Lenny's Podcast: Product | Career | Growth - 4 questions Shreyas Doshi wishes he’d asked himself sooner | Former PM leader at Stripe, Twitter, Google

Starting point is 00:00:02 Today, I am super excited to bring you a very special episode with Shreos Doshi, recorded live at the Lenin Friends Summit in front of a thousand people in San Francisco. This is Shraeus's second time on the podcast. His first visit is the third most popular episode of all time of this podcast, and I love that Shreas was game to try this. In our conversation, Shreyes shares three questions plus a bonus question that he wished he'd ask himself sooner in his career. We talk about why product leaders are so busy, why the job is so frustrating, why it is. is so essential to build good taste, and also why you're probably not listening as well as you should be. This was so much fun.

Starting point is 00:00:39 A huge thank you to Shreyas for doing this. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes and helps the podcast tremendously. With that, I bring you Shraos Doshi. Shraos, thank you so much for being here, and welcome to the podcast.

Starting point is 00:01:01 Thanks, Lenny, for having me. This is amazing. I was going to ask. We recorded our first time. episode, I think, two years ago. And I was like in a tiny room in my house. I don't know what you were, but it was very not like this. Thoughts on the setup of this episode.

Starting point is 00:01:18 So first, the Lenny Empire keeps growing, which is amazing to see. And second, as I was coming up here, somebody told me this used to be a car dealership. And I actually realized I purchased my car here. What? So crazy. Only in SF. What kind of car was this? Say more.

Starting point is 00:01:41 It was a Honda CRV. Okay. Wow. I'm told this venue is also used for Jimmy Hendrix performed here and Aretha Franklin performed here. So we're in, it's like Jimmy Hendrix, Aretha Franklin Shreyas. There we go. That's going up on my Twitter bio soon. Okay.

Starting point is 00:02:02 So usually when we talk, you're full of... full of ideas and you're full of answers. When we were preparing for this, you told me, I have questions. I have questions I want to ask. You know, reflecting on my career as a PM leader over the years, there are some questions I wish I had asked myself sooner, but I did not.

Starting point is 00:02:33 And I had the great luck of having a life, a PM life, full of suffering. And I have zero complaints about it, but as I look back, I feel like there are some questions that I wasn't, even if I asked myself some questions, those questions I wasn't honest to myself about the answers. So that's what I thought I'd do is kind of share the questions that I wish I'd asked myself sooner. Awesome. Yeah. Yeah. Okay.

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Starting point is 00:05:26 and get $1,000 in credit on their pro and enterprise plans. That's us p-a-r-g-on.com. What's the first question? Right. So let's see. The first question is, why am I so busy? Why am I so busy? And the background is that, like, you know, I have spent most of my career just being completely stressed out. Just absolutely stressed out every day. And there were many reasons for it. But one of the core reasons was I was always super busy. And there was always work.

Starting point is 00:06:12 I felt like I couldn't do that I wanted to do. And so I would go home at the end of the day and even if I had worked hard, I just feel dissatisfied. And so that was a constant fixture of my life as a PM, PM leader. And it's only... So I did product work for about 20 years before I started this new chapter of my career. And I think I only fixed it in the last three or four years of my career as a PM leader. But that means that there were about 16 or 17 years where I was just incredibly busy. And because I was incredibly busy, I was extremely stressed.

Starting point is 00:07:00 And even though I was doing a good job, I was not feeling very good inside. And then that showed up in my body, like all sorts of pains and aches, I realized were actually not physical pains and aches. They were pains and aches from the stress. It's like health issues that you had. Yeah, yeah, minor stuff. So, you know, I mean, relatively minor stuff. But, you know, like playing tennis and you pull your back muscle and now you are horizontal

Starting point is 00:07:26 for three days, doesn't feel good. Who here is very, very busy and is just way too busy. raise your hand. That's it? Yeah, I know. Whoa. Everyone's like, everybody. Yeah.

Starting point is 00:07:40 If you're like, yeah, yeah, I don't have to raise my hand. I'm busy. Yeah. Okay. Keep going. Yeah. And so here's the thing. You know, when we talk about being busy and managing your time, energy, all of that,

Starting point is 00:08:00 I mean, this is a group of senior product people. So you all know that take tips and techniques, right, like maintain a to-do list. I found the L&O framework very useful for me, which I've shared before. You know, I used to like working out of a calendar, those types of things. And I think you're all familiar with those things. But what I wanted to call out is that at some point in our product career, we reach something. We reach an immovable force that will just overwhelm us, no matter what we do. And that force is scope.

Starting point is 00:08:43 Okay, so as we grow in our product career, our scope grows. And we kind of like that, which is all great. But at some point, if you haven't already gotten there, many of you have, but for those of you who haven't, you will get there, where your scope will be so large that no matter what you do in terms of, efficiency, whatever framework you use for prioritization, whatever framework or tool you use to manage your to-do list, whatever tools and techniques you use, whatever prioritization you do, your scope is so large that you are still going to be incredibly busy. Right?

Starting point is 00:09:21 And so that's what I faced, like I was saying for the first about 16, 17 years of working on products. And only in the last three or four years was I able to be able to be able to do. able to kind of find some answers on sort of how to deal with that school. Right. And so perhaps we can talk about that. What do you think? Yeah.

Starting point is 00:09:43 So you're basically saying there's all these productivity tricks, ways to do more faster. And no matter how many of these tools you've got, you were just going to take on more and more work and they'll peter out. I'll say many of my most popular news that are post are, here's productivity tricks and tips. Right. And so people are always looking for these.

Starting point is 00:10:01 And I'm curious to hear where you go with this. That is not the answer long term. There's a different approach. Yes. And so the challenge is the following. How many of you are going through some kind of annual planning right now or you're planning on going through annual planning? Everybody loves annual planning.

Starting point is 00:10:21 Great. So let's take annual planning. If you are like a high-level manager, leader, within a company, what is the typical kind of, what does your month look like? Or in some cases, unfortunately, what do your two or three months look like when you're going through annual planning?

Starting point is 00:10:42 It's all these kind of like spreadsheets to fill out and meetings to have and dependencies and priorities and stakeholders to meet and so on. And so I noticed, for instance, that at some point that was making me really busy. And then that was making me feel guilty now because I had my like team to look after and to support and then I had you know product decisions to make and various other things and I've gone on some like you know planning retreat or whatever And you know there you go you last four five six weeks like does that sound familiar to folks like am I? Yeah? Okay, so So I noticed that I needed to change that at some point and

Starting point is 00:11:29 actually found a solution. Again, late in my career, but I found a solution because I asked myself this question, which is why am I so busy? I'm doing all the efficiency things, I'm managing my to-do list like a champ, I have my calendar set up just right, I have my routine set up just right,

Starting point is 00:11:44 I'm working out so that I'm engaged at work, I'm productive, I'm doing all of that. Why am I so busy? Oh, it's planning season. And that is supposed to take up four to six weeks. And this was at Stripe when I encountered. So that is supposed to say it's take up four to six weeks. Well, I realized that you don't have to do that.

Starting point is 00:12:07 Right. And so at some point in my time at Stripe, what I realized is the following, right? Like we go through a whole kind of all sorts of, you know, just rituals around planning for four to six weeks. Then we emerge and we share our plan with our executives. They ask us some, you know, you know the questions they're going to ask. they're going to ask like if money were no concern what would you do what what is your ambitious plan so if we gave you five more engineers what would you do what other things would you include in the roadmap right like the standard stuff right and so you emerge you do your presentation and then you publish the plan and then you start the new year with a lot of enthusiasm and a lot of excitement and January goes fine until you get three customer escalations for features that were not in your plan, right? And so now you try to figure out how you're going to revise resources, you go talk to some dependency team that's going to sort of, you know, support these new features

Starting point is 00:13:08 from these customer escalations, and you go through that process and you revise your plan again, and then by the time, usually by the time it's end last week of February, everybody's forgotten the actual plan, right? And now we are executing off of like some other, you know, list somewhere. Right? And so and by the way when you mention this when you mention this at times politely of course you might mention like you know I'm noticing we are not actually like really using the plan that we spend four to six weeks minimum doing and then some smart person in the room Chimes in with plans are useless but planning is everything Okay some I don't know Eisenhower somebody else I don't know

Starting point is 00:13:54 No, who said this? Plans are useless, but planning is everything. Nobody knows what it means. Nobody knows what that means, but everybody appreciates. Ah, plans are useless, but planning is everything. Right? So I went through a few years of this. And then I go, you know what?

Starting point is 00:14:14 I'm going to bend some rules here. And so what I realize, Lenny, is you don't have to go through these four to six weeks. and it was an accident. Basically what happened is around that time, the product I was working on Stripe Connect, that was like it's like a major product for Stripe, major, major business for Stripe. And I had put together a product strategy,

Starting point is 00:14:39 like a real product strategy for this product. And so this must have been like earlier in the year. And so now planning season came along, right? And the interesting thing I found is that because I had a real product strategy, not one of those fake ones, a real product strategy that I had gotten alignment on with everybody. My planning for this major product for Stripe took me like three days. So while a lot of my peers, unfortunately, for their own products were in this like four to

Starting point is 00:15:16 six week cycle of like planning and meeting and blah blah blah, I just put it all together in three days, right? And whatever artifacts were needed, I put them together. I did not fill out some templates. That's where it's about bending the rules, because if a template doesn't make sense, why should I fill it out? Right? Like, there's no need to fill it

Starting point is 00:15:36 out. And so that's when I realized that actually, actually, if you have a real product strategy, a real one that everybody is aligned with, that you have got pre-alignment on, then a lot of this nonsense we tend to do with annual planning actually goes away. Now, you still have to

Starting point is 00:15:52 some resource allocation and all of that. But even there, you don't need that false precision. Like, how many of you have gotten into arguments about, so should it be eight engineers for this team in 2025, or nine engineers for this team in 2025? Like, who cares? We all know that even those numbers that we set up, we don't actually follow through on them, right,

Starting point is 00:16:16 as 25 happens. So that's just an example of where, where we spend a lot of time on things that we think are strategic, that we think are important, but actually we ought to spend that time on other much higher leverage things. Now it does require some upfront work, in this case, upfront work on a clear product strategy that everybody understands, that everybody's aligned on. But frankly, if you have that, planning should be a breeze. So what would be your kind of tactical tip for folks that want to do this better?

Starting point is 00:16:56 I know there's like probably a billion examples of these sorts of things you shared, so planning is an example. Folks that want to be less busy, maybe on that one, is it give yourself very little time and focus on strategy and let that be the plan, basically, versus like every single person in their roadmap for the next six months? Like what's the piece of advice you share there? And then I want to move on to the next question because I want to make sure we get through all these questions. Yes, you know, there's definitely a specific tip which is if you do have a strategy that will make a lot of your prioritization problems go away.

Starting point is 00:17:28 It will make a lot of planning problems go away. And even if you do have some escalation from sales, which you will or from support or somewhere else, you now have at least a more rigorous framework to kind of figure out what to do with that escalation. So there's definitely that. But I think the other thing I want to share is that, and this was my other realization as I asked the question, why am I so busy, is I realized that I am so busy because I'm not making good product decisions.

Starting point is 00:18:05 Okay, now you have to understand by this time I'm like 15 years into building products and whatever, 11 years into being a product manager. And so I think I'm pretty good. Like, that's my kind of sort of self-image. But then, again, if I'm being honest to myself, I'm not making as good product decisions as I can. So can I share an example of that?

Starting point is 00:18:33 So what I noticed is that, you know, you have a meeting about some product feature that somehow is requested or is really important, whatever the case might be. And so you have a meeting with some stakeholders and your engineering team designers, etc. And then you're trying to decide should we build this or not. And, you know, somebody says, you know what, like, why are we making, like, why are we doing a meeting for this? You know, I read somewhere, or I heard Bezos say that two-way doors, you should, like, it's a two-way door.

Starting point is 00:19:13 You quickly make a decision. Like just quickly make a decision and move on. Okay? This is a two-way door. And so you say, yeah, that's right. Like any time we hear something like that, two-way-door, like, oh, that person's really smart. So I want to be like them. So I noticed that myself and my team, we were making these kinds of decisions without actually thinking through, like, very clearly thinking through customer motivation, very clearly thinking through different decisions.

Starting point is 00:19:44 very clearly thinking through a distribution approach for whatever this feature is and You know well it sounds like oh you know of course you should be doing this I guarantee you this is not how most product teams work right like they're talking about well is Bob the engineer going to be free And when are they free and if they are free then let's build the feature right like that's kind of how a lot of product decisions happen and the challenge here with this kind of approach And again, this is what happens in practice. I'm not talking about whatever theory you read. This is what happens in practice.

Starting point is 00:20:20 So when you follow this approach and you assume that, oh, this is a two-way door, we can kind of kill the feature. In reality, it doesn't work out that way. Because here's what happens in reality. So in reality, you commit to the feature, and it's going to take five, six weeks to do it, and then a couple more weeks to make sure to ramp it up, et cetera. right and so now the feature is out right and now you have your Q1 QBR right say

Starting point is 00:20:49 two months from now you have your Q1 QBR right and you're gonna present your business review whatever you're gonna present what you did what did what did you do last quarter how are your ships performing from last quarter and so now it's time to talk about this feature right at the QBR because you have to kind of share that now as you start talking about this feature you know, the CEO will ask, so yeah, we launched the feature, I'm very glad we launched this feature, how is it doing? Right?

Starting point is 00:21:20 And you want to be able to say, you are the PM leader, you want to be able to say something smart and something that makes you look competent, right? But the challenge is the feature hasn't had much adoption. Right? So I'm not going to ask anybody to raise hands, but I think most PMs are familiar with this conundrum, right? And of course we are verbally very agile as product leaders. So what we say is we don't have data, so we use favorable anecdotes. And so we say, yeah, we launched the feature.

Starting point is 00:21:55 And you know what, this customer from this company really loves the feature. And we put in an anecdote, right? It's like life-changing feature. It doesn't matter that they're the only person using it. That doesn't matter. Life-changing feature, right? We use data when it favors us. We use anecdotes when it favors.

Starting point is 00:22:11 So anyway, so we present that. Now we do have the sales counterpart in the room too, our sales counterpart. And they say, you know what, though, we're still not winning many deals because of this feature. And so, of course, the CEO asks, like, so what's up? Like, why aren't we winning deals even though we have the feature? So the people on the customer side usually we respond, well, I'm glad we have the feature, but it's not full featured yet. We need all these other bells and whistles to meet the table.

Starting point is 00:22:41 table stakes, right? So now what happens? Somebody uttered the word meet the table stakes. Now it's over for you. Because now the only response you can give is, oh yeah, that's already part of the plan. And now you put your engineering leader on the spot and you say, Alice, isn't it? Like haven't we allocated engineers to it already? And so now Alice has to come up with some response, which is like, yeah, yeah, yeah, you know, Carol, and David are going to work on it. You know, it's slotted for one of these sprints, right? And so now you exit the QBR, you high five each other, well, good job, team, great job, et cetera, et cetera. But now you have signed up for even more work. For a feature you should not have built in the first place. That's where we're busy, right?

Starting point is 00:23:36 And like through a product leader's life, what happens is we just accumulate all of this data, Right? Like feature after feature. So I guess what I'm saying, Lenny, is one of my other tactical tips would be sometimes it is useful to pause for two minutes or two days or two weeks before making that decision, right? Because frankly, most doors that look like two-way doors are actually one-way doors. They are two-way doors at Dezos' level. But as a PM leader, for you, they are one-way door.

Starting point is 00:24:16 And that's what's making you busy. Wow. I feel like you're a stand-up comedian slash product manager. That was incredible. This episode is brought to you by Vanta. When it comes to ensuring your company has top-notch security practices, things get complicated fast. Now you can assess risk, secure the trust of your customers,

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Starting point is 00:25:19 I know it's Spotify. I heard one of their core values is talk is cheap, but it's the virtue version of that. It's like they actually prefer to talk more, and I think that's exactly what you're saying. Basically spend more time on these things that seemingly seem just like small little ideas that experiments. Yep.

Starting point is 00:25:37 Thinking is cheap, so you should do more thinking, not less. Amazing. Shraos, what's your second question? Yes, so my second question, I have to get the words right. Do I actually have good taste? Do I actually have good taste? Is my second question. Yeah.

Starting point is 00:26:00 And, you know, for me, I asked this question after, again, all of these things. By the way, everything I say, I have been that guy, I've made that mistake, right? So that's why I just have to admit to myself that, yes, I've made these mistakes. And one of the mistakes I made, this was when I was at Google, and I was kind of relatively new to product less, about less than five years. And at Google, there's some parts of Google where you would be told as like a, you know, kind of like an early career PM that, like, we don't do strategy here. Strategy is for MBAs. Okay? We are all about execution.

Starting point is 00:26:46 Okay? So I'm in this environment. I'm naive. And I'm like, I look around me and I'm like, Google is the most successful company on the planet at the time. And they are saying this, and I'm hearing this consistently. So it must be right. It must be right. And so I start saying it.

Starting point is 00:27:08 Right? I start saying, oh, yeah. you know, execution is everything and we don't do strategy around here. And I even remember there were not that many PMs, but there was a PM at Google who was kind of like the same level as me, but he just had much more wisdom than me. And he was trying to nudge me into, like, I was managing a product, and he's like, what is your strategy here?

Starting point is 00:27:31 And I was like, I told him the same thing. Like, oh, no, no, what are you talking strategy? We don't need strategy. We just need to get shit done, right? Like, that was the thing. And so I kept repeating that mantra until I got to Twitter. So this is Twitter right after their IPO. And I saw Twitter had like an incredible asset, which is the product and the network effects.

Starting point is 00:27:56 It had other incredible assets including the brand. It had other assets that were great, including the talent. And yet this company was struggling. Like the product was struggling. And even if it wasn't struggling, it was making it. wasn't struggling, it was making a lot of money, but the point is it was not meeting its potential. So that's when I realized, and it took me, it wasn't like some sudden realization. It took me like six to nine months of being at Twitter.

Starting point is 00:28:20 This is circa 2014. That's when I realized that, oh my gosh, Twitter's biggest problem is a product strategy problem. The reason they are struggling is they don't have a real product strategy. Now, of course, attempts were made to create a product strategy, but it wasn't a real, compelling, cohesive product strategy. So that's when I realized the folly of like, oh, wait a minute, I spent, like, I was at Google six years, I spent like most of those six years kind of saying,

Starting point is 00:28:59 like, ah, strategy is useless, there's no point to strategy, execution is where it's at. I'm like, no, actually, I was wrong. Right? And that got further solidified as I went to Stripe and I was kind of now growing like earlier stage products and kind of trying to make them you know highly highly successful. I saw an even greater kind of value and importance of having a clear strategy. And so that made me realize basically, you know, we talk about taste, right? Like we all talk about taste and it's about the beautiful pixels and the perfect product and the, you know,

Starting point is 00:29:37 whatever else, right, like the Steve Jobsesque passion and all of that, whatever it is. And yes, taste is about that. But I think there is something that we as product leaders, and certainly I did, needed to recognize about taste as just a factor in pretty much everything we do. Right? Which is, like, do we have good taste around the beliefs we choose? to create within ourselves as product leaders, and then those beliefs end up dictating everything we do,

Starting point is 00:30:17 right, including how we manage, how we lead, how we make decisions. And so it's that taste I'm talking about when I say, do I really have good taste? And when I asked myself this question, and again I had to be like, I really had to, to dig deep. It wasn't easy.

Starting point is 00:30:40 But at some point I realized that, no, actually, I don't have good taste. I don't have good taste in how I choose to evaluate things that come my way. Again, not in terms of the product, right? Because by that time, I had skills to say, well, this should not be a two-step flow, this should be a three-step flow, whatever the case may be.

Starting point is 00:31:02 But I still did not have good taste in terms of how I choose what. What are the things I choose to believe? How do I learn? Who do I learn from? What content I learn from? What content I resonate with. And then I went on this journey to kind of like try to develop that better taste.

Starting point is 00:31:21 What I'm hearing is people focused maybe too much on the output, like the experience, user experience design taste versus what they choose to take in as informing their taste. And what they see as an example of great and correct. Is that what you're saying? Yeah. And, you know, look, taste is about the ability to identify what is really good without needing to see its results. Right? Because, look, it requires zero taste right now for anybody to say, oh, that C of Nvidia is a genius.

Starting point is 00:32:16 Right, Jensen is a genius. If you are saying that in 2024, it actually requires zero taste because you can just look up Nvidia stock price. Like, it requires zero skill. But to be able to say that in 2010, you have to realize Jensen Wang didn't change much between 2010 and 2024.

Starting point is 00:32:45 Right? So, like, Lenny, even in sports, right? Like there's this, like, there's this saying game recognized game, right? And that's about taste. But what we need to understand is it's game recognized game before the game is called. Right? Like game recognized game in the practice session. Because it takes no genius right now to say, well, Patrick Mahomes is like, you know, great quarterback, right?

Starting point is 00:33:17 Like, or Virat Kohli is a great cricketer or whatever else, right? Like, it requires no genius to do that. It requires zero taste. So I also believe some of us, like, especially as we get more senior and we get more successful and, you know, we just, like, get a lot more scope and responsibility and a lot of accolades. We become these tough graders, right? Like, I don't like anything, right? Like, ah, this is crap, this is crap, this is crap.

Starting point is 00:33:45 Again, that requires zero taste. Anybody can say that. Anybody can just say everything is horrible, right? So I do think there is something about being able to understand that. And I think there's like, like I'll share some examples, right? Like this two-way door thing. So let me just share a few observations if I might. So like the first one is we get overly excited about cool metaphors.

Starting point is 00:34:13 Okay, like one-way door, two-way doors. Right, there's some guy, I don't know who it is, I just read somewhere. There's some guy who had written a blog post about this, this idea, but he called it reversible and irreversible decisions. Okay, and it was the same idea. And I think somebody was lamenting that that did not catch on, reversible and irreversible decisions. But what caught on is two-way door and one-way door.

Starting point is 00:34:43 What's the difference? The only difference is you got attracted to the catchy metaphor, right? And the other one is the authority bias because Bezos said it. Take another example. We get very, like we get very impressed with alliterations. I'm serious, we get very impressed with alliterations. So how many of us love fail fast? FAL FAST.

Starting point is 00:35:14 Okay, nobody's going to raise hands now. Okay, fine. Maybe you truly don't love fail fast. How about fast follow? How many of you love fast follow? Like, let's consider that, right? Like, fail fast. You're going to fail fast.

Starting point is 00:35:33 What if that thing were called fail quickly? It's the same meaning. Do you think you would be as attracted to that idea if it were called fail fast? quickly? No. Probably not. So what changed? The only thing that changed is one is an illiteration.

Starting point is 00:35:51 Right? So I see this in everything. Like, you know, let's see. You know, the other one is we also get very impressed with complicated charts and math we don't understand. And some of you product leaders who are at the top of the game, you actually use this as a strategy. use this as a strategy. Right? So as I realized that, here's the outcome.

Starting point is 00:36:25 Here's the outcome of kind of asking myself that question was that what I realized is I kind of, you know, everybody says, oh, I'm a first principal's thinker, like, I'm a rigorous thinker, whatever. But I realized that if I really want to be that, I have to shed a lot of these, like, just patterns that were just like, you know, built in me. Right.

Starting point is 00:36:52 And I kind of have to evaluate the idea separate from all of its like social proof and authority proof and whatever else. Right. And that ended up being a meaningful change in my growth as a product leader. because the moment I started shedding these kinds of social proofs and authority proofs and all of that, it just made me a much, we all again think we are critical thinkers, but we are not. So it made me a more critical thinker. I want to move on to the next question, just so we can get through some of these questions. Before I do, can you just show people your notes real quick, just like show it, like from a distance?

Starting point is 00:37:38 This is how Shraos plans for something like this. There's like color coding. Like, I wish I understood what was going on there. This is my, people ask me what's your favorite note-taking app. It's a common question I get. And I say this, right? Like, it's a $5. Like, I guess the pen costs $3.

Starting point is 00:37:57 And I think the Office Depot clipboard costs. Wait, isn't that pen? Does it have the different color clicking? Yes, yes. Yeah. Yeah, exactly. This is great. That's going to be another podcast episode.

Starting point is 00:38:09 Okay, so we want to try to do two more questions. six minutes left. The last one's a bonus. So maybe we touch on it briefly. Shraeus, what's your third question? So my third question is, why does my job feel so frustrating? Why does my job feel so frustrating? And it goes back to the point that like, you know, look, I loved, loved my PM leadership job, right? Like, I just absolutely loved it. And I think looking back, I would not have exchanged it for anything else. any other experience. That said, there were daily frustrations.

Starting point is 00:38:46 There were daily frustrations in that job. And a lot of it has to do with the fact that, you know, the PM leader's job is extremely lonely. The PM's job, the PM's on your team, their job is also lonely, but a PM leader's job is further lonelier. Right? So there's that.

Starting point is 00:39:02 There's also, you know, what I learned at the time when I started asking this question is that, our jobs get frustrating when we behave most of the time in misalignment with our superpowers and who we truly are at our core.

Starting point is 00:39:32 So for me, as I was evaluating that question, why am I getting frustrated every day? I love the job. I love the macro, but I do not like the macro, a micro. And so why is that? And that's when I actually, like, there's

Starting point is 00:39:49 you know, a simple framework that I've shared, which is you can be doing your work at three levels. Product work happens at three levels. There's the impact level. There's the execution level. And there's the optics level. My epiphany, as I was kind of exploring this question, was I have a preferred level at which I like to operate. but if most of the day and most of the week and most of the month I am forcing myself to operate in not my happy place

Starting point is 00:40:26 in my non-deefault level that makes me very frustrated right so so many product leaders their happy place is the execution level you know in my case my happy place is the impact level so that is fine your happy place can be whatever level. It doesn't matter. But the point is, like, as you go higher up in the corporate ladder, no matter what kind of company it is,

Starting point is 00:40:57 you are now going to have to spend a lot of time on optics at the optics level. And I have willpower. I have the skills to do it. I have all of that. So it's not about willpower or skills. But willpower is finite. Right? So as I spent day in and day,

Starting point is 00:41:15 out like just like mostly doing optics work, I realized I was not happy and I was getting frustrated, right? And so that's when I realized the solution, which is I kind of, I have to abandon the traditional path that like, oh, after this level I'm supposed to do this and then I'm supposed to do this and then this is what society expects. This is what my mom expects. This is what, what will people say on LinkedIn when they see my LinkedIn profile? Right? Like, oh, he has this progression, this, and then what, stopped? Why did it stop? Right? So when I realized this, I said, you know, like when a team grew to a certain size, so when I was at Stripe, when I realized this, when the team I was managing it had a fan out of about 50 people, so this includes like engineers and everything, I said, this is enough. Because for me, like, any time a team goes to like 50s and hundreds and beyond,

Starting point is 00:42:10 it is a law of corporations that you're going to have to spend a lot of time at the optics level. So instead of just pushing, pushing through against who I truly am, what did I do? I just went back to more of an earlier stage product. And then I was fine with like, you know what? I'm not going to like, you know, just play the corporate game as an example. So I guess my, you know, my suggestion would be like identify your superpowers.

Starting point is 00:42:41 And you know, like Shakespeare said, like to dine on. own self be true, right? Like just be honest to yourself. Like operate your career and make your career decisions, not out of expectation, not out of envy, like the LinkedIn envy of like, oh, this person is at a different level. We both went to the same grad school. So I got to, no, identify your superpowers because if you identify your superpowers and work in accordance with them, you will do the best work of your life. You will love it. And you will be great at it, and you won't have that frustration. I wish we had an hour for every single one of these questions.

Starting point is 00:43:27 I feel like there's so much more to get into. We have 40 seconds. Do you want to touch on your last question, or do you want to leave that for a follow-up discussion? Let's touch on it. Let's touch on it. We've got to go, though, in 30 seconds. All right. My last question is, am I really listening?

Starting point is 00:43:43 Okay? And this is perhaps the hardest one for me, because I thought, of course, I'm a good listener, because I listen, then I recap, and I make eye contact, and I tell them this is what I heard and all of that nonsense. I realize there is an entirely other level to listening, which once you understand that there's an entirely other level to listening, that is what enables you to be a world-class leader. And so that is what I guess my last takeaway is, like,

Starting point is 00:44:18 ask yourself, am I really listening? If you want resources that are very good. few people who actually talk about what that real listening means. I would refer you to what Rick Rubin says about listening. I would refer you to what Dihawks said about listening and what Drucker said about listening as some pointers. Amazing. Shreyes, you said you were going to hang out for the next hour somewhere?

Starting point is 00:44:40 You want to share that real quick and then we'll get off? Yes, I'll maybe try to hang out in the back part of the room. Be quiet back there too. Yes. Okay. Streyas, thank you so much for being here. Great. Thank you.

Starting point is 00:44:51 Oh, should we take a picture? Oh, yeah. We're going to take a quick selfie. We're going to take a picture. There we go. They're going to turn lights on, I think. Come on in. Okay.

Starting point is 00:45:03 All right, folks. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at Lenny's podcast. com. See you in the next episode.

Lenny's Podcast: Product | Career | Growth - 4 questions Shreyas Doshi wishes he’d asked himself sooner | Former PM leader at Stripe, Twitter, Google

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