The art of product management | Shreyas Doshi (Stripe, Twitter, Google, Yahoo)

Full Interview Transcript

Lenny Rachitsky: Today, I am super excited to bring you a very special episode with Shreyas Doshi, recorded live at the Lenny and Friends Summit in front of 1,000 people in San Francisco. This is Shreyas’ second time on the podcast. His first visit is the third most popular episode of all time of this podcast, and I love that Shreyas was game to try this.

In our conversation, Shreyas shares three questions plus a bonus question that he wished he’d asked himself sooner in his career. We talk about why product leaders are so busy, why the job is so frustrating, why it is so central to build good taste, and also why you’re probably not listening as well as you should be. This was so much fun, 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 Shreyas Doshi. Shreyas, thank you so much for being here, and welcome to the podcast.

Shreyas Doshi: Thanks, Lenny, for having me. This is amazing.

Questions to Ask Yourself Early

Lenny Rachitsky: I was going to ask, we recorded our first episode, I think two years ago, and I was in a tiny room in my house. I don’t know where you were, but it was very not like this. Thoughts on the setup of this episode?

Shreyas Doshi: 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.

First Question: Why Am I So Busy?

Lenny Rachitsky: What?

Shreyas Doshi: So crazy, only in SF.

Limits of Productivity Hacks

Lenny Rachitsky: What kind of car was this? Say more.

Real Product Strategy Over Long Planning

Shreyas Doshi: It was a Honda CR-V.

Practical Advice for Better Planning

Lenny Rachitsky: Okay, wow. I am told this venue was also used for… Jimi Hendrix performed here, and Aretha Franklin performed here. So it’s like Jimi Hendrix, Aretha Franklin, Shreyas.

The Two-Way Door Trap

Shreyas Doshi: There we go, that’s going up on my Twitter bio soon.

Lenny Rachitsky: Okay, so usually, when we talk, you’re 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.”

The Cost of Missing Strategy

Shreyas Doshi: 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, 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 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 share the questions that I wish I’d asked myself sooner.

The Taste of Beliefs

Lenny Rachitsky: Awesome.

Spotting Authentic Taste

Shreyas Doshi: Yeah.

Judgment Hijacked by Rhetoric

Lenny Rachitsky:

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What’s the first question?

Shreyas Doshi: Right, so let’s see, the first question is why am I so busy? Why am I so busy? And the background is that 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 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’d 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, 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.

Philosophy of Pen and Paper Notes

Lenny Rachitsky: It’s like health issues that you had?

Career Frustrations and Superpowers

Shreyas Doshi: Yeah, yeah, minor stuff. I mean, relatively minor stuff, but playing tennis, and you pull your back muscle, and now you are horizontal for three days, doesn’t feel good.

The Art of True Listening

Lenny Rachitsky: Who here is very, very busy, and is just way too busy? Raise your hand.

End of the Show

Shreyas Doshi: That’s it?

Lenny Rachitsky: Yeah, I know.

Shreyas Doshi: Whoa.

Lenny Rachitsky: Everyone’s like [inaudible 00:07:39] everybody. Yeah, people were like, “Yeah, yeah. I don’t have to raise my hand, I’m busy.” Yeah. Okay, keep going.

Shreyas Doshi: Yeah, and so here’s the thing, when we talk about being busy, and managing your time, energy, all of that, I mean, this is a group of senior product people, so you all know that. Take tips and techniques, like maintain a to-do list. I found the LNO framework very useful for me, which I’ve shared before. 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 a scope. 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.

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 3 or 4 years was I able to kind of find some answers on how to deal with that scope. And so perhaps we can talk about that, what do you think?

Lenny Rachitsky: Yeah, 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 are just going to take on more and more work, and they’ll peter out? I’ll say many of my most popular newsletters posts are, “Here’s productivity tricks and tips.” And so people are always looking for these. And I’m curious to hear where you go with this, of just like that is not the answer long term, there’s a different approach?

Shreyas Doshi: 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? Please. Everybody loves annual planning, great. So let’s take annual planning. If you are a high-level manager, leader within a company, what does your month look like? Or in some cases, unfortunately, what do your two or three months look like when you are going through annual planning? It’s all these kind of 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 team to look after and to support, and then I had product decisions to make and various other things, and I’ve gone on some planning retreat or whatever.

And there you go, you last four, five, six, weeks, does that sound familiar to folks? Yeah? Okay, so I noticed that I needed to change that at some point, and 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. 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 this. So that is supposed to take up four to six weeks.

Well, I realized that you don’t have to do that. And so at some point in my time at Stripe, what I realized is the following, we go through a whole all sorts of just rituals around planning for four to six weeks. Then, we emerge and we share our plan with our executives. You know the questions they’re going to ask, like, “If money were no concern, what would you do? 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? The standard stuff. 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. 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 support these new features from these customer escalations. And you go through that process, and you revise your plan again. And then, usually by the time it’s last week of February, everybody’s forgotten the actual plan. And now, we are executing off of some other list somewhere. And by the way, when you mention this at times, politely of course, you might mention like, “You know, I’m noticing we are not actually really using the plan that we spent four to six weeks minimum doing.” And then, some smart person in the room chimes in with, “Plans are useless, but planning is everything.”

I don’t know, Eisenhower, somebody else, I don’t know 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? I’m going to bend some rules here.” And so what I realized, 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, it’s like a major product for Stripe, major, major business for Stripe. And I had put together a product strategy, like a real product strategy for this product.

And so this must have been earlier in the year. And so now, planning season came along. And the interesting 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. Right, so while a lot of my peers, unfortunately, for their own products, were in this four-to-six week cycle of planning, and meeting, and blah, blah, blah, I just put it all together in three days, 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? There’s no need to fill it out. And so that’s when I realized that 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 do some resource allocation and all of that, but even there, you don’t need that false precision. 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, as 2025 happens. So that’s just an example of 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. Right, 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.

Lenny Rachitsky: So what would be your kind of tactical tip for folks that want to do this better? I know there’s 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 every single person and their roadmap for the next six months. What’s the piece of advice you’d 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.

Shreyas Doshi: Yes, 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, 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 figure out what to do with that escalation. So there’s definitely that.

But I think 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. 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. That’s my kind 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?

Lenny Rachitsky: Please.

Shreyas Doshi: So what I noticed is that 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, et cetera. And then, you’re trying to decide, “Should we build this or not?” And somebody says, “You know what? Why are we doing a meeting for this?” I read somewhere or I heard Bezos say that two-way doors, it’s a two-way door. You quickly make a decision. Like, just quickly make a decision and move on. This is a two-way door. And so you say, “Yeah, that’s right.” And any time we hear something like that, two-way door, you’re 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 very clearly thinking through customer motivation, very clearly thinking through differentiation, very clearly thinking through a distribution approach for whatever this feature is. And while it sounds like, “Oh, of course you should be doing this,” I guarantee you this is not how most product teams work. 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.” That’s kind of how a lot of product decisions happen.

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. So when you follow this approach and you assume that, “Oh, this is a two-way door, we can 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, and now you have your Q1 QBR, right? Say two months from now you have your Q1 QBR, and you’re going to present your business review, whatever. You’re going to present what you 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 at the QBR, because you have to share that/ Now as you start talking about this feature, the CEO will ask, “So yeah, we launched the feature. I’m very glad we launched this feature. How is it doing?” 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. But the challenge is the feature hasn’t had much adoption. So I’m not going to ask anybody to raise hands, but I think most PMs are familiar with this conundrum. 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, and you know what? This customer from this company really loves the feature.” And we put in an anecdote, 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 us. 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 are still not winning many deals because of this feature.” And so of course the CEO asks, “So what’s up? 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 stakes.” 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? 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, Carol and David are going to work on it. It’s slotted for one of these sprints.”

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 why we’re busy. And through a product leader’s life, what happens is we just accumulate all of this debt, 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 Bezos’ level, but as a PM leader, for you, they are a one-way door, and that’s making you busy.

Lenny Rachitsky: Wow. I feel like you’re a stand-up comedian/product manager. That was incredible.

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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 small little ideas and experiments.

Shreyas Doshi: Yep, thinking is cheap, so you should do more thinking, not less.

Lenny Rachitsky: Amazing. Shreyas, what’s your second question?

Shreyas Doshi: 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. And 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. So that’s why I just have to admit to myself that, yes, I have made these mistakes. And one of the mistakes I made, this was when I was at Google, and I was relatively new to product, about less than five years. And at Google, there’s some parts of Google where you would be told as an early career PM that like, “We don’t do strategy here. Strategy is for MBAs, okay? We are all about execution, okay?”

So I’m in this environment, I’m naïve, and 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. I start saying, “Oh, yeah, 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, “Shreyas, what is your strategy here?” 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.” 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 an incredible asset, which is the product and the network effects. It had other incredible assets, including the brand. It had other assets that were great, including the talent. And yet, this company was struggling, the product was struggling. And even if 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 wasn’t like some sudden realization, it took me six to nine months of being at Twitter. 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’re 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 was at Google six years. I spent most of those six years saying like, “Ah, strategy’s useless. There’s no point to strategy. Execution is where it’s at. “I’m like, “No, actually, I was wrong.” And that got further solidified as I went to Stripe, and I was kind of now growing earlier stage products and trying to make them highly, highly successful. I saw an even greater value and importance of having a clear strategy. And so that made me realize, basically…

You know, we talk about taste, we all talk about taste, and it’s about the beautiful pixels, and the perfect product, and the whatever else, the Steve Jobs-esque 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, 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, 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 really had to dig deep. It wasn’t easy, 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, 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. But I still did not have good taste in terms of how I choose what are the things I choose to believe, how do I learn, who do I learn from, what content I learned from, what content I resonate with? And then, I went on this journey to try to develop that better taste.

Lenny Rachitsky: What I’m hearing is people focus maybe too much on the output, like the experience, these 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?

Shreyas Doshi: Yeah. And look, taste is about the ability to identify what is really good, without needing to see its results, because, look, it requires zero taste right now for anybody to say, “Oh, that CEO of NVIDIA is a genius, 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. It requires zero skill. But to be able to say that in 2010, you have to realize Jensen Huang didn’t change much between 2010 and 2024. So Lenny, even in sports, there’s this saying, “Game recognize game,” and that’s about taste.

But what we need to understand is it’s game recognize game before the game is called, right? Like, game recognize game in the practice session. Because it takes no genius right now to say, “Well, Patrick Mahomes is great quarterback,” or, “Virat Kohli is a great cricketer,” or whatever else. It requires no genius to do that. It requires zero taste. So I also believe some of us, especially as we get more senior, and we get more successful, and we just get a lot more scope, and responsibility, and a lot of accolades, we become these tough graders. Like, “I don’t like anything,” right? Like, “Ah, this is crap, this is crap, this is crap.” Again, that requires zero taste. Anybody can say that. Anybody can just say, “Everything is horrible.”

So I do think there is something about being able to understand that, and I think I’ll share some examples. This two-way door thing, so let me just share a few observations, if I might. So the first one is we get overly excited about cool metaphors, okay? Like, one-way door, two-way doors. 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 idea, but he called it reversible and irreversible decisions, 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. What’s the difference? The only difference is you got attracted to the catchy metaphor, and the other one is the authority bias, because Bezos said it.

Take another example, we get very impressed with alliterations. I’m serious, we get very impressed with alliterations. Okay, so how many of us love fail fast? Fail fast, 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? Let’s consider that, like fail fast, “We’re going to fail fast.” 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 quickly?

Lenny Rachitsky: No.

Shreyas Doshi: Probably not, so what changed? The only thing that changed is one is an alliteration. So I see this in everything. Like, let’s see, 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. So as I realized that here’s the outcome of that, asking myself that question, was that what I realized is everybody says, “Oh, I’m a first principle thinker. I am a rigorous thinker,” whatever.

But I realized that if I really want to be that, I have to shed a lot of these just patterns that were just built in me, and I kind of have to evaluate the idea separate from all of its social proof, and authority proof, and whatever else. 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, right? So it made me a more critical thinker.

Lenny Rachitsky: 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 from a distance? This is how Shreyas plans for something like this. There’s color coding, I wish I understood what was going on there.

Shreyas Doshi: People ask me, “What’s your favorite note-taking app?” It’s a common question I get, and I say this, right? It’s a $5... Like I guess the pen costs$3, and I think the Office Depot clipboard costs-

Lenny Rachitsky: Wait, doesn’t that pen… Does it have the different color clicky thing?

Shreyas Doshi: Yes, yes, yeah. A [inaudible 00:38:04]. Yeah, exactly. This is great.

Lenny Rachitsky: That’s going to be another podcast episode. Okay, so we want to try to do two more questions. We have six minutes left. The last one’s a bonus, so maybe we touch on it briefly. Shreyas, what’s your third question?

Shreyas Doshi: 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, look, I loved, loved my PM leadership job. 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. There were daily frustrations in that job, and a lot of it has to do with the fact that 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. So there’s that. There’s also 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.

Okay, so for me, as I was evaluating that question, it’s like, “Why am I getting frustrated every day? I love the job, I love the macro, but I do not like the micro. And so why is that?” And that’s when I actually… There’s 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 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, in my non-default level, that makes me very frustrated.

So many product leaders, their happy place is the execution level. 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, as you go higher up in the corporate ladder, no matter what kind of company it is, 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. So as I spent day in and day out, just mostly doing optics work, I realized I was not happy and I was getting frustrated. And so that’s when I realized the solution, which is 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. What will people say on LinkedIn when they see my LinkedIn profile?” Like, “Oh, he has this progression, this, and then what stopped? Why did it stop?”

So when I realized this, I said, when a team grew to a certain size, so when I was at Stripe and I realized this, when the team I was managing, it had a fan out of about 50 people, so this includes engineers and everything, I said, “This is enough.” Because for me, any time a team goes to like 50s, and 100s, and beyond, 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 just play the corporate game,” as an example.

So I guess my suggestion would be identify your superpowers, and like Shakespeare said, “To thine own self be true.” Just be honest to yourself. 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…” 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.

Lenny Rachitsky: I wish we had an hour for every single one of these questions, 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?

Shreyas Doshi: Let’s touch on it, let’s touch on it.

Lenny Rachitsky: Okay, we got to go though in 30 seconds.

Shreyas Doshi: All right. My last question is am I really listening? 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 realized 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, is ask yourself, “Am I really listening?” If you want resources, there are very 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 [inaudible 00:44:30] said about listening, and what Drucker said about listening as some pointers.

Lenny Rachitsky: Amazing. Shreyas, you said you were going to hang out for the next hour somewhere. You want to share that real quick, and then we’ll get off?

Shreyas Doshi: Yes, I will maybe try to hang out in the back part of the room.

Lenny Rachitsky: Be quiet back there, too.

Shreyas Doshi: Yes.

Lenny Rachitsky: Shreyas, thank you so much for being here.

Shreyas Doshi: Great, thank you. Oh, should we take a picture?

Lenny Rachitsky: Oh, yeah. We’re going to take a quick selfie.

Shreyas Doshi: We’re going to take a picture.

Lenny Rachitsky: There we go. They’re going to turn lights on, I think.

Shreyas Doshi: Oh.

Lenny Rachitsky: Okay.

Shreyas Doshi: All right, folks.

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

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