4 questions Shreyas Doshi wishes he’d asked himself sooner | Former PM leader at Stripe, Twitter, Google

Summary

Podcast Summary

Title: Lenny's Podcast: Product | Growth | Career
Host: Lenny Rachitsky
Guest: Shreyas Doshi
Episode: 4 Questions Shreyas Doshi Wishes He’d Asked Himself Sooner
Release Date: October 31, 2024

In this insightful episode of Lenny's Podcast: Product | Growth | Career, host Lenny Rachitsky welcomes Shreyas Doshi, a former Product Management (PM) leader at industry giants Stripe, Twitter, and Google. Recorded live at the Lenin Friends Summit in San Francisco before an audience of a thousand, Doshi delves deep into four pivotal questions that shaped his career. These questions not only reflect his personal growth but also offer valuable lessons for current and aspiring product leaders.

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1. Why Am I So Busy?

Timestamp: [05:37]

Shreyas begins by addressing the pervasive issue of busyness among product leaders. He reflects on his 16-17 years in product management, spanning roles at Stripe, Twitter, and Google, where constant busyness led to significant stress and physical manifestations of that stress. Despite implementing various productivity frameworks like the LNO (Listen, Note, Optimize) framework and maintaining meticulous to-do lists and calendars, the root cause of his overwhelming workload remained unaddressed: scope.

Key Insights:

• Scope Inflation: As product managers climb the corporate ladder, their scope naturally expands, leading to increased responsibilities that traditional productivity hacks can’t mitigate.
• Annual Planning Pitfalls: Doshi criticizes the traditional annual planning cycles, which often consume months without delivering lasting strategic value. He recounts his experience at Stripe, where implementing a genuine product strategy drastically reduced planning time from weeks to mere days.
• Strategic Alignment: A clear and aligned product strategy can streamline planning processes, allowing product leaders to focus on high-leverage activities rather than getting bogged down in procedural formalities.

Notable Quote:

“If you have a real product strategy, planning should be a breeze.”
— Shreyas Doshi [09:42]

Tactical Advice:

• Develop a Clear Product Strategy: Invest time upfront to create a well-defined strategy that aligns with organizational goals. This alignment minimizes the need for extensive planning cycles.
• Avoid Template Dependency: Don’t feel obligated to follow rigid planning templates. Customize your planning approach to fit the unique needs of your product and team.

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2. Do I Actually Have Good Taste?

Timestamp: [25:36]

Doshi explores the concept of "taste" in product management, emphasizing that it’s not just about aesthetics or design but also about the underlying beliefs and judgments that shape decision-making processes. He recounts his early career at Google, where the mantra was execution over strategy, leading him to suppress strategic thinking despite its later proven importance.

Key Insights:

• Authority Bias and Alliterations: Doshi highlights how catchy metaphors and authoritative endorsements can bias decision-making. For instance, terms like "two-way doors" or "fail fast" gain traction not necessarily because of their merit but due to their appealing phrasing.
• Critical Thinking: To develop good taste, product managers must overcome social and authority biases, focusing instead on objective evaluation of ideas and strategies.
• Continuous Learning: Building good taste involves deliberate learning from diverse and credible sources, refining one’s ability to discern quality without relying solely on external validations.

Notable Quote:

“Thinking is cheap, so you should do more thinking, not less.”
— Shreyas Doshi [25:41]

Examples Provided:

• Reversible vs. Irreversible Decisions: Doshi criticizes the adoption of the "two-way door" metaphor, suggesting that simpler terms like "reversible decisions" might be equally effective without the catchy alliteration.
• Fail Fast vs. Fail Quickly: He illustrates how alliterative phrases are more appealing but not necessarily more effective, advocating for substance over style in terminology.

Tactical Advice:

• Evaluate Ideas Independently: Strip away the catchy language and assess the core value and applicability of concepts.
• Develop Personal Frameworks: Create and adhere to personal frameworks for decision-making that rely on evidence and critical analysis rather than external influences.

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3. Why Does My Job Feel So Frustrating?

Timestamp: [38:18]

Doshi delves into the emotional challenges of being a PM leader, particularly the frustration that stems from operating outside one’s core strengths or "superpowers." He explains that as product leaders ascend the corporate hierarchy, they often find themselves entrenched in tasks that don’t align with their inherent skills and interests.

Key Insights:

• Alignment with Superpowers: Frustration arises when PM leaders spend disproportionate time on activities that don’t leverage their strengths, such as optics management instead of impactful product strategy.
• Three Levels of Product Work: Doshi categorizes product work into impact, execution, and optics. Effective leaders should aim to operate primarily at their optimal level (e.g., impact) and minimize time spent on secondary levels.
• Career Navigation: Recognizing and prioritizing one's strengths can lead to more fulfilling and less frustrating roles. This might involve refusing to scale beyond optimal team sizes to maintain alignment with personal strengths.

Notable Quote:

“Identify your superpowers and work in accordance with them, and you will do the best work of your life.”
— Shreyas Doshi [43:24]

Tactical Advice:

• Assess Your Core Strengths: Regularly evaluate which level of product work you excel at and enjoy the most.
• Adjust Your Career Path: Don’t feel compelled to follow traditional career progression if it leads you away from your strengths. It’s acceptable to redefine success on your own terms.
• Delegate and Streamline: Where possible, delegate tasks that don’t align with your superpowers to maintain focus on what you do best.

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Bonus Question: Am I Really Listening?

Timestamp: [43:37]

Concluding the episode, Doshi poses a profound question about the depth of listening skills among leaders. He distinguishes between superficial listening—where one merely hears and recaps conversations—and deep, meaningful listening that fosters genuine understanding and effective leadership.

Key Insights:

• Levels of Listening: Effective listening transcends basic acknowledgment and involves fully engaging with and understanding the speaker’s perspectives and needs.
• Leadership Impact: World-class leaders distinguish themselves through their ability to listen deeply, thereby making more informed and empathetic decisions.
• Continuous Improvement: Enhancing listening skills requires intentional practice and a commitment to truly understanding others beyond surface-level interactions.

Notable Quote:

“There is an entirely other level to listening, and that is what enables you to be a world-class leader.”
— Shreyas Doshi [43:38]

Tactical Advice:

• Practice Active Listening: Engage with speakers by asking clarifying questions and reflecting on their points rather than formulating responses prematurely.
• Seek Feedback: Regularly solicit feedback on your listening skills to identify areas for improvement.
• Study Exemplary Leaders: Learn from figures renowned for their listening abilities, such as Rick Rubin and Peter Drucker, to model effective listening behaviors.

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Conclusion

This episode offers a treasure trove of wisdom from Shreyas Doshi, challenging conventional approaches to productivity, strategic planning, personal alignment, and leadership communication. By introspecting on these four critical questions, product leaders can foster greater efficiency, strategic clarity, personal fulfillment, and empathetic leadership within their teams and organizations.

Final Notable Quote:

“Thinking is cheap, so you should do more thinking, not less.”
— Shreyas Doshi [25:41]

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Additional Resources: For listeners seeking to delve deeper into the topics discussed, Doshi references influential thinkers such as Rick Rubin, Dee Hawk, and Peter Drucker for enhancing listening skills and critical thinking.

Connect with Shreyas Doshi: Stay updated with Shreyas’s insights and writings by following his Twitter profile.

Follow Lenny's Podcast: Subscribe to Lenny's Podcast on Apple Podcasts, Spotify, or your favorite podcast app to never miss an episode filled with actionable advice from top product leaders and growth experts.

Transcript

[Lenny Rachitsky]

Today, I am super excited to bring you a very special episode with Shreyas Doshi, recorded live at the Lenin Friends Summit in front of a thousand 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 ask 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 it helps the podcast tremendously. With that, I bring you Shreyas Doshi.

[Lenny]

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

[Shreyas Doshi]

Thanks, Lenny, for having me. This is amazing.

[Lenny]

I was going to ask. We recorded our first episode, I think two years ago, and it was. I was like 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.

[Lenny]

What?

[Shreyas Doshi]

So crazy. Only in sf.

[Lenny]

What kind of car was this? Same old.

[Shreyas Doshi]

It was a Honda CR V. Ok, wow.

[Lenny]

I'm told this venue is also used for Jimi Hendrix performed here and Aretha Franklin performed here. So we're in. It's like Jimi Hendrix, Aretha Franklin, Shreyas.

[Shreyas Doshi]

There we go. That's going up on my Twitter bio soon.

[Lenny]

Okay, so usually when we talk, you're full of ideas and you're full of answers. When we were preparing for this, he told me, I have questions. I have questions I want to ask.

[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 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 had asked myself sooner.

[Lenny]

Awesome. Yeah.

[Lenny Rachitsky]

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[Lenny]

What'S the first question?

[Shreyas Doshi]

Right, so let's see. The 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. 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'd 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, like, the product. I did product work for about 20 years before I started 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.

[Lenny]

Just like health issues that you had.

[Shreyas Doshi]

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 for three days. Doesn't feel good.

[Lenny]

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

[Shreyas Doshi]

That's it.

[Lenny]

Yeah.

[Shreyas Doshi]

Whoa.

[Lenny]

Everyone's like, everybody, yeah. People are 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. You know, 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 tips and techniques, right? Like maintain a to do list. I found the LNO 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, 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. 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 kind of find some answers on sort of how to deal with that scope. Right. And so perhaps we can talk about that. What do you think?

[Lenny]

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 newsletter post 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, right? 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? Right. 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. Right. And so I noticed for instance, that at some point that was making me like 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 you know, there you go, you lost four, five, six weeks. Like does that sound familiar to folks? Like, am I? 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 champion. 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, 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. 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? Like, 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, right? And so now you try to figure out how you're gonna revise resources. You go talk to some dependency team that's going to sort of, you know, support these new features 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 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. Okay, Some, 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. 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, that was like, 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 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, right? So while a lot of my peers, unfortunately for their own products, were in this like four to 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, you know, 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 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 do 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 as 25 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 leveraged 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]

So what would be your kind of tactical tip for folks that want to do this better? 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 and their roadmap for the next six months. Like 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. 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, 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. Okay. Now you have to understand by this time I'm like, you know, 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, please? 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, et cetera. 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. 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, and anytime we hear something like that two way door, like, oh, that person's really smart. Like, 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 differentiation, very clearly thinking through a distribution approach for whatever this feature is. And you know, while 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 what like you, 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 kind of kill the feature, right? 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 Q1QBR, right? Say two months from now you have your Q1QBR, Right? And you're gonna present your business review, whatever, you're gonna 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, right at the qbr, because you had 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? 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, right? 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, 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 us. So, 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 will 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, 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 why we're busy, right? So. And like through a product leader's life, what happens is we just accumulate all of this debt, 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 Bezos level. But as a PM leader for you, they are one way door and that's what's making you busy.

[Lenny]

Wow, I feel like you're a standup comedian slash product manager. That was incredible.

[Lenny Rachitsky]

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[Lenny]

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 than experiments.

[Shreyas Doshi]

Yep. Thinking is cheap, so you should do more thinking, not less.

[Lenny]

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. Yeah. 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 about less than five years. And at Google, there's some parts of Google where you would be told as 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, 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 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, 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. 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. 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 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, 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 most of those six years kind of saying 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 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 whatever else, right? Like 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, 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, 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 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, 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. 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 learn from, what content I resonate with. And then I went on this journey to kind of like try to develop that better taste.

[Lenny]

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?

[Shreyas Doshi]

Yeah. And you know, like 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 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 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, right? So like Lenny, even in sports, right, like there's this, like there's this saying, game recognize game, right? And that's, 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? 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. Again, that requires zero taste. Anybody can say that, right? 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. 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, 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. 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, right? Take another Example, we get very, like, 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? Like, let's consider that, right? 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? No, probably not. So what changed? The only thing that changed is one is an alliteration, right? So I see this in everything. Like, 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, right? So as I realized that here's the outcome. Here's the outcome of asking myself that question was that what I realized is I kind of. Everybody says, oh, I'm a first principles thinker. I think 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 patterns that were just built in me. Right? 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. Right? So it made me a more critical thinker.

[Lenny]

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. This is how Shreyas plans for something like this. There's like color coding. Like, I wish I understood what was going on there.

[Shreyas Doshi]

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. And I think the Office Depot clipboard cost.

[Lenny]

Wait, isn't that pen. Does it have the different color clicky?

[Shreyas Doshi]

Yes, yes. Yeah. The beak. Yeah, exactly.

[Lenny]

This is great. 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 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. 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. 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. 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 macro, a micro. And so why is that? And that's when I actually like. 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 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 in my non default level, that makes me very frustrated, right? 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 like as you go, you know, 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, right? So as I spent day in and day 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 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 and 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 anytime a team goes to like 50s and hundreds and beyond, it is a law of corporations that you're going to have to spend a lot of time at the optics level, right? So instead of just pushing, pushing through against, like, you know, who I truly am, what did I do? I just went back to more of an earlier stage product, right? 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. And like Shakespeare said, to thine own self be true, right? 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 it. 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]

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]

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 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 Dee Hawk said about listening and what Drucker said about listening, as some pointers.

[Lenny]

Amazing. Shreyas, you said you were going to hang out for the next hour or 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.

[Lenny]

Room and be quiet back there too.

[Shreyas Doshi]

Yes.

[Lenny]

Okay. Shreyas, thank you so much for being here.

[Shreyas Doshi]

Great. Thank you. Oh, should we take a picture?

[Lenny]

Oh, yeah, we're going to take a quick selfie.

[Shreyas Doshi]

We're going to take a picture.

[Lenny]

There we go. They're going to turn lights on, I think. 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 [e-mail] See you in the next episode.