years later, exactly that. I actually ended up moving to Montreal to start this company for a number of reasons. I built the prototype, launched it at South by Southwest of all places. It actually did really well. We got a lot of attention. Raised some money, moved to San Francisco actually at that point, because our investors are like, you got to be an SF. You're starting a company, even though we were in Canada. A year later, the head of product at Airbnb reached out to me, and he's just like, hey, we should work together on some stuff. Maybe there's like a way you c…

AI assessment note: “head of product at Airbnb reached out to me, and he's just like, hey”

Q What are the questions which are most revealing of customer data that you do want to ingest versus don't want to ingest? Bad example, what do you want us to build? What's the right way to ask the question?

A So if you think about these three kind of Time horizons of how you use product. There's things you've done in the past. There are things you're maybe doing now and things you might do in the future. A classic rule of research and talking to customers is you never want to focus on what people might do because we're really bad at predicting what we will do. We think we're going to go to the gym. We don't. We think we're going to not buy a gadget. We end up going and buying it. We're just like really bad at predicting our behavior. And so what you want to focus on is what have you done in the past? What problems have you had that we can maybe solve for you? What are the issues you've had with this product that maybe we can fix? So it's a lot of watching people use a product and then asking about things they've done in the past. There's a really great book about this topic that if folks want to dive deeper called the mom test, all about how to properly do user research. And it's called the mom test because your mom will always be really nice to you. She's not going to tell you like the truth about what's wrong with your product. And so your job is to get past that and get real insights about what's really broken. And there's like a whole list of questions in that book, actually.

AI assessment note: “never want to focus on what people might do... focus on what have you done”

Q Can I jump in there? Who do you invite into the project to witness this and be part of it? And then like, how do we ensure that we really stress test their thinking in those questions?

A So it depends on the size of company you have, but basically you want to invite the people that will be working with them in the future as much as possible. So an engineer, Engineering manager, then the designer, maybe another PM, the hiring manager, user researcher, if you have someone like that. So it could be like, you know, three, four or five people in terms of stress testing them. You just, if you do this enough, you start to have a set of questions that you know are going to be interesting. And so you start to kind of build a habit of like, all right, this is going to be a thing that'll make them think a little bit deeper. Personally, I hate putting people on the spot with a really hard task because as a PM, you don't need to be like on the spot solving really hard problems. You have time to think. And process and research. That's why I like to give them time to think about this thing, not just like, cool, design the solution on the whiteboard now and go.

AI assessment note: “you want to invite the people that will be working with them in the future”

Q got this project. This has taken maybe three hours, maybe, say, 90 minutes for the start, and then 90 minutes for the presentation and the questions, and now we've got the one-on-one interviews. In terms of the one-on-one interviews, Interviews. Again, how do you structure them? What are you looking to get out of them? If we're planning the rest of the day, how do you want this to go?

A So there's these kind of five skill sets roughly. And then often there's also just like cultural questions, just like, are they a fit here? Do we want to work with them? And so what you usually do is just split up questions across each of those skills across team members. And people have, they're like, you're responsible for understanding if they're a great executor. Ideally as a company, you kind of have this rubric of here's questions that we will ask to help understand if they're great at executing. Execution. And here's answers we're looking for. You kind of split them up across, and it's just like one-on-one in an interview. You ask them questions, they answer, you write notes, and then at the end of the day, people submit, here's just like how we feel about this candidate. Should we hire them or not? I could share some questions that I like.

AI assessment note: “split up questions across each of those skills across team members”

Q I love that as a startup CEO for an ancillary business. We're going to dig into the different profiles and how to uncover them, how to hire. I do just want to ask one that actually I don't even know today, which is really fucking embarrassing. Head of product versus chief product officer. What's the difference? Any advice for me, the founder, on when to hire?

A Titles are very inconsistent when you hire your first PM. You often call them a head of products. It doesn't really mean that much to be head of product. Chief product officer is usually, like, a very senior person that has done product for a long time. Basically, I think the question is then, when should you hire, like, a really senior PM to come take over? From what I've seen, it makes sense to do that maybe when you're, like, series C or something, when you have maybe a dozen PMs. CPOs are really good at org design, hiring senior people, building new business units and lines, and so I think when you're ready just to, like, scale your product org and start hiring like crazy within product, I think that's A time you want to probably bring in someone super senior, CPO type.

AI assessment note: “makes sense to do that maybe when you're, like, series C”

Q I had Scott Belsky on the show the other day, and one of his biggest strengths, a lot of his references said, was his ability to work cross-functionally between product and design. When you think about how you work with Product and design teams, and specifically from a PM background working with design, how do you think about working most effectively with designers and design teams?

A Having a great designer is like having a superpower on your team, in my experience, because everything just gets better. Decks look nicer. Your product obviously looks better. Engineers start to feel better about their product because it's looking so much better and feels so much better. If we're focusing on design, if you have an awesome designer on your team, you should feel really lucky. In terms of how to work with your designer, basically you want to treat them like a And not like someone that's working for you as a product manager. Kind of zooming out a little bit, if you think about a product team, there's this core leadership triad that makes up the leadership group of a product team. The PM, the engineering manager, and the designer. Essentially the leads of a product team. So similar to how you work with your engineering manager, your designers basically appear to you. You have maybe like a percentage more say over where things go just because it's useful for somebody to have a little more influence, but otherwise basically they're your peers. And then very, I guess, concretely, how do you divide up work with a designer and a PM? Definitely this Venn diagram overlap of skill sets and interest, but a simple way to think about it is the PM's job, eighty-twenty. 80% of their job is to identify the problem that needs to be solved and make clear, here's what we're trying t…

AI assessment note: “PM's job, eighty-twenty. 80% of their job is to identify the problem”

Q Can I ask, what's your writing process like? You know, you write incredible pieces. What is the process like?

A Since it's an advice column, people send me questions. I have this endless list of questions from readers. I pick a topic I'm excited to write about because I find that if I write about things I'm not excited about and things that just people want me to write about, it doesn't end up right. So I pick a thing I'm really excited about at the time. I have kind of three different kinds of posts. I have a post that's an answer, like I give the answer myself. Guest posts where I find an expert does an in-depth answer. And then I have research posts where I go figure it out because I don't have the answer. So if it's the third kind, I just start pinging a bunch of people, ask them questions, start gathering information, Stick it in a big doc and start kind of staring at it, looking for frameworks and areas people start to agree on, and then figure out a conclusion that I can share. If it's my own answer, I just kind of start writing, and over the course of the week, I just kind of iterate and iterate and iterate, which isn't that useful to share, but it's just a lot of staring, editing, finding, sending it to myself, looking at it, continuing to edit, and then I have a copy editor.

AI assessment note: “If it's my own answer, I just kind of start writing”

Q I think the biggest question that a lot of founders speak to me about is when do I hire my first Product manager. And so a lot of this interview, I'm going to pretend to be a hypothetical, talented founder. You're going to very nicely agree with this hypothetical situation. So help me, Lenny. You're an advisor to me. When is the right time to hire a product manager?

A My first piece of advice always is you should wait longer than you think you need to. Founders often have this dream of they're going to find this amazing person. They're going to agree with them on everything. They're going to know how to build incredible product, and they could just kind of like delegate this. But it turns out that's rarely the case. Usually what actually happens is You find this person, you as a founder, you still have really strong opinions about what to build, and you've been doing it for a long time, and then there's, like, the team building it, and so this PM just becomes this middle layer between you telling them, hey, I really think we should build this, and they're like, uh, do I have any autonomy? Do I have any way that I can actually inform what we're building? You're just telling me what to build, and they're just, like, telling engineers what to build, and it becomes a really hard job for a lot of PMs. A lot of times, the founder has a bad time with that, too, so just, like, default advice is wait longer than you think, but the three things that have Founders have told me are kind of signs that they need to hire a PM. One is they're experiencing a bunch of bottlenecks, frequent bottlenecks where engineers or designers are just like block, waiting for them to make a decision, waiting for them to make, to review a design. So if you're finding there'…

AI assessment note: “My first piece of advice always is you should wait longer than you think”

Q table, actually. Say I'm a product manager now, and I'm going in for an interview, and I really want this job. And I sit down with you the night before and I say, Lenny, help me. What are the big mistakes that I should avoid in these one-on-one interviews? Are there common red flags or fuck-ups, if we're doing UK terminology, that PMs make when being interviewed in these one-on-ones?

A One mistake that PMs often make is jumping to a solution. When someone asks them, how would you approach this? It's just like, here's the answer, versus asking questions to better understand Context and the space and understand things that the person maybe hasn't shared and is kind of expecting you to ask. So a lot of what a PM is great at is breaking down the problem and thinking through all the ways that you could approach it. And so you want to kind of show that you can think through it. And like I talked about with the kind of the map of ways to achieve a goal, just like how do they map that in their head? I think that's actually the most common challenge PMs run into is just like jumping straight to here's the solution and I'm not going to really explain why.

AI assessment note: “One mistake that PMs often make is jumping to a solution.”

Q One thing that will determine the feedback that you get and the direction of the meeting is who's in the room itself or in the Zoom call itself more appropriately these days. How do you think about who should be in those reviews?

A Generally, the real thumb is it should be as small as possible. The more people in a meeting, the more time everyone's spending, the more just things start to come up. But broadly, who's involved in the project, I think is a simple way to think about it. If it's like 10 engineers, you don't want to bring all 10 engineers. You could just bring a representative of engineering or the engineering manager. I think things maybe have changed with Zoom and remote work, and maybe it's a lot easier for a lot of people to come and just kind of stay on mute and listen. The rule of thumb is you want to make it as small as humanly possible while making sure people that need to hear that feedback are in the room.

AI assessment note: “the real thumb is it should be as small as possible”

Q What causes teams to lose confidence in a PM?

A You know, making bad decisions frequently, being a little too strongly opinionated about something, and not listening, not paying attention to what the team is telling you, those sorts of things. That's actually probably the source of most of the challenges people have with PMs. They just don't feel like their voice is heard. A PM, by default, can kind of drive the ship, and it's easy for them to just be a I know what I'm doing. Leave me alone. It's really, really important as a PM to, for everyone on your team to feel like they can contribute, that they can inform what's happening. They can help. Their opinions are valuable. So that's the kind of stuff that really kills trust is not allowing for that.

AI assessment note: “making bad decisions frequently, being a little too strongly opinionated about something, and not listening”

Q Couple of questions there. How do you know when something's not working? And what I mean by that is how do you give it enough time out in the wild to get enough data to know it's not working versus pulling it too soon?

A There's something actually Airbnb is really good at is there's always this reevaluation process. Every maybe six months early on, especially of just like, are the things we're doing right now really the most impactful, important, biggest opportunities? And if not, let's just work on other things. How this played out is we were working on this for like nine months, launched a quick version of it, and I'll talk about the metrics a little bit, but the founders just kind of decided this is cool and great, but we think there's actually a much bigger opportunity in a few other parts of the product, and especially investing in our host versus like finding things for guests to do. They just decided, okay, we're going to Pause this thing for now, and we're going to go work on other things, which was really sad, but coming back to one of your early questions, just what is Airbnb really good at? It's just like not continuing down a path just because you've started that path. Rethinking, what's the biggest opportunity we can take on? And then to answer your question very concretely, the metrics were just like not great. It was like less than a percent of travelers in Airbnb were opting into this thing for it to impact the business. It would have to go so far beyond that.

AI assessment note: “Every maybe six months early on... less than a percent of travelers in Airbnb were opting”

Q Did you think it was enough before you started investing?

A Yeah. There's always this sense that, like, really great products people love and use, and I think it's more just continuing to see how that's so, like, secondary, maybe even tertiary to a few other things. Specifically, are you actually solving a problem people want? That's the fundamental element of all these things, and if a product is incredible but not solving a real problem, like, it doesn't matter. It's gonna die. So that's something that I've learned to look for really closely. And then two is, does it have some kind of distribution strategy that can get to people at scale, whether it's Virality, or SEO, or paid growth. Something that can build a sustainable growth engine. I don't actually pay attention to the product as much as I used to, because I've seen these things are much more likely to kill it, and then I'm like, okay, cool, now let's check out the product and see if it's awesome.

AI assessment note: “Yeah. There's always this sense that, like, really great products people love and use”

Q What are the questions which are most revealing of customer data that you do want to ingest versus don't want to ingest? Bad example, what do you want us to build? What's the right way to ask the question?

A So if you think about these three kind of Time horizons of how you use product. There's things you've done in the past. There are things you're maybe doing now and things you might do in the future. A classic rule of research and talking to customers is you never want to focus on what people might do because we're really bad at predicting what we will do. We think we're going to go to the gym. We don't. We think we're going to not buy a gadget. We end up going and buying it. We're just like really bad at predicting our behavior. And so what you want to focus on is what have you done in the past? What problems have you had that we can maybe solve for you? What are the issues you've had with this product that maybe we can fix? So it's a lot of watching people use a product and then asking about things they've done in the past. There's a really great book about this topic that if folks want to dive deeper called the mom test, all about how to properly do user research. And it's called the mom test because your mom will always be really nice to you. She's not going to tell you like the truth about what's wrong with your product. And so your job is to get past that and get real insights about what's really broken. And there's like a whole list of questions in that book, actually.

AI assessment note: “what you want to focus on is what have you done in the past?”

Q Can I jump in there? Who do you invite into the project to witness this and be part of it? And then like, how do we ensure that we really stress test their thinking in those questions?

A So it depends on the size of company you have, but basically you want to invite the people that will be working with them in the future as much as possible. So an engineer, Engineering manager, then the designer, maybe another PM, the hiring manager, user researcher, if you have someone like that. So it could be like, you know, three, four or five people in terms of stress testing them. You just, if you do this enough, you start to have a set of questions that you know are going to be interesting. And so you start to kind of build a habit of like, all right, this is going to be a thing that'll make them think a little bit deeper. Personally, I hate putting people on the spot with a really hard task because as a PM, you don't need to be like on the spot solving really hard problems. You have time to think. And process and research. That's why I like to give them time to think about this thing, not just like, cool, design the solution on the whiteboard now and go.

AI assessment note: “basically you want to invite the people that will be working with them in the future”

Q I do want to ask you, we've covered kind of the nomenclature. We've covered the hiring process. In terms of the actual workings, I want to touch on a couple of really Core points. You know, product reviews are so central to really any product team, and especially product managers. How do you think through how to do product reviews?

A So broadly, maybe thinking about just problems that often arise in these reviews where a team has come to a leader and they're just like, hey, here's our latest update on designs that we're working on. I think the most common problem in these meetings that causes all kinds of wasted time is not connecting back to the problem that you're solving as a team, whether it The problem that feature is trying to solve. A lot of times you come to a product review, you're like, oh, check out these great new designs. Here's how it's going to work. Here's the flow. Here's the interactions. People start getting sucked into. It's like, awesome. Look at these colors. Oh, maybe we should move spacing here a little bit. Maybe we should move the button up here, but you lose sight of just like, is this actually achieving what we're trying to achieve as a team and as a business? Like, is this going to increase conversion of a specific type of user through this flow? Is this going to reduce contact rate? If that's what we're trying to do, is this going to increase adoption of a new feature? So you always want to come back to, here's the problem we're trying to solve with this feature. The way to do that is at the beginning of the review, you want as a team to start with, here's the problem we're solving. Just like put it up on, you know, the slide. And then if you're the leader, you want to ask, you…

AI assessment note: “at the beginning of the review, you want as a team to start with, here's the problem”

Q What do you find the most challenging element of the writing process?

A I'd say at this point, so I've been doing it for almost three years now. It's a weekly newsletter, put out a post. Just, there's always another post. Write something awesome, really excited about it, and then, alright, what's coming next week? So always imagine this, like, Indiana Jones boulder chasing me, getting ready for the next week. So it's kind of just this, like, never-ending need to write something awesome. On the one hand, it's so incredible how much this generates and allows me to live the life that I lead. On the other hand, it's like, in theory, I have to do this for the rest of my life, because people are paying me monthly, buying annual plans for the next year. I don't know how you, like, exit strategy for a paid newsletter, so I'm trying to think about that right now. That's the main drawback.

AI assessment note: “it's kind of just this, like, never-ending need to write something awesome.”

Q schedules that are perfectly kind of aligned and structured, and then you say something brilliant like that, and I just kind of go, you mentioned shaping that, and kind of the inputs and the data that one gets to really feed that kind of Product mouse and direction. How do you think about when to listen to customers and data versus when to go on pure gut intuition and feeling?

A So you should always listen to customers. I think the question is basically what should you be listening for? And what you don't want to be listening for is what are they like telling you to build and their solutions to a problem they have. What you want to be listening to is what pain points do they have that you can then think about how to solve most creatively. So as an example of That way you don't really want to listen to what people are necessarily telling you to build. One of the most common requests that Airbnb gets is, and this has come from like day one, is like, I wish I could just sort my listing search results by price. Just like, show me the cheapest one, because I want to book that. So many teams have tried to build that, and every time they launch, it's always a huge hit on conversion and bookings, because people see listings that are not going to accept them, that are just like low acceptance rate, or that are just terrible, and so they just like move on. They're like, I don't really want to book an Airbnb anymore. And so it turns out, Sorting by price is actually hurting your chance of booking a place and having a good time, and so the thing you want to focus on is just like, what are they looking for? Basically, they just want to find a place that's awesome, that they're going to have a good time at, and turns out a lot of that is smart search ranking.

AI assessment note: “you should always listen to customers. I think the question is basically what should you”

Q What would you like to change in the world of product?

A So a lot of people really dislike product managers, and that makes me very sad. I think it's because a lot of people have worked with bad product managers, and they kind of create this bad brand of PMs. My feeling is, if you don't like PMs, you've worked with a bad PM, because PMs should make everything better, should make you happier, should make you more efficient, should let you do better work. What I want to change is just like the brand that PMs are not good, and people dislike PMs and don't want PMs on their team, and I think The way you do that is you just help PMs become better and kind of raise the bar for everybody, and it's kind of what I'm trying to do.

AI assessment note: “What I want to change is just like the brand that PMs are not good”

Q How do the best in that project, how do the best structure their thoughts and outline their solutions to the problem that's been given?

A Roughly the way you want to think about it is just like, here's the problem. What are the levers and opportunities to bring us closer to solving that problem? So you kind of like think about like a tree of just like problem, opportunity, opportunity, opportunity. And then within that, how do we How do we move closer to that? So you kind of want to see this, like, little tree or web from the thing we're trying to attack to little individual things we can do to move us closer there. So there's kind of this visual you always kind of want to look for, and it's usually like three to five things that are moving us closer to that.

AI assessment note: “think about like a tree of just like problem, opportunity”

Q How do the best in that project, how do the best structure their thoughts and outline their solutions to the problem that's been given?

A Roughly the way you want to think about it is just like, here's the problem. What are the levers and opportunities to bring us closer to solving that problem? So you kind of like think about like a tree of just like problem, opportunity, opportunity, opportunity. And then within that, how do we How do we move closer to that? So you kind of want to see this, like, little tree or web from the thing we're trying to attack to little individual things we can do to move us closer there. So there's kind of this visual you always kind of want to look for, and it's usually like three to five things that are moving us closer to that.

AI assessment note: “think about like a tree of just like problem, opportunity, opportunity, opportunity”

Q founder or CEO. If one of my PM slash investors had a loss like this was, didn't work, I don't want them to be tarnished by it. I don't want them to feel a lack of confidence. How can I, as the leader, ensure that when it does happen, which it inevitably will, my team doesn't lose confidence, and they come back with the same vigor that they once had?

A I think, I think a few tactics. One is to share the learnings of this project, and not treat it like something has gone terribly wrong, but just like, hey, we learned a lot from this project. Here's what this team has learned, and You know, you kind of celebrate that a little bit. Two is you, you don't treat it like when you're doing performance reviews, you don't treat it like you made a huge mistake. It's like, okay, we learned a lot. This was an interesting project. Let's move on to the next thing. Kind of like flipping this question, actually, something that this made me think about is as a PM, something I've learned is you don't want to be so emotionally tied to a product where like you force that you need to make it work no matter what. Because a lot of times just you're asked to work on a thing and it doesn't work and it's not going to go well. And I've learned it's valuable just to kind of like, okay, This isn't working. Let's just move on to something else. I'm not like emotionally tied and personally tied to this thing working. This is something that the company wanted us to build and it's not working. Well, we tried it. Let's move on. That really helps because a lot of times teams are just like stuck. Let's just make this work. We really need to make this work. And if at some point you're just like, okay, it wasn't like even our idea. A lot of times I was just trying…

AI assessment note: “One is to share the learnings of this project, and not treat it like something”