Unorthodox PM wisdom: Automating user insights, unselling job candidates, logging every decision, more | Kevin Yien (Stripe, Square, Mutiny)

25:01Or is it just, was it just like obvious to everyone we need to spend as much time as we can? Top down everyone knew. I definitely know that 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. And there's this other aspect that I think PMs like to feel good about how dizzy they are.

25:43I'm like, I'm involved in so many processes, and I have to talk to this person, talk to that person. All that might be true, but I think there needs to be a calibration or at least like a spring cleaning of what's everything I'm doing? And 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. And I think we just all have to have like hypersensitive intent onto 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, It's also a problem.

26:27It's amazing. Reminds me of your now colleague, Jeff Weinstein's advice he got from one of the call -sons where they came to him and they're like, you're a world class that 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. Totally. I will say so one on that, the CDO and Mutiny, Charlie, she always repeated to me non -stop, keep the main thing the main thing and would just say it ad nauseam 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.

27:12You can't say oh I'm only focused on this thing over here so other folks handle that. Like you do have to figure out how to do a little bit more at the same time but So, prioritization does play a factor. There's a framework Shreya suggested that I really liked the L &O framework. I forget exactly what the L &O stands for, but leverage something, something and welding too in the show notes that gives you some advice on how to prioritize your time based on the stuff. Totally. 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.

27:45I will convince people when you make more time for that. But I don't want to make it seem like it was me against everyone because I was something not the case. I think the starting engineers and designers on that team really cared about the quality of what they built to. That's a pretty structural sort of DNA for a team as well. If you don't start with that and as a comparison, you have a team that is 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 wanna push on this stuff.

28:25So I do think you have to take into account like 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 put into effect if you believe that it's worthwhile? Let's go back to the perimeter, or drawing the perimeter concept to make that a little more real for people. So advice here is the role of a PM, kind of your main party or main job. Especially when it comes to engineers and designers to draw the perimeter. For the team, can you make that a little more real? It's an example that maybe from something you work on, what does that look like?

28:58Totally. 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 like stay focused on this point of sale example, one constraint would be with the Halloween 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.

29:40There are 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. And it's just about how do you remove decisions, right? Because this I think is like a maybe a fright phrase, but the best decision is no decision. Like if you don't even have to think about the decision, the team is that much more effective. So to 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.

30:12So you mentioned there's make sure the user is clear who you're designing for. If there anything else just like thinking about maybe the PRD someone's trying to write to help create this constraint, whatever maybe bullet points sections would you imagine or do you find useful to add? So beyond customer segments, laugh 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 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 etc?

30:58And 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? And one example there might be speed. And so if you say speed is more important than consistency of data, that's a huge trade -off and constraint that you can give the team, oh my god, if an engineer here is, I don't real -time consistency of data, I can do so much cool stuff and easily accomplish that speed thing. And so that's just like a very technical example maybe. Awesome. Okay. I'm glad I followed up on that.

31:37There's a couple more things you mentioned that I want to come back to you 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 like a rough quick draft. I find with design, especially if you design something ugly and designers are. and like, let me make that better. You can't stand this thing. Is there anything else you want to have there, just like this idea of a tuning fork as a feedback strategy? Okay, there's two areas we can go deep run here. One is in how you get the feedback.

32:09So this is definitely a squareism. 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 try them 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. And we're not going to talk. I'm literally going to force us into a room or zoom.

32:54You'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 rev on this thing and get to the next base. 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 meeting and the meeting is for you to spend time reviewing this and giving me feedback and then maybe we could talk about it. 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.

33:25Why 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 Bots are a little bit better in crisper And I think with this idea like 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.

34:01I'll give you feedback. I promise give me give me 24 hours Right, it's not like they have to come to this meeting Although I would urge you to make them come to the meeting. Okay, say more there because you find that that's a lot more effective 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. Like maybe you'd 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 dog at the same time. I think this is the part that often gets lost, which is the latency between a comment answer 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.

34:48And so when people are trying to find out like how do you move faster, like this actually is one of those very good examples of moving slower to the faster. It reminds me of Claire Boe. 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 just like 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.

35:23The first is something you call decision log. You think every PM should keep a decision log. Talk about what that is and why that's powerful. I will say there's sort of 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 purity, 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,

35:58every person has something that they can do to slightly increment in their craft. And, you know, 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, like you're still doing your scales. And it's because it lays the foundation for everything else you need to do. And so we all talk about product sense. It's this like super mystical thing that no one knows how to get better at. But to me, it's just a fancy way of saying you can make good decisions with insufficient data.

36:34And 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 follow -up 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. Those 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. Those other companies that are doing crazy things, what are they doing? What would you do if you were responsible for the roadmap?

37:11Write it down a year later, see what they've shipped. Like, 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. It's just doing more of them. I'm hearing you describe this, it feels like obviously, yes, why are we doing this? Like 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 decisions still, maybe shouldn't be. So I guess first of all, do you actually do this? How often do you do this?

37:44And is there an example of you learning something from your own decision lock? 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 like the perfect note taking system to me. The best note taking system is inspired by what is it called? Like big ass text file, BATF. There's a funny blog post from like 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 on one big note. And that way you can, you know, command F bit, do whatever you want.

38:24The way that I keep track of it is I do all like hashtag decision and then write things down just as I think about them. And then I'll have a reminder to set a comb back through on some cadence. And so I'll first use a positive example, which is a funny one. So it'd be rewind to, I don't 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. 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.

39:07Like they have completely hijacked this specific loop for consumer buying behavior via this very unassuming thing Which is package tracking and so like that morning. I was like, you know, whatever I'm gonna quickly draw a diagram of this flywheel that I think Amazon owns today I'm gonna show how Shopify is like slowly Planting their little seed to take over this and how shop that fits into it I tweeted out and then I don't know that day There must have been like 60 Shopify and employees that followed me and 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.

39:46Here's what we were thinking, here's why, you know, 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, and 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 like one interesting example. It's an amazing story. You doing this explains why you've been so successful. I can see how the soul connects now.

40:19I think up for a lot of people they want. They would want to build this habit. Like clearly there's a lot of value here, but they just don't because they get 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 slash decision log that you think might be helpful to folks to motivate them to give this a shot. This is probably just general advice on building any habit, which is Start small and just force yourself to do it and There's like that old saying around How do you start running as a hobby?

40:55You don't do it by saying I'm gonna 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. Like 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 like you build up to that thing. And 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 gonna scroll through Twitter, I'm gonna check out hacker news, whatever it is.

41:29I'm gonna see something interesting and I'm gonna make a bet. I'm gonna 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 like constantly writing these decisions down and then it's like feeding its way back into you. It becomes second nature. And you're touching on something that There's been a little bit of talk on this podcast and these let her post about this idea of to get better product sense and product taste and also just like decision making this case.

42:04One 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. 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 an 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 at it 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 getting any better.

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43:56Check out Epo at Getepo .com slash Lenny and 10X your experiment velocity. That's Getepo .com slash Lenny. If someone wants to try this idea of a daily log, what is it exactly? Say decision log or a daily log? Is it just things that happened 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? Yeah, it depends on how far you want to go down productivity and not taking start rabbit holes. But let's start basic. This is not what I do, but I think it's the easiest place to start. Spend up a Google Doc or a Notion page.

44:32Just call it daily log and then bullet point out like 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 you know like the fulfillment to buying behavior loop. The reason for that is XYZ follow up on this in six months and then set your calendar in bite. Awesome. So as motivation for listeners to try this sort of thing. Just look at the success Kevin has had in his career and how insightful he has been so far and will continue to be.

45:11And this is how these happen. This is how your mind learns to see things in a really unique, interesting way. So I know, I know you're modest and aren't going to take any credit, but I'm just saying this is how you, the sake of better, is trying stuff like this. Footnote correlation versus causation. It's all put out there. Could be all genes could be completely unrelated to anything you've done in entire life. I see. It's been me being very lucky. I'll put that out there. It'll also be like, 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 something like this.

45:46I 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 signal, 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 and form? It was all at all a leading indicator of anything. And I feel like this is a really good method for improving your interviewing abilities. It's like, here's the question asked. Here's what I decided.

46:13Here's what I think, and then a year later, look back. Is that actually your aim? Yeah, totally. I think some of the best companies actually do have a practice around this where they had a 6, 12, 18 month check -in on new hires. and they then compare, you know, their sort of performance against level higher than and then review against the score cards. It's like a pretty laborious process. So, you know, startups aren't probably gonna 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. I love that, oh my god.

46:51It puts all this pressure on your score, which is great. So let's actually segue talk 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 an 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. I'll say the idea of the unsell email came from a place of failure, which is at Square, I had sort of shifted into a position where I had to hire a lot of people really quickly.

47:22And through that, as a, you know, rather than you hiring manager, you're like, all right, great. The goal, 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. And 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 stuff like, yeah, and this person's really good. And you will see, like, they are pretty good, aren't they? even though there's a sneaking suspicion that maybe they're not the right bit, but you move forward anyways.

47:54So 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 then 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 is 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 like interimmobility or something to another team, which then leaves you with the same hole.

48:34So all of those bad outcomes, somewhere, how do I prevent this? Well, I just got a front load, all the gnarly stuff they're gonna find out in their first six months. And so the practice I started developing is you go through the whole interview process and during that period You're collecting all these little concerns, fears, anxieties that they're not explicitly saying but they're definitely hinting at and 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 April Appoints and I say say all the terrible things that are probably going to reinforce their fears.

49:14And I'm pretty tainted 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, right? 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, that you can occasionally hop on a meeting on a Saturday or Sunday. And if you can tell them that up front, and they can read that whole email and still be equally excited to join, you find yourself any plus higher.

49:58But 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, then have them lead after six months. And when I first instituted this, I lost 30 % of candidates at offer stage, which drove my recruiting partners insane because they look terrible. They're managers 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.

50:35And that's really crucial, I think. But once you hear it again, this is like 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, we all, the socks for them, but at a macro level, this is good for the business. And they're like, all right, let's keep doing it. 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 stock you from setting an email, technically.

51:08I'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. Yeah. And in theory, the incentives would be aligned where the recruiter success matters, is based on like, did they actually have a good time? Did they stay? Did they have good impact? But, typically. And, obviously, their incentives aren't right. I think some companies have shifted on that where recruiters and sort of salespeople are compensated sometimes in similar ways, on terms of like quote or whatnot.

51:49And so they'll hold the recruiter accountable to, you know, 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. Okay, so the advice here is to end up with better people that end up being successful and happy put together, like 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 may be a problem if you join, and I just want to be very upfront about it. I think you actually shared template of one of these emails on your blog posts.

52:25Yep, that's right. I have a fairly real one in there. Is there anything else hiring wise? I know there's probably infinite things that you've done, but is there anything else you think maybe worth sharing of things you've learned to be more successful at hiring awesome people? One funnel on the on -mic and on -sell email is, it's not as if you just send the email and then they either say yes or no. Like 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, like you need to bend to do whatever it takes for them.

53:14And 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. And that sort of has to be the place you get to for like really strong hires. So that's just like 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, you know, if your quote -unquote organization is hiring a hundred engineers or whatever, You have process around it, you have pipelines as a machine at that point, but I do think the direct hiring managers have a responsibility to be really involved in every individual.

53:53Because there's no one who's directly hiring 100 people. It's always within a number that I think you can take on. Okay, so this is the final tactic that I heard you're amazing at, which is automating user research. On the surface, that 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? Let's start from why this even matters. I think a lot of folks going back to what is the point of product management?

54:24I 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 hell with that. Like, I know PM should settle or 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 why I think like, you just need to constantly be talking to or interacting with whoever is your customer, that's like the foundation.

55:08So 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 sort of but you need to fix that in order to even get close to the next thing. So, 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.

55:48There's so many good resources out there right now. And I think that there are, I'll speak mainly from like 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 a thing called user -interviews .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 stay stream of the exact ICP you want to go after.

56:22ICP 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, whenever you want. I don't care what PM you are. it seemed like you can find the terms that are associated with what you care about the most.

56:59Those then get pushed automatically to a Slack channel or otherwise. And then you can set up workflows either via Zapier or something else to say, who was the customer, pull their email, put that into a sequence, drop in my calendar, and you just have interviews showing up automatically in your calendar. I will say I cannot take credit for this, shout out to Beth Hills, who was a PM that I hired in Mutiny, she is the queen of automating customer research and like built in a amazing system around this. So the way it works is you said a term for like, I don't know, a POS point sale something in Gong and if somebody says that or has an issue there, talk about again how that schedule is a meeting with you potentially.

57:42Yes. So Gong has an integration with Slack. you set up this alert, it posts a 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's Burger Lenny's at Lenny's Burger Shop .com. And then you can set up a Zapier to take every new Slack post from that and then send using customer IO in email to that person using that field. and then in that template of the email, drop in your calendar specifically for user research. Wow, that is genius. I love that. There's another similar tactic that Theresa Torres shared on the podcast when the early episodes where you have a little pop up on your homepage asking people, hey, do you wanna talk?

58:34We'd love to hear feedback on our product. Click here if you wanna give us some feedback and then that schedule is a calendar on the PMs. Totally. The PMs calendar. So you mentioned Gong, customer, yo, So there's like some tools here. Is there anything else you think is that Zappier? Obviously, is there anything else you find useful to help automate the sort of stuff? If I take a step back from the automation side, or maybe like straddle it, depending on 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.

59:13There 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 bid. If you can take advantage of that, you can usually set up something. And if it's not a gong or a zappier, maybe it needs to be just like a custom script that you write or you sit down with an engineer and say, like, how do we set up a learning around this thing so that I know when things are happening? And I think you can't use the effort required to do that as an excuse to not be talking to your customer more frequently. Because again, if we go back to a product manager should be trying to convert this potential into kinetic energy.

59:51Part 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 line cook and then standing with a line cook. You will just pick up on so many ancillary aspects of what their life is like that cannot possibly be communicated in like a report and you owe it to yourself as a PM to be exposed to those things all the time. In my experience every time I talk to a customer I'm always reminded why have I not been doing this more. Like, how can I not be doing this?

1:00:35It'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 challenge issues. I'm reading their emails like I get it. Until you actually talk to them, you're like, oh, wow, I had no idea. And 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, it's you are talking to a potential customer. It's not just reading a cool feedback that they share.

1:01:07That's right. And 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 like budding with energy to do this. Like 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, you know, 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.

1:01:49Because the world is changing, their lives are changing and you need to constantly be exposed to those little microchanges in their lives in order to build the product that they'll eventually need. The best explanation I've heard of this is actually from your new boss, Patrick Halson, boss's boss's boss. I don't know how far away you are from. 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 model of what the customer needs and then that informs what to build.

1:02:22100 %. 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. There's plenty in work. I don't know if any of them are interesting or novel. I feel like everyone's just like figuring it out in real time together. So I'll actually take us in a slightly different direction and this maybe isn't directly useful to product managers But I think it's a really good story.

1:03:02So when mid journey 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 like I have three daughters one of them's seven years old and so her and I were awake we were waiting for this to wake up and I was like, oh, I have this cool new thing. Do you want to play with me? When 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, you know, unicorn prancing in a field.

1:03:41And it generates this hideous looking, like, demented unicorn with two rear ends, and like a demon flying over it. And I'm appalled at first thinking that she's gonna feel really bad about what she got shown. But instead I look over and she's an awe. She is amazed and then she turns to me and she goes, did I draw that? Like, 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, did I draw that? And 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.

1:04:38Like 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 chatter? Is it something else? Like, 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 trying. but kind of damn it, like 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.

1:05:18But all I can say is we are not even like beneath the dust on the surface when it comes to what's gonna change. Well, that is an amazing story, give me tingles. It makes me think a little bit about how like we used code in binary and then like assembly and now it's you know Java and then I don't know. All the languages Python and now it's like it's like code like AI, LLM's generating code and it's the same thing for drawing potentially used to be stick center cave and now it became crayons and pens and iPads and all that stuff and outs again LLM's. So that's pretty bonkers. amazing story. Thanks for sharing that useful to PMs and non -PAMs alike.

1:06:06Okay, I'm gonna take you to another recurring corner slash segment of the podcast fail corner. I am curious if there's a story of failure that you can share of something that then go the way you want it and still had a positive impact in your life or career. Well, there's countless stories of failure but I'll 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 the end of my way to PM. I land my first official by title PM job at a startup.

1:06:53I made it. I've arrived. I'm officially a product manager. And we go off, 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 four or something. And 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, I couldn't get past that.

1:07:37And so, for what's worth, this is the one post I have on my website that I actually feel like 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 together ended it, it helps even myself sort of get back on the horse.

1:08:28So, 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 in 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 Wantsow is 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, like I know I'm good, I think I'm good.

1:09:17And I am going to prove the hell out of that, mainly to myself, but ideally to other people too. And I think, you know, you shouldn't do things for other people for validation, but the initial success I got to see and like 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 continue to build, you continue to grow. But I think right now, the market's weird.

1:09:55The market's wonky. There's a lot of really good talent that is just getting hit over sideways. ways. And 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 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 truly out of your control that you can now apply to find a better fit.

1:10:36And that's one of the big things that I've been able to, I think, come around to you. 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, you know, 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 real evaluate what parts are actually part of your identity and which parts are in your control to change and whatever you do next.

1:11:22Well, what an important and great story. There's a, as you mentioned, a lot of people are dealing with finding it hard to find a new gig and a bunch of layoffs. And I think this is gonna help a lot of people. The two categories you share to 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 am not good at these skills. You just share those two kind of things that might be true that you may not be recognizing about why you may maybe Lajjo again. Totally. So one is the business just as I have a need for you. You know, they got ahead of their skis and that's their fault.

1:11:57And 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. And this one I think is really, really important because I've seen so many times where there's been a PM engineer designer like 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? Like maybe a little bit, but honestly it was just a change in environment and when you find the right environment in the right role Like you just flourish.

1:12:39And I think this is actually sorry. We'll go back to hiring for just a moment or at least management 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. And 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. Like 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.

1:13:24And that's empowering. 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 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. Uber is very different from every B. 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.

1:13:56Like what habitat are you creating for your come for your employees to enable them to think differently to or to be shut down and not feel like they can be creative and try big things or not. And And basically the way it just kind of delivers that metaphor, like you may be a palm tree and you're trying to join Antarctica and it's not going to, it's not going to go well. Totally. You got to find Palm Springs or some heart place. Kevin, this has been amazing. Okay, so before we get to our very exciting lightning round, is there anything else that you think is important or valuable to share, or to listeners with and if not, absolutely?

1:14:30I think we'll probably find ourselves on interesting detours to the lightning round. So let's roll in. Kevin, with that, we reached our very exciting lightning round. Are you ready? Hell yeah, let's do it. Let's do it. Question one, what are two or three books that you've recommended most to other people? 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 like 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?

1:15:16Like impossible, but you can read and pretty much get the same thing. So anyways, strong requirement or strong suggestion go read like autobiographies and memoirs of people that you respect Mostly for like their their mental model and way to approach thinking less about you know 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. Yeah, but It it covers. It's like a very secratic method style. So it's about a philosopher and a young person And it tries to teach you the ways of Eulerian psychology, which is sort of like counter to Jungian theory.

1:15:57The reason I really like it is because it makes me uncomfortable. So the whole premise, in my opinion, behind the book and Eulerian psychology is focus on what you control. Like 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 like be the person that you think will attract other people that you want to be around and There's some like really pointed notes in there that I'm like, ah, I don't fully agree with that one But it always pushes me to question something about what I believe and so In every like physical cognitive of book I have I like write the date that I Started reading it again and you know 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.

1:16:55Wow. It's like a decision -log in another context almost. Yeah a little bit. Honestly, the other book I was going to mention is the paper minasurine. This actually shot 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 sort of loud on Twitter in a very good way. And I think I learned a ton from stuff that you would post. But one of the things that you posted was this book. And it is just the most beautiful collection of essays that span like sci -fi and fantasy. And so like if you're into that kind of stuff, if you like exhalation, then like Pippermint Asheray is even better.

1:17:39Oh shit. Guess I gotta add this book to my list and do you love exhalation? There you go. Oh man. This job is tough. I get to learn all these amazing books and then I get to read them, but I don't want time. Hard. Speaking of more time, next question, do you have any favorite recent movies or TV shows that you really enjoyed? There's less time for either of 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 if like seeing the details that they do. actually gives me a lot of anxiety, but I really appreciate the craft they put into it.

1:18:16The other show actually, this is, I think this is the first time, physical 100. So this is a Netflix show. It's a Korean show about, you know, a hundred different bodybuilders, athletes, what have you want to go as like the often living 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, like 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.

1:18:59Like 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 like bowing and like just humble to compete against the guy. I kind of wish that more American shows had like that level of respect as opposed to just like trying to find the most conflict. There's something that I really like about that. That's beautiful. I've started that show but I haven't continued it so I'm going to revisit it. Do you have a favorite product that you've recently discovered? that you really like. We got a really old 2002 Jeep to work on with my daughters.

1:19:38I just like a true junker. 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 clicking hair clips or whatever else so magnetic trays shout out and then selfishly I will say My buddy Arjan Mahanti has an app called circuit if you search the app store for circuit like CIRC UIT Hit timer. It's such a delightful little app that lets you track like Tabata sets or whatever else to just get like a little look at it Super cool.

1:20:25And that magnetic tray is not boring at all. That is extremely cool. And that is a really cool story too. Do you have a favorite life motto that you often come back to and find useful, share with friends and family and work your own life? 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. and I hated that growing up because she only said it when something bad would happen.

1:20:57You know, something that happens, 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, ten 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.

1:21:44So 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 seven year old. I come home with my math test one day. The guy at 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 %? Oh, right, God. I'm just like distraught. And I soak away. I'm very sad. I study hard. I do the next math test. I get 100%. Yes. All right. Dan's approval. Here we come I come flying back. I put the test in his hands. He's serious on his nose at it looks at me worth another 3 % I'm so confused.

1:22:31I'm like I got a hundred out of a hundred. I have no clue what you're talking about He just looked me done the eye and goes who said a hundred is the most you can get

1:22:42At that age, I literally had no clue he was talking about. And he had to reframe it for me in the moment around, like, what was their extra credit? Who set, like, 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. And I think I carry that beam forward where there's this weird transition you 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 hundred percent of what your job requires, you'll never grow.

1:23:26And so it's up to you to actually find what is the additional three percent. There's always three more percent. So that's my dance lesson. 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 founder companies, 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 have guessed that you're a competitive eater at some point in your life.

1:24:04As a final question, what the, tell us about this part of your life, what did you eat? How does this work? How far did you get in this path? It's probably misleading to say that I was like a true competitive eater. Like I wasn't on the circuit with, oh, I was forgetting his name, but Johnny Chestnut. Oh, yeah, Chestnut. Back in the day, that's like the OG competitive eater on the hot dogs were good, I guess. For me, it was more eating challenges. And so whenever I would travel, I would find like the local eating challenge, whether it was time -based, volume -based, something else, and just like try to see what I could push my body to do.

1:24:39I was blessed with a great metabolism, so I never really had to worry too much about anything else. And the origin, like 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 Manys, which is where like the Vikings front line goes to after every game. and they have this ridiculous 97 ounce quarter house. I don't know how many pounds that is, but it's too much for a human to consume. 97 ounces, yeah. And so I sit down, I order it thinking, this is gonna be great. They put it in front of me, it's a monster. And 40, you have to eat it in an hour.

1:25:19And 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 clouded 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, Anna carried for nearly a decade of trying to do these interesting challenges. Wow. I don't know how that's physically possible, but clearly you did it. Kevin, this has been wonderful.

1:26:04I think there's so many lessons here for people in so many ways life and work and parenting. Two final questions. We're working for, it's fine. If they want to follow you and learn more from you over time. And how can listeners be useful to you? I'm on Twitter, just at Kevin Yen. Technically, I'm on LinkedIn, I don't post it or if. I probably should. I hear it's very good. But that's where you can find me. I was on 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.

1:26:41So on one hand, I love all the different websites, the others that exist. It's amazing what we've sort of 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, wide -by -line. And so like my website is like, it's a GitHub page, it's also not GitHub pages, but it's just raw HTML, CSS, nothing fancy. And I get so much joy every year just doing like 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 gonna write anything on it, you're never gonna share it out just Oh, no little piece of the internet.

1:27:26It feels good I love that I didn't know that about your website and I could see I could see it now as I go there like it's dot html Which you don't see as much anymore? And then yeah, I can listen to it's useful to you. This is gonna sound right and it has nothing to do with product necessarily really? Just be kind. Like 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.

1:28:06What an incredibly beautiful way to end it, Kevin. This was so much fun. I'm so glad we Thank you so much for coming on. Thank you for having me. 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 a leaving review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at Lenny's Podcast .com. See you in the next episode.