June 16, 2022

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

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

Jackie Bavaro is the author of the best-selling books Cracking the PM Interview and Cracking the PM Career. She was most recently at Asana, where she joined as its first product manager and later became the head of product. Earlier in her career, Jackie was a PM at Google and Microsoft, where she worked on high-impact products such as Google Search and Microsoft SharePoint.

In this episode, we cover:

1. How did Jackie become head of product at Asana? Start writing the best-selling PM books on interviews and the career ladder?

2. How and why to find a product coach.

3. What are the downsides of being a manager? How do you know if you want to go into management?

4. Can you stay an IC vs. becoming a manager?

5. What is “strategy”? What are the 3 components of a strategy?

6. What makes a good/bad strategy?

7. What are some ways to get better at strategy?

8. When should you start to invest in building your strategy muscle?

9. What are signs that your strategy is off?

10. What’s Jackie’s best piece of career advice?

11. Why is it smart to join a big company?

12. What are some of the most common mistakes PMs make early in their career?

13. What is the one thing Jackie thinks every PM should do regardless of their level?


Where to find Jackie:

- Twitter: https://twitter.com/jackiebo 

- Books: Cracking the PM Interview and Cracking the PM Career: https://amzn.to/3If6X9U

- Medium: ​​https://jackiebo.medium.com



- Jackie’s book rec: Getting Things Done, by David Allen

- Current favorite app, Paprika: https://www.paprikaapp.com

- Favorite Twitter: https://twitter.com/hels 

- PEARL framework: https://jackiebo.medium.com/interview-tips-for-senior-pms-2424f7b7c967

- Eigenquestions: https://coda.io/@shishir/eigenquestions-the-art-of-framing-problems


Thank you to our amazing sponsors:

* Flatfile: www.flatfile.com/lenny

* Amplitude: www.amplitude.com

* PostHog: www.posthog.com/lenny

Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe


Lenny (00:05):

If you're 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 cannon, 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 and 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 PMs. A big thank you to Jackie for sharing her wisdom with us.


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

Jackie Bavaro (03:01):

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.

Lenny (03:08):

Absolutely. It's my honor. Okay. You are a famous PM in the world of product management. You rode 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.

Jackie Bavaro (03:08):

That's awesome.

Lenny (03:26):

Yeah. And then also you've written a bunch of classic PM post on Medium that I reference often 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 left to start. Could you just 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?

Jackie Bavaro (03:47):

Yeah. I was just really lucky in finding product management. I went to Cornell, studied computer science and economics, and I'd never heard of the job. One of my friends who'd been a PM intern the summer before I was like, "Jackie, you have to apply for this internship." And I said, "I'm sophomore. I can't be a manager." And they're like, "No, you manage the product, not the people and just go apply." I applied having no idea at all what the job was. Through the interviews, I tried to figure it out. 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, that I started to think about changing companies.


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. 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 one of the biggest mistakes in my whole career. But looking back, it certainly is what gave me the impetus to write these books and say, "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 be 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 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. Number one, number two, number three." And then when I paid attention to my notes, I'd be like, "Wait, their three ideas weren't actually good ideas. They just sounded like they knew what they were doing." Those really drove me to want to share more about how to do well in these interviews.


And at the same time, I constantly had people saying, "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 help them understand the interview process. And after doing this three times, I was like, wait a second, "If it's only my friends of a friend who are people who work at Stanford and are already very privileged and I'm telling them how to pass these interviews, that's not fair."


If I'm willing to tell it to a friend of a friend, I have to be willing to put that out on the internet and share that with everyone, because we really want to level the playing field that we don't want to make things more unfair.


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. 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 and he is like, "Hey, it's like, imagine if SharePoint was really fast." And I was like, "Oh." I love 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 and achieve.

Lenny (06:32):

There's so many things I want to pull on in what you just shared there. On the book, an interesting point you made is that you 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, it's just like, "Oh, I had this question and this a way for me to get better at it by forcing myself to write about it." Is that basically what happened?

Jackie Bavaro (06:53):

Yeah. I 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.


That's 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 a lot of these interview questions are trick questions. When they say, "Oh, how would you design a bathroom?" I used to think that meant, "What do you want in a bathroom?" And that's not what it means at all. It means "Who is the best customer for a bathroom? What would they want?" But if you haven't been trained in this, you wouldn't know.

Lenny (07:34):

We're definitely going to talk about interviewing and career and come back to these topics. But going back to Asana, you look at this journey that you took and it sounds amazing and it went great, and someone that's 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?" A question is just, is there a mistake or some wrong journey took along this journey that you can share?

Jackie Bavaro (07:58):

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 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 never get anything important done if we just said yes to them. I need to say no to people." And I 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 right?" And 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 going to do that." And he's like, "Jackie, you have to stop shutting me down." And I was like, "I'm about to get fired." I was like, "Oh, I have really, really messed up here." It definitely made an impression on me and I was lucky enough to have a coach at the time. I went to her to talked to her and really started to rethink how I saw the role, this urgency that I felt of "I need to shut people down as fast as possible to the save time," as opposed to 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 exploring and brainstorming around that.


It wasn't an immediate change, but I remember at one point she challenged me to, "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. You can say, 'yes, I agree. That is a real problem. 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 protectiveness and lockdownness that I had really wasn't something I needed and it wasn't something that was serving me because it meant that I couldn't have real collaboration with the other people around me.

Lenny (09:51):

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 is a fundamental thing that I imagined isn't maybe as true as I thought in changing course there." Maybe let me ask that question, how far into your career was that?

Jackie Bavaro (10:10):

This was probably pretty early. I'm imagining what room it was in and I'm like, "Okay. I know what that time was." It was definitely the first year, maybe six months in.

Lenny (10:17):

Okay. Okay. Cool. Okay. So you have this coach, what 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.

Jackie Bavaro (10:31):

There's two different models. 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 just bounce ideas off of all the time, have this person who isn't in any way going to be the person who evaluates them later on. 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 want to work on. I tend to be a little bit results oriented, action oriented, and I don't like to show up and be like, "So, what are we talking about today?" Or make something up. I talked to this coach to deal with this issue of 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.


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 bring it to the coach, and then all of a sudden it felt like it was a big deal rather than a little deal. I've gone in and out of coaching, but I do it when I have a thing that I want to work on.

Lenny (11:27):

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?

Jackie Bavaro (11:35):

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. 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. It felt like we were moving really slowly. Customers hated how slow the app was and this framework changed was needed to change that. But we really were not sure that the company was going to be successful.


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, the planning committee. The planning committee was 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 "Okay, here's the direction we have. Here's what you're going to need to do." And I had to ask some questions and I'd be like, "Well, what about this? And what about this?" After a little bit of time, I would start to be like, "Hey, you have your planning committee today. Here are the three questions I want you to go in and get answered at that committee. And if they say this, I want you to 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 save you some time and some energy if I just joined you." And it was a way that I took myself into this higher level meeting, framing it as something that was going to 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.


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 building features. Going from features to strategy, but also understanding business strategy and 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 our office.


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 background and my deep knowledge of this product, that I was able to be exposed to this and have these responsibilities.


For me, I really felt like I was learning and I was growing and I didn't know it all yet. That's really kept me there for a long time. And then I'd say, getting closer to the end of that time, I'd become a manager, I had teams, I've become a manager of managers and I was definitely starting to get burned out. It's really, really tough being a manager. One of the ways that I'd always worked as a product manager is a lot of transparency and authenticity. A lot of explaining to people what our goals are and then showing like "This is the solution I think will hit in our goals, but I'm open to other solutions."


As a manager, there are times when my goal is backfill for someone I know is quitting in a few weeks, but I can't tell anyone about it. Or there are all these personal secrets that you have to keep for people as a manager. And there are times where, what the person on IT wants is a promotion to make more money, and haven't necessarily earned it yet. And it's not necessarily the right thing to do from a company perspective.


Those places where you're torn between these two goals or what I want, isn't always perfectly aligned with what's best for the people that report to me, that weighed a lot on me. That was very heavy.


I was like, "Okay, maybe I could use a break." But for a while I felt like, "Okay, but I don't want to just leave the company and things 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, "Everybody's doing great. They don't need me. They can do fine without me." And I thought about, I just felt this surge of energy thinking, "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. That's how I knew it was time to leave.

Lenny (15:44):

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 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."

Jackie Bavaro (16:01):

Definitely. Tooth directions I would say. One is just 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. It's more painful and less fun. For all these reasons, you might not want to be a manager. At the same time, I'm like, "Well, what could I have told younger Jackie, to be like, maybe you don't want to be a manager," and there's nothing. There's nothing you could have told me that would've convinced me not to be a manager. I might say that if you want to try it, consider it a two way door, consider a time 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.


When I started as a product manager, I had no idea what salaries people made, none at all. And I knew I wanted to be able to support a family and stuff when I grew up. So I assumed that I needed to make it to junior VP level to be able to do that. And I just had no idea what salaries were like. Since then, I've looked at 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 senior PM, which is one of the middle levels, this middle senior PM level at 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 making a lot of money. You don't necessarily need to climb that career ladder forever to make a lot of money.


And especially at a company like Google, there's a few companies that are known for being the highest paying companies, you can make a lot of money. Much more that you can make in a lot of startups, just by being in IC path, just by continuing to do that job. And companies really need people to do that.


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, 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.

Lenny (18:05):

Along those lines, I know a lot of companies in theory have these kind of IC 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 what you see too? Or, I don't know, is there a way to actually be really successful going down that path?

Jackie Bavaro (18:22):

Yeah. 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 a director, but with the team that's small enough that they can PM the whole team. And there's only a few problems out there like that. Platform type teams can fill that role a lot of the time. Partnerships, someone 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're a manager of managers and you 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 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. 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 with other 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, 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. There are a career path that is just not climbing the career ladder.

Lenny (19:55):

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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 an infrastructure team or a new business unit, unlikely to be a user facing piece, because they probably want to build a large teams there with a lot of layers. Interesting. Great stuff.


Okay. I want to transition to strategy. You've written a lot about strategy. I share your pieces often with folks. Diving into that a little bit, first of all just, can 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?

Jackie Bavaro (21:21):

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. I was like, "Okay, great. What does being more strategic mean?" And nobody could tell me. And 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 those managery stuff." And I was like, "Okay, I have no role models, no words, nothing to explain what it means to be more strategic." Quick shout-out to my book is, I've got a whole list of what it means to be more strategic. So if you pick that up, you can read through that.

Lenny (21:51):

Can we find that on Amazon? Where do you find that book?

Jackie Bavaro (21:54):

Yes. Just the Cracking the PM Career, that's on Amazon.

Lenny (21:57):


Jackie Bavaro (21:57):

And it's in the strategy chapter.

Lenny (21:59):


Jackie Bavaro (22:00):

What I did is I wrote a document 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 just random... What my plan was. But once I wrote it down and shared it with people, then I started getting feedback on it. And then I could start to feel my way to what people meant to strategy. Then I get to Asana and I worked 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. We talked about this idea that when you're playing guitar, you're left and your right hand know how to work together to play the guitar. 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 you worked seamlessly together?


And Asana was the team brain helping this happen. 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 as you kept track of your own task that updated the centralized system, that was always up to date.


We had this vision of what the future could be like. And we had our strategy, which got into this team brain. And what's what a good team brain have? Well, has to always be with you. So we need to have good mobile and good security, needs to know about the different kinds of work that exists. So we need to... 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. 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. 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 it is. 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, again, find out that I don't know it." We had a lot of conversations and 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.


Three parts of strategy are your vision. 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 come join me, come build this future with me? Won't this to be exciting?"


And then you've got your strategic framework. 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." That's where you get your pillars, and it's your unique way of breaking down the problem to understand who you're going after and what it takes to win them.


And then the third part is the roadmap. This is where you work backwards from your vision. You say "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."


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 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 probably your strategy did not actually fit into the timeframe that you wanted and that roadmap helps you see like, "Okay, what would it take?" And then that can be a little bit of an organizing factor for people across the company to understand, "Okay, we're having a major launch in two years, then we need to make sure that we're going to 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." It really helps kind of pull the pieces together.

Lenny (26:00):

Wow, that's so actionable and easy to understand. I've never heard it describe so simply. Along those lines, say someone creates a strategy, what are signs that it's a good strategy versus a meh strategy? Which should they be looking at?

Jackie Bavaro (26:15):

I'm probably going to write something on this soon. In the past month, I'd actually have 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 increased revenue by 50%, it's a revenue target number. That doesn't seem like a strategy to me. I don't know what to do." Talking to people, I started to get a deeper sense of what the confusion and the mismatch is here.


I think a good strategy is all about connecting the dots. Connecting the dots from this high level business goal of, "We want to increase revenue by this much" to, "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 "Given that this is our big picture of view of what we're doing, what's the next step? And what's the next step? And what's the next step?"


"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. 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 maybe 20 different things your product team could work on. 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 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? I think this will make us the 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."


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 could 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?"


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. So you have to pay really, really close attention to find those missing assumptions so that you can then explain why this connects to this.

Lenny (28:51):

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

Jackie Bavaro (29:02):

Yeah. Strategy really should be collaborative work. I think that there's 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 strategy should be very collaborative.


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. Sometimes it's as easy as a conversation. 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 which of the five pricing models did we think was best. And I think I was like, "Number three is most [inaudible 00:29:44] 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 a mind. You're right. You just saw it in a way that I hadn't seen."


This accumulation of experiences, I think matter so much for strategy, for data analysis, all of these things where... I'm really, really good at data analysis, but only because I've seen so many experiments that when I see a set of results, I can just instantly remember like four similar experiments and 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." 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 a bunch of leaders sitting in a room talking to each other.


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 iterate, like being one doing 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. 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.

Lenny (31:06):

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

Jackie Bavaro (31:27):

Yeah. Definitely there's a lot of cross applying of strategy that I think that really is helpful. One of the great ways to learn strategy is to cross apply strategy from other places. One of the people I interviewed for my book was to Shishir Mehrotra, 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, 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?" 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.


I think having that broad view and looking at lots of other products and seeing how they make their choices and how do they frame their decisions, that's a good way to improve strategy.

Lenny (32:49):

That's a really good reminder of eigenquestions as a framework. I think if you Google eingenquestions, you can find it and I'll try to link it to it in this podcast. And Shishir has a lot of great stuff that he's put out there. Good call out.


Let me ask one more quick question on strategy and then I want to move on to career stuff. How long should people, I guess, early PMs maybe, how much time should they spend on strategy development? And then, when does it make sense to start investing in that?

Jackie Bavaro (33:15):

Yeah. 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 are probably having ideas pop up in your mind. You're starting to notice trends. You're starting to notice 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.


I think you can take half a day. Just block it off, don't take any meetings, put on your headphones, go to a coffee shop, whatever it is you do to 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 go 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. 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 repeated disagreements, "Are there any times when 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 ends up feeling like a battle of wills. Anytime you have these disagreements that feel really torny 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 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.

Lenny (35:11):

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 related, but sometimes different, just principles of the product or principles of the team. Great advice. And the point you made about not spending the first six months on strategy, I love that because a lot of PMs come in are like, "Oh, strategy. I'm going to figure everything out. I'm going to tell us how to build this thing. This all sucks. Everything you all have done before." Just that rule of thumb, of not allowing yourself to invest deeply there for six months. Love that idea.

Jackie Bavaro (35:42):

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 build on the strategy 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, raises the question of, "Well then why did you join my team if you didn't believe in my strategy?"

Lenny (36:06):

A lot of times people just want you to help them execute. They're just like, "Come on. We know what we're doing. Just help us ship this thing and it's going to be great." And a lot of people come in like "No, 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. Career growth as a product manager and product leader. Luckily you wrote a book called Cracking the PM Career. If you just had to boil down the best advice from the book to one suggestion to a PM, let's say starting off in their career and then maybe a mid-career, what would that be?

Jackie Bavaro (36:41):

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. "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 is just a really easy way to start off this conversation of saying "Here's my goal, by the way. I do want to get promoted, I do want to grow, I want to become a senior PM," whatever that next step is.


I'm framing it in the future so that it's not threatening. It's not like going to put my manager on the defensive and be like, "You're not ready to be a manager yet. 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 brings them onto your side. "Can you help me out here? Let's you and me work together to get me this promotion. 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 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. 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.


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, 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 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 to promoted and ask them that same question. Get them onto your side to get you the experience and the improvements you need to get that promotion.

Lenny (38:41):

Amazing advice. I found that to be super helpful myself. And you're saying that applies to every role. UPMs, everybody.

Jackie Bavaro (38:48):

Yeah. I think you can use that in almost any role because everybody does have different gaps, but then to go into early career people, I think that working at a large company early in your career can be just really, really valuable. If you choose a small company and what's going to be super successful and you pick the winner, that can be better than working at a big company. But big or, I'd say, even medium size 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 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 are trying to overdo it. They've been given some project, usually as a early career person, you get assigned a pretty 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.


A lot of times you've been assigned a problem where a huge creative solution is a bad idea. If you're in one of the situations, just 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 make it past the APM promotions. You just need to be doing a solid, good job. And later in your career, there's a lot more room for being outstanding.

Lenny (40:20):

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

Jackie Bavaro (40:25):

Yeah. A lot of it is misunderstanding what the role is at different stages in the career and misunderstanding what success looks like. This can show up in a lot of different ways. One of them is, there's lots of APMs who want to become people managers right away, and they poo poo all the regular everyday work you need to do to be a good PM. And that comes across to a manager as 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 show some enthusiasm for the job you're supposed to be doing right now. Other ways that can work is just people optimizing for the wrong things, like leaning in too much or too little. On PMs I see get paired with a really strong designer and you let your designer take the lead on everything. And now you just sit back and you're a note taker and you're not contributing anything. You're not really driving anything. You're not adding your own ideas and making the team better.


That person needs to step up more, 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 too much. They're trying to lead everything and they're crowding people out and they're not giving 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 in your team. You'll be pushing them and encouraging them to get more done than they would've otherwise, but you don't want to do this by having everybody say, "I never want to work with her again."

Lenny (42:06):

So much of advice I find for early careers, it's just like it should done, make impact, just your job, don't overthink it, if it won't earn your right to move up and take on more responsibility, get promoted on all kind of stuff. I love that so much. It's just do the work, just be quiet, do the work, it's going to go great.


A couple more questions. And before we get to a lightning round. You've exited the PM career path at this point, and I'm curious what made you decide to go in a different direction? And then just, what's next? what's next for Jackie Bavaro?

Jackie Bavaro (42:35):

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

Lenny (42:51):

Oh my God. I'm imagining your LinkedIn is about exploding right now, as people are listening to this.

Jackie Bavaro (42:57):

I'm in San Francisco.

Lenny (42:59):

Oh boy. And then were you going to say something else?

Jackie Bavaro (43:02):

Nothing is settled, but I've been playing around with the idea about whether or not to update the Cracking the PM Interview book. 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. I think that could be a lot of fun to get that more up to date. Some of the changes that have happened in interviews over the past years.

Lenny (43:21):

Amazing. I imagine many people will be very excited to see a second edition of Correcting the PM Interview. Okay. Let us get to our lightning round. Okay. I'm just going to 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?

Jackie Bavaro (43:39):


Lenny (43:40):

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

Jackie Bavaro (43:45):

I love Getting Things Done by David Allen.

Lenny (43:47):

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 this 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?

Jackie Bavaro (44:06):

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 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.

Lenny (44:19):

Contrarian pick and they've been killing it. That makes a lot of sense. Good choice. What's a favorite app right now for you?

Jackie Bavaro (44:25):

I have a recipe manager called Paprika. I really like it.

Lenny (44:30):

Ooh. Does it have actual recipes or is it track other recipes you've found?

Jackie Bavaro (44:34):

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 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.

Lenny (44:58):

Wow. You could say 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.

Jackie Bavaro (45:06):

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.

Lenny (45:19):

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

Jackie Bavaro (45:23):

I think it's probably JR at Asana who I worked for gazillion years.

Lenny (45:28):

Any particular reason why?

Jackie Bavaro (45:29):

I think there's got to 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 from it from him. And there were a lot of places where I was able to help. A lot of my early experience of even getting to learn strategy and vision 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. I think he was always willing to 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.

Lenny (46:20):

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

Jackie Bavaro (46:26):

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

Lenny (46:46):

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

Jackie Bavaro (46:46):

It's so different for every question, but I'm definitely looking for try to get something recent, so I want them to be something that matches the level that they're applying for. There's going to be a really big difference between the way that an APM answers this question and 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. The pearl framework for answering questions like this is problem, epiphany, action, result and learning.


It's a little bit like the star framework, but I want it all like, "What's the problem that you thought was worth solving, 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?"


A lot of times that's what makes these PM stories so interesting. Is that meeting with customers, head on and they said one weird word and you dug into it and you learn this whole new customer need that no one else had seen before. And then there's going to 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 obviously a PM should care about results and 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 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 "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 didn't have that same problem in."

Lenny (48:29):

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?

Jackie Bavaro (48:38):

Yeah. I'm on Twitter, @jackiebo. I'm on Twitter all the time. Send me a message, I'll probably see it pretty fast.

Lenny (48:44):

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

Jackie Bavaro (48:46):

Yeah. Thanks for having me. Great conversation.

Lenny (48:49):

That was awesome. Thank you for listening. If you enjoyed the chat, don't forget to subscribe to the podcast. You could also learn more at lennyspodcast.com. I'll see you in the next episode.