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

0:02Today I am super excited to bring you a very special episode with Shreya Skochi, recorded live at the Lenin Friends Summit in front of a thousand people in San Francisco. This is Shreya'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 Shreya was a game to try this. In our conversation, Shreya 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 essential to build good taste, and also why you're probably not listening as well as you should be.

0:37This was so much fun and a huge thank you to Shreya Skochi 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 Shreya's Do -She.

0:58Shreya, thank you so much for being here and welcome to the podcast. Thanks Lenny for having me. This is amazing. I was going to ask what he, 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 this setup of this episode. 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. Why? So crazy. Only NSF. What kind of car was this?

1:40The Honda CRV. Wow. I'm told this venue was also used for Jimmy Hendrix performed here and Arita Franklin performed here. So we're in, it's like Jimmy Hendrix, Arita Franklin, Shreya. There we go. That's going up on my Twitter bio soon. Okay. So, 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. 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.

2:41And 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. Awesome. Yeah. I love that. Okay. This episode is brought to you by WorkOS. If you're building a SaaS app, at some point your customers will start asking for enterprise features like Samo authentication and skin provisioning. That's where WorkOS comes in, making it fast and painless to add enterprise features to your app.

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5:37What'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 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 disalysified. 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 this new chapter of my career.

6:41And I think I only fixed it in the last three or four years of my career as a PM leader. But, you know, 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. 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 for three days doesn't feel good.

7:30Who here is very, very busy and it's just way too busy, raise your hand. Oh, that's it. Yeah, I know. Everyone's like, everybody. Yeah, if you're like, yeah, yeah, I don't have to raise my hand. I'm busy. Yeah.

7:48Okay, keep going. Yeah. And so, 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 tutelist. 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.

8:39And 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 tutelist, 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?

9:22And 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 school. Right? And so perhaps we can talk about that. What do you think? 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're 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.

9:59And so people are always looking for these. I'm curious to hear where you go with this. I've just like 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. 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?

10:41Right. 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 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 lost four, five, six weeks. Like does that sound familiar to folks? Like am I?

11:21Yeah. 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 tutelists 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 say, take up four to six weeks.

12:03Well, 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 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.

12:42And 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 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.

13:19Right. 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, ah, plans are useless, but planning is everything.

14:07Right. 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, 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.

15:10Right. 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.

15:51Now 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, 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 those that time on other much higher leverage things, right.

16:36Now it does require some upfront work. In this case, upfront work on a clear product strategy that everybody understands that everybody is aligned on. Frankly, if you have that, planning should be a breeze. So what would be your kind of tactical tip or folks that want to do this better? I know there's probably a billion examples of these sorts of things you share, 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.

17:13Like 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. 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 realize that I am so busy because I'm not making good product decisions.

18:05Okay. 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? 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.

18:52And 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, in any time we hear something like that two -way door, like, how 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 differentiation, very clearly thinking through a distribution approach for whatever this feature is.

19:51And, 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 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?

20:28In 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, two months from now, you have your Q1 QBR, right? 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 kind of share that.

21:09Now, as you start talking about this feature, you know, the CEO will ask, so, yeah, we, you know, 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, 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?

21:53And 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 are 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're still not winning many deals because of this feature. And so, of course, the CEO asks, like, so, what's up?

22:28Like, why aren't we winning deals, even though we have the feature? So, the people on the customer side usually 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, it's loted for one of these sprints, right?

23:18And 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? 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.

24:10They are two -way doors at day -zos' level. But as a PM leader for you, they are one -way door, and that's what's making you busy. Wow. I feel like you're a stand -up comedian and 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 risks, secure the trust of your customers and automate compliance for SOC 2, ISO 27001, HIPAA, and more with a single platform Vanta. Vanta's market -leading trust management platform helps you continuously monitor compliance alongside reporting and tracking risks.

24:56Plus, you can save hours by completing security questionnaires with Vanta AI. Join thousands of global companies that use Vanta to automate evidence collection, unify risk management, and streamline security reviews. Get $1 ,000 off Vanta when you go to vanta .com slash Lenny. That's v -a -m -t -a .com slash 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 and experiments.

25:37Yep. Thinking is cheap, so you should do more thinking, not less. Amazing. Shreya, 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. And you know, for me, I ask 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 like 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.

26:30And at Google, there's some parts of Google where you would be told as like, 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. Okay. So I'm in this environment. I'm 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 like just had much more wisdom than me.

27:26And he was trying to nudge me into like, I was managing product and he's like, yes, 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?

27:47Like, 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 it. It took me, it wasn't like some sudden realization. It took me like six to nine months of being at Twitter. This is surcared 2014.