Jackie Bavaro on getting better at product strategy, what exactly is strategy, PM pitfalls to avoid, advancing your career, getting into management, and much more

If you're a PM, you've almost surely read and been influenced by Jackie Bavaro. And if you haven't, you're in for a treat. Jackie is behind two of the most important books in the PM canon: Cracking the PM Interview and Cracking the PM Career. And she's also one of the smartest people I know on the essential skill of product strategy. In our chat, we go deep into all the ways that you can become better at developing your own product strategy, including what is strategy, what makes a good and bad strategy, on how to very tactically put together a strategy. We also chat about what she's learned going from the first PM at Asana to head of product at Asana, plus a ton of tactical advice on getting to senior PM and then to manager of PMs. A big thank you to Jackie for sharing her wisdom with us. This episode is brought to you by Flatfile. Think the last time you imported a spreadsheet, did it work the first time? Chances are it did not. You probably got some weird error and had to try a bunch of things like removing the blank title rows above your column headers or Googling how to save with UTF-8 encoding. What even is UTF? Who cares? You're just trying to get your file where it needs to go so you can do your actual job. Your customers run into the same issues when it matters most, right after signing up for your product. Enter Flat File. Flat File is the data onboarding platform built to take the acute pain out of importing customer data into your product so they can see the magic that you promised them. Flat File is SOC Type 1 and 2 certified, GDPR compliant, and even HIPAA compliant, ensuring your customers, no matter where in the world they're located, are sharing their data securely and in compliance every step of the way. No more emailing files back and forth. No more help articles that just don't land. Just clean data on day one, when it matters most. Get started importing millions of rows of customer data in minutes at flatfile.com/lenny. This episode is brought to you by Amplitude, the number one product analytics solution. Amplitude helps product teams grow teams, marketing and data teams build winning products faster and turn products into revenue. Amplitude has everything you need including an integrated CDP, self-service analytics, and even an experimentation platform to help you better understand your users, drive conversions, and increase engagement, growth, and revenue. Amplitude is built for teams that want to learn as fast as they ship and ship as fast as they learn. Ditch your vanity metrics, trust your data, work smarter and grow your business with over 1700 customers like Atlassian, Instacart and HBO. Amplitude is helping companies build better products. Try Amplitude for free. Visit amplitude.com to get started.

Jackie, I am so excited that we are chatting again. We've done a bunch of fireside chats over the years in various events and you've always been really generous with your time. And so I just want to say thank you for joining me and I'm really excited to chat again.

Yeah, I'm so excited to chat with you. I'm so excited that you're doing a podcast and I'm glad I get to.

Be one of the early people on it. Absolutely, it's my honor. Okay, so you're kind of a famous PM in the world of product management. You wrote Cracking the PM Interview, Cracking the PM Career, both of which I own and love, and fun fact, my sister was just interviewing as a PM and she used your book and found it really helpful. So thank you for that. Awesome. Yeah. And then also you've written a bunch of classic PM posts on Medium that I reference often and share with people. And also you were the first PM at Asana, ended up being the head of product management at Asana. And that's actually where I'd love to start. Could you just kind of share how you got into product very early on and then how you worked your way up to the head of product management at Asana?

Yeah. So I was just really lucky in finding product management is I went to Cornell, studied computer science and economics. and I'd never heard of the job. And one of my friends who'd been a PM intern the summer before was like, Jackie, you have to apply for this internship. And I said, I'm like a sophomore, I can't be a manager. And they're like, no, you manage the product, not the people, and like, just go apply. So I applied having no idea at all what the job was, and through the interviews I tried to figure it out. And I loved the interview questions. I thought they were a lot of fun. And got the job, became an intern on Microsoft SharePoint services, and stayed with the team, loved that team, went there full time. When I moved to New York, then I started thinking about changing companies. so Microsoft didn't have any product management in New York, so I applied to Google. And I was like, yes, I'm a good product manager. I'm sure I'll get this job. And I got rejected. And I was shocked. I really had thought that I would pass the interview. So a year later, I applied again, and that's when I got into the Google APM program. And of course, at the time, I thought this was like one of the biggest mistakes in my whole career. But looking back, it certainly is what kind of gave me the impetus to write these books and say, like, you know what? Even good PMs, Don't know how to answer these questions. There's a lot we can do to help. And beyond that also then when I joined Google, I very quickly got sent into being an interviewer. And immediately I noticed there was this real difference in how people would answer the questions. And some people like didn't seem to understand what the question was trying to get at. And some people sounded really good because they'd say, well, I'll tell you three things, you know, number one, number two, number three. And then when I paid attention to my notes, I'd be like, wait, they their three ideas weren't actually good ideas, they just sounded like they knew what they were doing. So those really drove me to wanna like share more about how to do well in these interviews. And at the same time, I constantly had people saying, you know, Jackie, my friend's applying to Google, can you talk to them? And I was like, sure, of course, I'll like tell them what we're looking for and I'll like help them understand the interview process. And after doing this like three times, I was like, wait a second, if it's only like my friends of a friend who like are people who work at Stanford and are already very privileged, and I'm telling them how to pass these interviews, like that's not fair. If I'm willing to tell it to a friend of a friend, to be willing to put that out on the internet and share that with everyone because we really want to level the playing field and we don't want to make things more unfair. So while I was at Google, one day I get an email from a friend from an engineer I'd worked with at Microsoft and he's like, Hey, you want to grab coffee? And I was like, oh, cool, sure, I'll be friendly. And at the time, I did not realize that that's how all these recruiting chats start. So I honestly did not realize that this was like, I'm being recruited. I thought it was like, let's just catch up. But I said yes, and then he told me about this company. He's like, Hey, it's kind of like, imagine if SharePoint was really fast. and I was like, oh, like I loved SharePoint and I would love to work on a fast version of that. And that's how I ended up moving.

Over and becoming the first product manager at Asana. There's so many things I want to pull on in what you just shared there. On the book, one interesting point you made is that you kind of wrote the book because it was something you were struggling with and then you saw a lot of other people struggling with it. And I find that that's often the case when you look at books people have written or posts they've written, it's just like, oh, I had this question.

And this was a way for me to get better at it by forcing myself to write about it. Is that basically what happened? Yeah, I kind of had this belief that almost anybody can learn anything. People have different interests, not everybody wants to learn everything. But I find that if you're having trouble learning something, it's just because something's not clicking. There's just something that you're misunderstanding or that other people see that you're not seeing. And if people could just describe it in the way that matched your mental model, then you could learn it. So that's kind of how I feel about this interviewing, is that the reason that some people don't do as well as they could on interviews is just because, like, a lot of these interview questions are kind of like trick questions. When they say like, oh, how would you design a bathroom? I used to think that meant like, what do you want in a bathroom? And that's not what it means at all. It means like, who is the best customer for a bathroom? And what would they want?

But if you haven't been trained in this, you wouldn't know. We're definitely going to talk about interviewing and career and kind of come back to these topics. But going back to Asana, you look at this journey that you took and it sounds amazing and went great. And someone that's kind of starting out, they may feel like, man, how am I ever going to not make any mistakes along my journey and get to a place like Jackie? ended up. And so a question is just, is there like a mistake or some wrong turn you took along this journey that you can share?

Yeah, I'm sure I've made lots of mistakes. One of the ones that comes to mind is that in probably my first or second year at Asana, I very much saw the PM's role is like a person who wants to say no to everybody. I was like, all these people want us to do stuff and we would do way too much and we would like never get anything important done if we just said yes to them. So I need to say no to people. And I kind of got into this defensive mindset and sometimes people would come to me with ideas and I'd be like, are you telling me I can't do my job? job right and like I would just try to say no to them as efficiently and effectively as possible. And I did this one day to my boss and he had some idea for design that I thought was a bad idea. And I was just like, no, we're not gonna do that. And he's like, Jackie, you have to stop shutting me down. And I was like, I'm about to get fired. Like I was like, oh, I have really, really messed up here. And like it definitely like made an impression on me and I was lucky enough to have a coach at the time. So I went to her to talk to her. and really started to rethink how I saw the role, like this like urgency that I felt of like, I need to shut people down as fast as possible to save time as opposed to like, take the time to consider that other people probably have good ideas. And even if their solution isn't what I think is going to be the absolute best solution, the problem they're talking about is probably real. And I can interpret their solution as a way of sharing the problem and like exploring and brainstorming around that. and so it wasn't an immediate change, but I remember at one point she challenged me to like for the next two weeks say yes to everything. And I was like, I can't do that, I wouldn't be doing my job. And she's like, I think you can find a way to do your job and still say yes to people, right? And so you can say like, yes, I agree that is a real problem. Like, yes, I think we could test this design with users and just see what's different with two weeks of saying yes to people instead of no. And I realized that this like protectiveness and like lockdownness that I had Really wasn't something I needed and wasn't something that was serving me because it meant that I couldn't have real collaboration with.

The other people around me. Wow, I love that story. A little thread I want to pull on there. Two questions. How far into your time at Asana did this happen? Because it's surprising how often things like that come up really late in a career and you're like, oh shit, this kind of fundamental thing that I imagined isn't maybe as true as I thought.

In changing course there. So it gets, so maybe let me ask that question just like how, how far into your career was that? This was probably pretty early. I'm like imagining what room it was.

In and I'm like, okay, I know what I time I was, it was definitely in the first maybe six months in. Okay, okay, cool. And then, okay, so you have this coach. What kind of impact have you seen from just having a coach? Something that a lot of PMs ask me about is just like, should I get a coach? How do I find a coach?

I guess just roughly your experience been with a coach and then any advice for folks thinking about getting a coach? Yeah, so there's sort of two different models I've seen people. Some people like to have a coach all the time and that's a person that they can go to and they can explore their ideas and their feelings and how they're like just bounce ideas off of all the time. Have this person who isn't in any way related to like gonna be the person who evaluates them later on so they can be totally honest with them. For me, I find it's better to have a coach when I have a specific thing I wanna work on. I tend to be a little bit like results oriented, action oriented, and I don't like to like just show up and be like, so what are we talking about today? Or like make something up. So I talked to this coach to sort of deal with this issue of like how do I not shut people down and how do I still be a good PM if I'm not saying no to people all the time? But I did, and I worked with her for several months But then once that was gone, then I did start to find that personally, I would make things bigger when I had a coach because I had something that I knew how to solve on my own and I'd like bring it to the coach. And then all of a sudden it felt like it was a big deal rather than a little deal. So I've gone in and out of.

Coaching, but I do it when I have a thing that I want to work on. So going back to Asana, you were there for eight years about what kept.

You there for that long? And then how did you know that it was time to move on? Yeah. So I loved working at Asana and Asana, I think today is incredibly successful, but it was not always obvious that it was going to be incredibly successful. We had some lulls in there. There was a time when we were updating our entire engineering framework from an old version to a new version, and we had like a literal 50% of our engineers working on this. So no new features. We set aside half of our engineers to work on new features, and the other half was just working on updating this framework, which meant that we felt like we were moving at half speed. Like it felt like we were moving really slowly. Customers hated how slow the app was, and this framework change was needed to change that, but we really were not sure that the company was going to be successful. So staying with the company through those days, it really was this feeling that I was getting good growth opportunities, even if the company itself didn't succeed. One of the things I think was really important for me in my career at Asana and growing into head of product management is at one point in my career, my manager, one of the co-founders had a meeting with the two co-founders and planning committee. So the planning committee was like the two co-founders, the head of engineering and the head of business. and they would meet. And after these meetings he would come back to me, my boss, and he'd tell me like, okay, here's the direction we have, here's what you're gonna need to do. And I'd like ask some questions and I'd be like, but what about this? And what about this? And so after a little bit of time, I would start to be like, hey, you have your planning committee today, right? Like here are the three questions I want you to go in and get answered at that committee. And I want you to like, if they say this, I want you to like ask this and this. And after a little bit of that, I was like, it might be easier if I just go. I might be able to save you some time and some energy if I just join you. And it was a way that I sort of talked myself into this higher level meeting, framing it as something that was gonna help out my boss. And it did. It wasn't dishonest, but it was a pretty effective way of advocating to get into this meeting. And so I think once I was in the planning committee, I just got a real front row seat to understand how a company is built and what kind of decisions are happening and what goes on beyond the realm, the narrow perspective of like building features. Right, so going from features to like strategy, but also understanding business strategy and like how do the product choices we make impact our financial plans and whether or not marketing has to hire people and whether or not that means we need to open an office. So I really felt like I was getting a lot of personal growth and I was getting an opportunity to learn things that I wouldn't have that opportunity anywhere else. Because of my sort of background and my deep like knowledge of this product that I was able to be exposed to this and have these responsibilities. So for me, I really felt like I was learning and I was growing and I like didn't know it all yet. And so that's really kept me there for a long time. And then I'd say getting closer to the end of that time, I started, you know, I'd become a manager, I had teams, I'd become a manager of managers, and I was definitely starting to get burned out. It's really, really tough being a manager. As a manager, like one of the ways that I'd always worked as a product manager is a lot of transparency and authenticity, right? A lot of like explaining to people what our goals are and then kind of showing like this is the solution I think will hit our goals, but I'm open to other solutions. As a manager, there are times when my goal is like backfill for someone I know is quitting in a few weeks, but I can't tell anyone about it, right? Or like, you know, there are all these sort of like personal secrets that you have to keep for people as a manager. And there are times where like what the person on my team wants is a promotion to make more money. They haven't necessarily earned it yet. It's not necessarily the right thing to do from a company perspective. So those places where you're sort of torn between these two goals or where like what I want isn't always like perfectly aligned with what's best for the people that report to me, that weighed a lot on me. That was very heavy. And so I was like kind of like, okay, maybe I could use the break. But for a while I kind of felt like, okay, but I don't want to like just leave the company and like things will be in bad shape. So we worked on hiring lots of really, really stellar people, just really talented people and growing people in their roles. And got to a point where I was like, I was like, Everybody's doing great! They don't need me! They can do fine without me! And I thought about like, well, if I left, I just felt this surge of energy thinking like, yeah, if I left that, I'd be excited for what's next. And then started to have this idea of writing the book on careers.

And so that's how I knew it was time to leave. It was also eight years, so it makes a lot of sense that eventually it gets tiring. And then I love the glimpse you shared into kind of the downsides. of being a leader in product. Is there anything more you can add there? Just like people want to be the head of everything and then they get there and they're like, shit, this isn't what I wanted to be doing.

Definitely. So two directions I'll take. One is just like, yeah, that being a manager is not as much fun as being an IC. It's a lonely job. When your team goes out for drinks, they treat you differently when you're the manager than when you're one of the other ICs. So it really is, It's more painful and less fun. So for all these reasons, like you might not want to be a manager. At the same time, I felt like, I'm like, well, what could I have told, you know, younger Jackie to be like, maybe you don't want to be a manager? And there's nothing. There's like nothing you could have told me that would have convinced me not to be a manager. So I might say that if you want to try it, consider it a two-way door, consider it something that you can try for a while. And if you don't like it, a lot of people are now playing with going back to IC. And also to understand the career paths. so when I started as a product manager, I had no idea what salaries people made, none at all. And I knew I wanted to like be able to like support a family and stuff when I grew up. So I kind of assumed that I needed to make it to junior VP level to like be able to do that. And I just had no idea of what salaries were like. And since then I've looked at like levels.fyi is one of my favorite sites. They'll show you salaries at different levels at different companies. And if you make it to like senior PM, which is like one of the middle levels, right? Like this middle senior PM level, at like most of these big companies, you're making as much as a doctor makes. You're making as much as a lawyer makes. You're like making a lot of money. So you don't necessarily need to like climb that career ladder forever to make a lot of money. And especially like at a company like Google, you know, there's a few companies that are known for being like the highest paying companies. You can make a lot of money, much more than you can make at a lot of startups just by being an IC path, just by continuing to do that job. And companies really need people to do that. So I think understanding that there's different ways to grow your impact and grow your career, other than getting promoted to people management. And for me, I think switching companies is one of the really obvious ways is that, or teams of there's one kind of impact you're having at your current job, and maybe you could work on a product that affects more people or has a bigger impact on the people that use it, or something that has more of a social impact type work, but just really thinking about different ways to grow your impact so that you don't make a blind choice towards people management because it seems like it's.

The only way to grow. Along those lines, I know a lot of companies in theory have these kind of icy career tracks. And I find that it's really rare that they end up being really successful and very few people end up going down to them. Is that kind of what you see too, or is there like, I don't know, is there a way to actually be really successful going down that path?

Yeah, so I think that to the extent that you want to be seeing promotions as like you want your level number to go up, I think that it is pretty rare. I think that there's not that many companies that have principal PMs and the ones that have a bunch usually have a partner PM role above that. That's the real principal PM at other companies. And the reason for that is that the reason a company would give you that high of a title is because they have a business need for PM who can have as much impact as like a director, but with a team that's small enough that they can PM the whole team. And there's only a few problems out there like that. So platform type teams can fill that role a lot of the time. Partnerships, somebody who's working on a partnership between two major companies can often fit that kind of description. But there just aren't that many. It's a lot easier to have a big impact if you have, if you're a manager of managers and you kind of can add up the impact of all the people on your teams. So yes, I agree that there's not that many opportunities to go from senior PM to yeah, principal PM to partner PM. I don't think you need to. I think that if you want to pursue the IC path, which I think is a great path, I think thinking of ways to grow beyond the official promotion. So a lot of companies, you can make a lot of money without getting that promotion title. If you're working at a small company, if you're working at one of the companies that isn't the highest paying company, you'll make a lot more money by switching companies than you will by getting promoted at your current company. And like I was saying before, with the thinking about the kind of impact your work has, do you want to work on something that's more cutting edge? Do you want to work on something that your product, that your friends use? Do you want to work on something that's going to save the environment? All of these things, I think, are ways to grow.

They are a career path.

They're just not the like climbing the career ladder. this episode is brought to you by PostHog. PostHog offers a suite of product analysis tools, including funnels, heat maps, session recording, and experimentation, all in one easy to use platform. PostHog is open source, so you can host it on your own infrastructure, which means that you have control over who has access to your data and makes regulatory compliance a breeze because you don't need to send user info to third parties. PostHog's app system works seamlessly with your data warehouse both for importing and exporting data, which enables you to bring your data into one place and easily understand user behavior across a range of touch points. If you'd like to learn more, check them out at posthog.com/lenny.

That's a really important insight that you can keep growing one as a human and maybe even be happier going down one of these other paths, non-manager path, and maybe you don't get the promotions, but maybe you make just as much money as you go the other path. In theory, it's a lot more interesting. And then the other point that you made is really great that if you want to go down that route, it's probably going to be like an infrastructure team or like a new business unit, unlike it to be a user facing piece, because they probably want to build large teams there. A lot of layers. Interesting. Great stuff. Okay. So I want to transition to strategy. You've written a lot about strategy. I share your pieces often with folks. And so kind of diving into that a little bit. First of all, just like, how do you describe what strategy even is? It's like this term that everyone uses.

All the time and they're like, oh, I'm working on strategy. I'm going to get good at strategy. What is strategy in your mind? Yeah, when I worked at Google, one of the promotions I went up for I did not get, and I got the feedback that I needed to be more strategic. And so I was like, okay, great, what does being more strategic mean? And nobody could tell me. And they were like, I was like, well, who's more strategic? And they were like, oh, this person used to be really strategic before she became a manager, but now she does just does managerial stuff. And I was like, okay, I have no role models, no words, nothing to explain what strategy, what it means to be more strategic.

So quick shout out to my book, because I've got like a whole list.

Of what it means to be more strategic. So if you pick that up, you can we can read through that.

Can we find that on Amazon?

Where do you find that book? Yes. This is the Cracking the PM Career. That's on Amazon.

Great.

And it's in the strategy chapter. Great. So what I did is I wrote a document and I called it like on the local universal team. So I called it local universal strategy. And I can't remember what I put in this document. I put it in like just like a random, like what my plan was. But I was like, once I wrote it down and shared it with people, then I started getting feedback on it. And then I could start to like I feel my way to what people meant this strategy. So then I get to Asana and I work really closely with JR, head of product, and I'm starting to get a view of what strategy means. And he's got a robust vision for the product. So, you know, we talked about this idea that when you're playing guitar, your left and your right hand know how to work together to play the guitar. And like, wouldn't it be amazing if at a company, all the teams sort of had that ambient awareness of what other teams were doing together so that we worked seamlessly together and Hasan was the team brain helping this happen. So imagine a world where you didn't have to have these endless status updates and all this work about work because the teams knew what each other was doing and that as you kept track of your own tasks that updated the centralized system that was always up to date. So we had this vision of what the future could be like and we had our strategy which kind of got into this team brain and what does a good team brain have? Well, it has to always be with you so we need to have good mobile and good security. We need to know about the different kinds of work that exist. So we need to like, right now Asana understands this kind of work, we need to add this kind of work. And it has to help you draw insightful connections with the work that it knows. So if we know that you have all these tasks with due dates, we need to be able to let you know that maybe you have too many due dates on next Friday. So I started to build up this idea of strategy. And I was like, okay, I think I've got what strategy is. And a few years later, we hire Alex Hood, our new head of product, and he's like, can you create a strategy for the platform team? And I was like, great, here We have it. And he's like, that's not a strategy. And I was like, what?

I was like, I've been going all.

These years thinking I knew what strategy was, and now I get again find out that I don't know it. And so we had a lot of conversations and kind of figuring out like, well, what's missing? And through all of this, I basically realized that there's three key components to strategy. And not everybody's thinking of all three, but if you have all three, you'll have something that counts as a strategy for anyone you talk to. So three parts of strategy. are your vision. So this is your inspiring picture of what the future looks like. And this is like, Hey, everybody, this is where we want to get to. Don't you want to like, come join me, come build this future with me? Won't this be exciting? And then you've got your strategic framework. So this is where you're saying, here is the market we're going after. Here's what success looks like. And here are our big bets on what we think it takes to win that market. And so that's where you get your pillars, and it's your unique way of breaking down the problem to understand like who you're going after and what it takes to win them. And then the third part is the roadmap. And so this is where you sort of work backwards from your vision. So you say like, okay, I think as a company we can achieve our vision in five years or 10 years or two years or whatever it is. And you say working backwards from that, if we're going to be at our vision in five years, what does that mean we're doing in the intermediate years? I misunderstood roadmap for the longest time. A roadmap in strategy is not a Commitment. Instead, it's a way to double check if your plan makes any sense at all and is even anywhere near feasible. Because what happens to every team I see do these roadmaps, you put it together and you realize we're not going to hit our vision in five years or 10. This is like a 30 year vision if we keep going at the pace we're going. And so it's this wake up call to say, oh, okay, if we want to hit this vision in five years, we need to start working on that big thing now. We need to like take much bigger swings at the bat, we need to say no to a lot more of this optional work. Maybe we need to hire a team that's twice as big. It gives you a way to say that like, probably your strategy did not actually fit into the timeframe that you wanted. And that roadmap helps you see like, okay, what it would it take? And then that can be a little bit of an organizing factor for people across the company to understand like, okay, we're having a major launch in two years, then we need to make sure that we're gonna have the marketing Support we need for that launch, or we might need to have an entirely different business model in two years. We need to do a fundraising round now. So it really helps kind of pull the pieces together.

Wow. It's so actionable and easy to understand. I've never heard it described so simply. Along those lines, say someone creates a strategy. What are signs that it's a good strategy versus like a me strategy?

What should they be looking at? And so I'm probably going to write something on this soon. In the past month, I've actually talked to two totally different people who came to me with the same problem and they said, My CEO brought me a strategy and the strategy is like increase revenue by, you know, 50%. It's a revenue target number. That doesn't seem like a strategy to me. I don't know what to do. And so talking to people, I started to get a deeper sense of what the confusion and the mismatches here. And so I think a good strategy is all about connecting the dots, connecting the dots from this high level business goal of like, we want to increase revenue by this much. to like, this is the feature we're going to do. And it might have many, many dots in between to help get people from one to the other of like, why, given that this is our big picture of you, what we're doing, what's the next step and what's the next step and what's the next step? And as product managers, if you're given a numerical target, that is not a complete strategy. But it's your job now as a product manager to take all of the great product work you've been doing. So let's say you've been doing lots of customer research and you're getting really deep into what the customer pains are and what their needs are. It's your job to take the things you've got now in your mind, you've got a list of like maybe 20 different things your product team could work on. So it's your job to take those things you want to work on and the reasons why you think they're important and match them up against what that larger strategy, that larger financial target was or whatever strategy or vision you're getting from the executives and basically see which of these feature work, which of this product work that I want to do best matches up with those goals and why. and there's probably a few more missing dots in there. You're like, well, I think that this is going to make us the most money, but why is it because I think this will make us most money because it's helping us get more money from our current users. And we think it's going to be really hard to win new users because we're already pretty saturated in the market. Right? That's where you start to get into strategy, that level of detail. And then you say, okay, given that we think it's more strategic to get more money from our current users, here's one thing we can do. What are other things we could do? and how do those stack up against each other? Or maybe it should be that 50% of our effort is on getting more money from our current users and 50% is from going into new markets. Well, which new markets do we think are most promising and what would it take to win those new markets? So I think it's that connecting the dots and the only way you find out what dots are missing is by talking to people and communicating your strategy and communicating it again and again and really listening for people's confusion because people will try to hide their confusion. They won't get your strategy. There's going to be some assumption that you're making that they are not making. And so you have to like pay really, really close attention to find those missing assumptions so that you can then explain like why this connects to this.

That's really good advice of just like looking for confusion and that points out where your strategy is, is lacking. How could PMs get better at strategy at doing this and getting better at this?

Do you have any advice for that? Yeah. So strategy really should be collaborative work. I think that there is some amount to which the PM should go off by themselves and think about what strategy they want and have that in their back pocket because that way you actually can contribute to the conversation. But real strategies should be very collaborative and I think the best way to learn and improve your strategy, one of them is going to be working with the other stakeholders and listening to their feedback and understanding what do they agree with or not agree with. So sometimes it's as easy as a and I can't remember the details here, but there was one conversation on pricing models that we were talking about, and we were each going to go around the room and talk about like, which of the five pricing models did we think was best? And I think I was like number three, as most was like number two. And then our CEO gets, and he's like, I think really number four is the only reasonable one for these reasons. And I was just like, I agree. I've changed my mind. Like, you're right. I just saw it in a way that I hadn't seen. And so just like hearing that, like this accumulation of experiences I think matters so much for so many, for strategy, for data analysis, all of these things where like, like I'm really, really good at data analysis, but only because I've seen so many experiments that I, when I see a set of results, I like can just instantly remember like four similar experiments and like what the conclusion was and what went wrong with it. And so I'll be like, oh yes, this metric is up, but if you check this metric, you can see it's down, which means that it might be this conclusion. So it's just, it's talking to people, listening to them, that builds it up a lot. But that's one half of it, because you can't always just learn something by like a bunch of leaders sitting in a room talking to each other. So I think seeing things through to a certain amount of time really does help. And I think sticking with the team for long enough to be able to measure the results of what you did and ideally like iterate, like being one that's on it for eight years, I got to try something and then try something different and then try something different. And I got to really notice the patterns and test what works and what didn't and form those conclusions. So I think that sticking around long enough to see your results and especially try something else different and see those results, I think can make a big difference.

So what I'm hearing is you get better one doing it over and over and over to kind of being in the conversations and learning from people directly. Is there anything else that like someone that, I don't know, doesn't have a lot of these experiences yet and is like in the room? for these sorts of things that they could maybe study up on or practice just kind of like outside of this to get a little bit stronger in strategy.

Yeah, so definitely there's a lot of cross applying of strategy that I think really is helpful. So one of the great ways to learn strategy is to cross apply strategy from other places. So one of the people I interviewed for my book was Shashir Mahotra, who's CEO of Coda, and he used to work at YouTube. And while he was at YouTube, he had a very big strategic question that the team had to decide about whether if you search for a video that is not on YouTube but is somewhere else like Hulu, should you link them out to that? And the team was having a lot of trouble making any progress on that. But one day he went to a product review for Google Shopping, totally different product, right? Shopping versus videos. But they were having a similar issue and they talked about this idea of consistency versus comprehensiveness. They said, is our product the kind of product where it's better to have consistent results all the time? Like every time you click on a result, it takes you to a Google shopping result? Or is it better to have comprehensiveness where even though the experience will be different each time, we give you a result every time? And so that framing he was able to take from shopping over to YouTube and ask that same question. And the answer didn't have to be the same, but it gave them a new way of looking at the strategy that he was able to use. So I think having that broad view and looking at lots of other products and seeing how they make their choices and like how do they frame their decisions, that's a good way to improve its strategy.

That's a really good reminder of Eigenquestions as a framework. I think if you Google Eigenquestions, you can find it and I'll try to link it to it in this podcast. And Shashir has a lot of great stuff that he's put out there. So good, good call out. Let me ask one more quick question on strategy and then I want to move on to career stuff. So how long should people, I guess early PMs maybe spend time? How much time should they spend on strategy kind of development? And then when does it make sense to start investing in that?

Yeah. So I think that for your first six months on a product, probably don't worry about strategy. For your six months, really, you should be talking to customers, researching your product stuff. Really starting off by saying, I'm going to learn the strategy, whatever strategy my company already has, and I'm going to do my research, but I'm going to deliver on that strategy. But all this time while you're doing your regular product work, so you're visiting customers and you're analyzing data and all these things, you're probably having ideas pop up in your mind. You're starting to notice trends, you're starting to notice like what are the pain points people have and just stay open to that. And after about six months, I think is when you can start to put together a draft of a strategy for your own team. So this, I think you can take half a day, right? Just like block it off, don't take any meetings, you know, put on your headphones, go to a coffee shop, whatever it is that as you do to kind of get your alone time and just work on whichever of those three pillars of strategy, whether it's the vision, the strategic framework, or the roadmap. Start with whichever one draws you the most and start writing some stuff down. Just start getting your ideas out there. And this will start to give you that framework. You can then try to take that time, fill it out more, figure out what questions you have. What would you need to know to decide which of these approaches is better? What are the open questions you have? and then you can have something to start meeting with the rest of your product triad. So the engineering lead, the design lead, any other key stakeholders you have on your team, and just start working with them and start to figure out how are we feeling about our strategy? One thing I love to look for is like repeated disagreements. Are there any times when like we're fighting over whether to add this feature? And I so strongly believe we shouldn't, and you so strongly believe we should, and it's just like ends up feeling like a battle of wills. Anytime you have these disagreements that feel really thorny or they feel like a disagreement in values, that's a sign that really have a disagreement in strategy and that it's worth it to sort of write down what your strategic framework is or what your strategic principle is and address the problem at that level rather than fighting over individual features or individual decisions.

It's such a good tactical tip of just like, if there's continued disagreement, that's a sign you either craft a strategy or maybe a principle, which are kind of like related but sometimes different, just like principles of the product or principles to the team. Great advice. And the point you made about not spending the first time, the first six months on strategy, I love that because a lot of PMs come in and they're like, oh, strategy, I'm gonna figure everything out, gonna tell us how to build this thing. This all sucks, everything y'all have done before. And so just that rule of thumb of not allowing yourself to invest deeply.

There for six months. Love that idea. Nice. Yeah, I think as a manager, you usually have a reason for hiring someone. And usually, at least in your head, you think you've hired them to sort of build on the strategy that that you've already created. And there will be room for people to create new strategies and change the strategy. But if they come in on day one saying your strategy is all wrong, like raises the question of like, well then why did you join my team if you didn't believe in my strategy? A lot of times people just want.

You to like help them execute. They're just like, come on, we know what we're doing. Let's just help us ship this thing and it's gonna be great. And a lot of people come in and are like, now let's just rethink it all. Let's take a step back. okay, last area that I want to spend some time on is around career and career growth as a product manager and product leader. And luckily he wrote a book called Cracking the PM Career. If you just have to boil down the best advice from the book to like one suggestion to a PM, let's say starting off in their career and then maybe a career, like mid career, what would that be?

I'll start with one piece of suggestion for people at any stage of their career, which is to have a conversation with your manager. and say, I would really like at some point in the future to grow into whatever this goal is, whether it's to become a people manager, become a senior PM, become a director, whatever this next step of what you want is. So I would really love to become a people manager someday. What do you suggest that I work on now so that I'll be ready when the opportunity comes up? The reason I love this template, it's just a really easy way to start off this conversation of saying, like, here's my goal. Like, by the way, like, I do want to get promoted. I do want to grow. I want to Become a senior PM, I want, you know, whatever that next step is. I'm framing it in the future so that it's not threatening. It's not like gonna put my manager on the defensive and be like, you,'re not ready to be a manager yet. Let me, I don't have to prove why you're not ready for that promotion yet, which is not the mindset you want your manager in. And then it kind of brings them onto your side. Can you help me out here? Like, let's you and me work together to get me this promotion. Like you and me work together to get me ready there. It brings them in onto your side. So now they'll be in the mindset of trying I'm going to help you, it will target the feedback that you get on what you need to do to get that promotion. Because so much of the time, I think the reason that success as a PM is hard is because you get a gazillion pieces of feedback. They're all true. It's all like, yeah, you know, in that meeting you said a lot of filler words, but that's not the thing that's actually holding you back from the next promotion, or it's not the thing that you actually need to improve at to get to that next step. And so being able to focus the feedback you get on what you're trying to achieve makes a huge difference and will really help make sure that you get that feedback. And at any company, either your manager is going to be the person who decides if you get that promotion. What they say is just true, like whatever they think you're missing is what you're missing, or there's going to be a committee, and if there's a committee, your manager's feedback matters a lot. And also if they've been at the company a while, they'll sort of know what they look for. If you have a new manager at a big company that uses promotion by committee, at any big company make friends with your manager's peers. Find someone who's been at the company a while, who's gotten someone promoted and ask them that same question. Get them onto your side to like get you the experience and the improvements.

You need to get that promotion. Amazing advice. I found that to be super helpful myself. And you're saying that applies to every role, right?

UPMs, it PMs, everybody. Yeah, I think you can use that in almost any role because everybody does have different gaps. But then to go into like early career people, okay, I think that working on a large company early in your career can be just really, really valuable. If you choose a small company and you know what's going to be super successful and you like pick the winner, like that can be better than working at a big company. But big or I'd say even medium sized companies can be really good here. But a company where you're going to be able to learn best practices, you're going to be able to grow your network. I think that these large companies really give you, and you'll also be able to make usually a higher salary that starts to build your nest egg. I think that that gives you like a really good foundation for anything else you want to do later in your career. And when you're early in the career, really to have that mindset of absorbing and learning how to be a great PM. One mistake I see people make early in their career is they like, they kind of are trying to overdo it. They're like, I like, they've been given some project. Usually as a early career person, you get assigned a pretty like narrow scoped constrained problem. They're like, Hey, can you make the print dialogue for our product? and the right answer to these narrowly scope defined products is not to invent a whole new print dialogue, right? It's not usually, a lot of times you've been assigned a problem where a huge creative solution is a bad idea. And so if you're in one of those situations, just like do the simple thing, get it done really well, and that'll earn you the trust to be able to take on bigger things in the future. But you don't need to be outstanding to like make it past the APM promotions. Like you just need to be doing like a solid good job. And later in your career, there's a lot more room for being outstanding.

What are some of the most common mistakes that PMs make early on in their career that hurt their career?

Yeah, so a lot of it is misunderstanding what the role is at different stages in the career and sort of misunderstanding what success looks like. So this can show up in a lot of different ways. Like one of them is there's lots of APMs who want to become people managers right away and they sort of poo poo all the like regular everyday work you need to do to be a good PM. And that comes across to a manager as like kind of like immature, certainly, but also just like you don't seem to understand or value what good PMing is. So I certainly wouldn't make you a manager. But also now it's a little hard to convince you to do your day to day job, which makes you a little hard to manage, which might mean put a little bit less of my energy into managing you. It ends up being a bad situation. for people, it's a lot better to sort of show some enthusiasm for the job you're supposed to be doing right now. Other ways that can work is just people sort of optimizing for the wrong things, like leaning in too much or too little, right? So one, some PMs I see get paired with a really strong designer and you sort of let your designer take the lead on everything. And now you just sit back and you're a note taker, right? And you're not contributing anything, you're not really driving anything, you're not adding your own ideas and making the team better. So that person needs to sort of Step up more to have to be somebody who's really contributing and adding and being a multiplier on the work of everybody else on their team. And then some people step in too much. They're trying to lead everything and they're crowding people out and they're not giving, you know, their engineers a chance to present at all hands. And they're burning bridges with their coworkers. And almost every company peer reviews is a huge part of your review cycle. And as a product manager, you need to get along well with the other people on your team. You'll be pushing them and encouraging them to get more done than they would have otherwise. But you don't want to do this by having everybody say like, I never want to work with her again.

So much of advice I find for early careers, just like, get shit done, make impact, just do your job, don't overthink it. If you're going to earn your right to move up and take on more responsibility, get promoted on that kind of stuff. And so I love that so much of it is just like, just do the work, just like be quiet, do the work, it's going to go great. A couple more questions before we get to our lightning round. So you've exited the PM career path at this point, and so I'm curious, what made you kind of decide to kind of go in a different direction? And then just like what's next? What's next for Jackie Bovara?

Yeah, I'm not sure that I've exited the PM career path. I really like working in offices with people, so I've been sort of waiting for an end to the remote work era. And once I find companies that are, you know, in person again, I definitely have some curiosity about that.

I might go back to in person work. Oh my God, I am imagine your LinkedIn is about exploding right now as people are listening to this.

I'm in San Francisco. Oh boy.

And then were you going to say something else or?

Nothing is settled, but I've been playing around with the idea about whether or not to update the cracking the PM interview book. It's lots changed. Some of the companies there are not the top companies anymore. Some top companies aren't in there. Some of the companies have changed their interview processes. So I think that could be a lot of fun to get that more up to date. Some of the changes that have happened in it interviews over the past years.

Amazing. I imagine many people will be very excited to see a second edition of cracking the PM interview. Okay, let us get to our lightning round. Okay, so I'm just gonna ask six questions and just tell me whatever comes to mind as we go through them real quick, and maybe we'll pull out a thread or two as we go through it. Are you ready?

Yes.

Okay. What's a book that you recommend most to other product managers other than your book?

I love getting things done. by David Allen.

Ooh, okay. Around productivity. I love that book. That was really transformative for me when I read it many years ago, and I still use a couple of those points. Awesome. Okay, getting things done, David Allen. Other than Asana, what's a company that you recommend to PMs that are looking for a new gig?

What are some companies that you're excited about potentially? So I'm not the most up to date with all of the companies, but I do think that Microsoft is pretty underrated. I had a I had a lot of fun working at Microsoft. I learned a lot of good strategy there. I think I got a really good.

Foundation for a lot of the rest of my career. Contrarian pick and they've been killing it. So that makes a lot of sense. Good choice.

What's like a favorite app right now for you? I have a recipe manager called Paprika.

I really like it. Ooh, does it have actual recipes or.

Is it like track other recipes you found? It tracks other recipes. You can save any URL and it'll extract the recipe from there. and you can do meal planning in there. You can turn things into a shopping list. You can use it across your phone and your computer for when you want to sit down and browse. But I find that I really enjoy just browsing recipes and a lot of them I'll never cook, but just the idea that oh, I could imagine cooking that. It's a lot of fun. It's a little bit like traveling.

Wow, good tip, paprika. Okay, and then who's someone that you love to follow on Twitter or Instagram currently that maybe people haven't heard of, or maybe they have.

I love Helen Rosner @hels, H-E-L-S. She's a food writer for the New Yorker, but it's a lot deeper than food. A lot of it gets into society and bigger topics.

Wow, I see a pattern here around food. Who's your favorite manager that you've had?

It's probably JR Adasana, who I worked for for gazillion years.

Any particular reason why?

I think there's gotta be a match. between you and your manager. And I think that we had a lot of mutual respect. And I think that I was really lucky in that he was absolutely amazing at vision. I was able to learn a lot of it from him. And there were a lot of places where I was able to help. So, you know, a lot of my early experience of even getting to learn strategy and vision was, you know, he was like, Jackie, can you help me with the slides for the vision all hands? And I would be doing busy work of putting the slides together. But then I could make some suggestions, I could ask some questions. And first year I was just basically doing slides. Second year, I had a little bit of shaping. Third year, he let me take the first stab at it and then he reviewed it. And so I think he was always willing to sort of help me grow and really saw it as a win-win where if I grew into something, then that would free up his time to take on something bigger and better. Awesome.

Sounds like an awesome manager. And then last but not least, what's a favorite interview question that you love to use?

I love to ask, tell me about a recent project that you're proud of. I feel like that a lot of interviews don't give people enough chance to shine, right? To talk about something that they did really, really well and hear about like what made it so good, what are they proud of, and how did they achieve those amazing results?

And then what do you look for in an answer there? Like what are a couple bullet points of a good answer to that?

A lot of it, I mean it's so different for every question, but I'm definitely looking for, I try to get something recent, so I want to be saying that like MAtches the level that they're applying for, right? So there's gonna be a really big difference between the way that an APM answers this question, the way that a director of PM answers the question. I look to see how did they think about strategy? What was their judgment on different choices? What was hard? I have a framework for this. So this is the PEARL framework for answering questions like this.

Okay.

Problem, epiphany, action, result, and learning. So it's a little bit like the star framework, but I kind of want to know, like, what's the problem that you thought was worth solving? Is that a problem that I think is big enough? What's your epiphany? What's the insight that you had? Do you notice something that nobody else did? And how valuable was it? So a lot of times that's what makes these PM stories so interesting is that like meeting with customers head on and they said one weird word and you dug into it and you learned this whole new customer need that no one else had seen before. And then there's gonna be the action, like what did you actually do to make this happen? And was it hard? Because usually it is hard, but understanding the ways in which it's hard and how you overcame each of those challenges. And then I like to, obviously, PMs should care about results and be picking, they should, the thing they pick that they're proud of should have good results or have at least results that they learned from. And then, yeah, that last part of learning, did you grow from this? Especially if it's a failure, which is like, lots of people love to talk about the products that failed, or sometimes the interviewer asks them to talk about a product that fails. But I don't want them to leave it at like, yeah, it was a big loss. Our company lost $50 million and we couldn't get it back. But then you want to say like, okay, but what I learned from that is now I need to always run a load test on a staging server. And then I've had many successful launches since then that we like didn't have that same problem.

And wow, what a fruitful lightning round. So many nuggets. We got a new framework in there too. Okay, where can folks find you online?

And then any last words of wisdom? Yeah, I'm on Twitter @jackiebo. I'm on Twitter all the time, so.

Send me a message, I'll probably see it pretty fast.

Amazing. Thank you so much for being here, Jackie.

Yeah, thanks for having me. Great conversation. That was awesome. Thank you for listening. If you enjoyed the chat, don't forget to subscribe to the podcast. You can also learn more at lenniespodcast.com.

I'll see you in the next episode.