January 17, 2023

The Jackie Bavaro Hypothesis: Cracking the PM Career Means Leading With The Right Questions

In this episode of the Product Science Podcast, we cover why Jackie wrote books about PM interviews and careers, how product organizations evolve as a company grows, and what great product leadership looks like.

The Jackie Bavaro Hypothesis: Cracking the PM Career Means Leading With The Right Questions

Jackie Bavaro has over 15 years of product management experience, most recently as Head of PM at Asana. During her tenure, she grew the PM team to over twenty people, helped Asana's go from 0 to more than $100 million in annual recurring revenue, and launched Asana's associate product manager program. She has worked as a PM for Google and Microsoft as well, and in a diverse set of PM roles—consumer, B2B, platform, mobile, and growth. She has been a manager and manager of managers. She has written two books: Cracking the PM Interview and Cracking the PM Career. You can find her on Twitter at https://twitter.com/jackiebo and substack at https://jackiebavaro.substack.com/.

In this episode of the Product Science Podcast, we cover why Jackie wrote books about PM interviews and careers, how product organizations evolve as a company grows, and what great product leadership looks like.

Subscribe for the full episode on Apple, Google Play, Spotify, Stitcher, YouTube and more. Love what you hear? Leave us a review, it means a lot.

Resource Links

Read Cracking the PM Interview

Read Cracking the PM Career

Follow Jackie on Twitter

Follow Jackie on LinkedIn

Follow Jackie on Substack

Follow Holly on Twitter

Follow Holly on LinkedIn

Questions we explore in this episode

How did they do product strategy at Asana?

  • There was an upfront product vision of where they thought the future could go and then broke it down.
  • They built a strategic roadmap to break the vision into big pieces that both deliver as much value early as possible and also validate their ideas as they went.
  • They used a strategic framework that focused on who would be buying the software, what they care about, what is their market, and what it takes to win.

How did the team change over time at Asana while Jackie was head of PM?

  • They started off with very few approval processes because they wanted to trust their people and give them
  • Eventually, they landed on the double diamond product process with checkpoints at each of the key moments.
  • As the company grew, it split into product pillars when the company had grown to a size where it needed an additional layer of organization.

What were some of Jackie’s learnings about being a product leader?

  • As a Head of PM you spend about half your time growing and guiding your team and about half your time with other department leaders as a voice that cares about the company.
  • Instead of giving people the answer, she needed to include them in the creation of the answer so that they were bought in and motivated.
  • Great roadmaps aren’t just a stack-ranked list of features but rather use a portfolio approach, which she likens to a charcuterie board.

Quotes from this episode

What does it take to succeed at that vision? What does it take to get us to the place that we want to go? And that's where you come backwards to both the strategic framework and the strategic roadmap…you figure out how to, how to move the big pieces to both deliver as much value early as possible and also validate your ideas as you go. And that strategic F of work is the third part of strategy, which is where you figure out what's our market and what does it take to. Who are the people who are gonna be buying this and what do they care about?
Eventually we ended up at a point where we followed double diamond product process and we had checkpoints at sort of every key point in the double diamond. You do some discovery work and then you present your research findings. You narrow in on definition and then you sort of present your one page spec of what problem you wanna go after you widen exploring lots of different designs, different ways to solve the problem, maybe do some user research there, and then you sort of present early design review. And then we'll narrow in again on like, here's the design that we actually want to build. That will get the reviewed as well. And of course along with us also the engineering parts and then a final launch review.
Even though I was head of pm, half my job is being a great leader of the PM team, and the other half of my job is being in meetings with other leaders at the company with other head of design and other people, and talking over the tough problems that we were having. Not only representing product in those rooms, but just representing another smart person who cared about the company.

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Holly Hester-Re...: Hi, and welcome to the Product Science Podcast where we're helping startup founders and product leaders build high-growth products, teams, and companies through real conversations with people who have tried it and aren't afraid to share lessons learned from their failures along the way. I'm your host, Holly Hester-Reilly, founder and CEO of H2R Product Science.

This week on The Product Science Podcast, my guest is Jackie Bavaro. She has over 15 years of product management experience, most recently as head of PM at Asana. During her tenure, she grew the PM team to over 20 people, helped Asanas go from zero to more than 100 million in annual recurring revenue and launched Asana's associate product manager program. She has worked as a PM for Google and Microsoft as well, and in a diverse set of PM roles, consumer, B2B, platform, mobile, and growth. She has been a manager and a manager of managers. She has written two books, Cracking the PM Interview and Cracking the PM Career. You can find her on Twitter @jackiebo and on Substack at jackiebavaro.substack.com. Welcome, Jackie.

Jackie Bavaro: Hi, thanks for having me.

Holly Hester-Re...: I am so excited to talk to you today. I came across you when I first started consulting and I remember reading some of your articles about how you did product at Asana and just thinking, "This is really great stuff." So, I'd love to hear more about your journey. How did you begin getting into product management?

Jackie Bavaro: So, I got into product management right out of college. I was one of those lucky people who I was looking for a summer job, handed over my resume to all of the people at the engineering recruiting fair, and none of them called me back. And a friend finally said, "Jackie, you need to apply to this PM job," and just kind of pushed me into the first interview and that's how I got an internship at Microsoft.

Holly Hester-Re...: Oh wow. For people who've been in product 15 years, it's very rare to hear that story, that they came right out of college. So, what was that first PM role at Microsoft like?

Jackie Bavaro: So I was a PM on the SharePoint team, and it was very exciting. I was on a team with 15 other PMs. It was shipping software that ships on a DVD, which is very different than the way that you ship software where you could update it every single day. And I had incredible managers, incredible mentors, and learned a lot there. I probably would've stayed there for a very long time if I hadn't wanted to move to New York.

Holly Hester-Re...: So, what brought you to New York?

Jackie Bavaro: So I had family in New York and, yeah, when I wanted to move there, Microsoft didn't have any PM jobs there. So that's when I applied to the Google APM program for the first time, but I got rejected after two phone interviews.

Holly Hester-Re...: Oh yeah? Tell me more about that because I love to hear from people about the difficulties they've faced as well. So, how did that experience go for you?

Jackie Bavaro: Yeah. So I was doing really well at Microsoft, so I thought I was a great PM and I was kind of shocked when I got rejected after those phone interviews. And I think that really sort of set the stage for what eventually convinced me to write a blog and then a book on product management interviews because I realized only after the fact that I had answered these questions just completely incorrectly. I had sort of rambled on, spoken conversationally, misinterpreted what they were getting at with the questions themselves. And then I found out that other people, especially people who were applying for management consulting, that they had books that they were studying for learning how to answer these questions, because I'd also applied to some management consulting firms. And I was kind of shocked to realize that I'd been going in blind just trying to figure it out as I go, and other people had been prepped for this. So, that really made a big influence on sort of how I saw the world of product management.

Holly Hester-Re...: How did you figure that out by the way, that other people had been prepped for it?

Jackie Bavaro: Case in Point is the management consulting book. I think I saw it on one of my coworkers' desk eventually, and I was like, "Oh, what's that?" And she said, "Oh, it's the book you use to study for management consulting," and I was like, "What?" And I flipped through it and I was like, "Oh. Oh. Oh, no wonder the questions they'd asked me seemed unsolvable." At management consulting, they'd handed me a table of numbers and said, "How can you make this company make more money?" And I had no idea how to even begin. I'd never heard a question like that. And I hadn't known that you're not supposed to go into these interviews without any prep. So, it really sort of showed me how unlevel the playing field was and really made me want to kind of go in and make that something that was more broadly known.

Holly Hester-Re...: Yeah. So, what did you do? Did you come to New York soon after that or was it a while?

Jackie Bavaro: So, I took a different job at Microsoft for a year. I was on Microsoft Consulting Services and I kind of pretended that I was on an extended user research stint. I just kind of was doing work for different people, but kind of watching how they used products and realizing how differently real customers use our products than I had expected when I was designing the products. And then a year later I applied again, and that time I got into Google and then was able to join the APM program then.

Holly Hester-Re...: So, how did the second time differ from the first time in terms of your preparation and your approach?

Jackie Bavaro: Well, I hadn't yet learned about the prep, so I think I just got lucky that second time.

Holly Hester-Re...: That's awesome. Love it. Okay. And then once you got in, what was that like?

Jackie Bavaro: So, Google is very different than Microsoft. I feel very lucky that I got to work at two different companies and really see how differently they approach the work. And Microsoft, there's a lot of planning, a lot of strategy. And as a new PM, by the time you sort of show up on a team, you have a very fixed playground in which like, "This is your area that you own. And we know this is going to be important, so we've kind of added the constraints so that now you can kind of do what you want in this playground." And if you have an idea there where you're like, "Oh, there's something totally different I would like to do," it is very, very hard and you're fighting against the company, sort of you're fighting against your team sort of the whole way.

So I had a few things that I did at Microsoft like this where I thought we really needed Firefox support for SharePoint, which was a browser app. And I basically had to make friends with engineers and convince them to do this work for me on the side. And we were kind of keeping it secret and it was trying to help make sure that they wouldn't get in trouble with their boss for not doing the work they were supposed to be doing. And it ended being a very, very important piece of work, but it was not seen as a good thing that I was here stealing engineers' time to work on my side project.

Holly Hester-Re...: Yeah. So, wait, before you go on, tell me more about that. I guess with what you know now, would you do it the same way again?

Jackie Bavaro: I think that it's important to understand how things get done at your particular company. I think my impression at the time was that I was doing something wrong and something secretive. With what I know now, I might have done the same thing but felt a little bit better about it because I do think that having been a manager and understanding what a manager's job is, and how can the people that work for you help you with your job, and how can they hurt you, a lot of my managers would really support something like this. And as long as I could do it sort of in line. So, for example, one of the top things I tell people is just understand the cadence of planning at your company. So understand when does the team decide on new features because that can be weeks or months before the features actually get built.

And so if you have an idea, you need to share that idea at the right time. So I had another feature I really, really wanted to get built, wikis into SharePoint, and I was talking about it to everybody nonstop, constantly sending over articles every time I heard about this, just kind of being a pain about it. And then nothing happened. And then it was just about time when the interns were going to show up and then they were like, "Hey, we have some extra interns, they need a project. Do you want them to work on wikis?" And that was the timing was right and that's when it ended up working. And I think that planting the seeds earlier helped, but I was getting discouraged. And if I had understood how the timing of when the team can pick on new projects works, I think I would've had sort of a smoother way of getting that in.

Holly Hester-Re...: Mm-hmm. That makes sense. So, those are some interesting stories from your time at Microsoft. Tell me more about what you worked on at Google.

Jackie Bavaro: So at Google I started on the data APIs team, and this was the team that was building the infrastructure that things like the Google Calendar API were built on top of. And I showed up and I was like, "So, what should I do?" And the tech lead says, "What do you think you should do?" And it was a world of different from Microsoft where everything had been planned and they knew exactly... Here, they were just sort of like a PM was inflicted upon the team and they were like, "Well, I hope she can find something useful to do with the team." So I think in terms of building my autonomy, that was a shock, but it was a really good experience. And it just kind of illustrated how different the Google culture being sort of engineering led and hire a bunch of smart people, let them do what they want and trust that we've got enough smart people here that some of them will come up with really valuable things.

And so that ended up being a lot of my Google experience. And I think that as an ambitious person, it was a great place to work because when I did have something I really wanted to do, it was clear that the company sort of supported me in trying to push my big idea forward. But at the same time, I saw it be really discouraging for some people who were encouraged to push their big idea forward even though this big idea had no chance of launching and they would get many months into the work they've done only to get their project shut down.

Holly Hester-Re...: Interesting. So, what was the first idea you got passionate about when you were working at Google?

Jackie Bavaro: I guess the one that I am most proud of is... So, I went from the data API team to the search team. And when I went to the search team, I was scared to switch to this team at first because everybody knew you had to be really analytical to work on Google search. And I thought that I was not analytical. So, I mentioned I had totally failed these management consulting interviews where they gave me a table of numbers and I thought that's what analytical is. And I knew also these questions of like, "How many pizza shops are in America?," and I hated those, just didn't know how to start with them. And so I thought that I was not an analytical person and I was scared to go onto this team, but I figured, "Be brave. The only way you'll learn is if you actually try it."

And when I got to the team, I realized that being analytical does not mean that you can stare at a table of numbers you've never seen before with no context and pull out, "How does this company make more money?" But what it does mean is that you can sort of take a large ambiguous problem, break it down into small enough pieces that now you can get data on those pieces, figure out what pieces of data might be interesting, and then look at this data that now you have a lot of context on. And from there, figure out, "How could this company make money?," or things like that. So, for example, the two ways we really use data analysis on the search team, one of them was on coming up with ideas of how to improve our algorithms.

So a thing that I very frequently did was I have a version of SQL and say, "Give me 1,000 random queries from yesterday," plug it into a tool that would just let me click through and see what the results look like for each of those, and just scan through them as fast as I could and just try to find patterns of, "Are we getting good results for each of these?" I specifically owned image results and local results and video results. So I would go through sometimes with all three of these hats or sometimes just one saying, "Should we have shown videos for this and we didn't?," or, "Should we have shown a local business and we didn't?" And that's being analytical.

And the other way we used being analytical was in looking at experiment results. So one of the experiments we did was if you searched for a person, like Kevin Bacon, we had some good signal that you wanted to know, "Who's Kevin Bacon?" And so a picture of Kevin Bacon is an amazing result. The problem with image results is that you show up, you get a great result, you're like, "Excellent," you close the browser, you're done for the day. And it looks to Google exactly the same as if you got a terrible result and you're like, "None of these are what I wanted. I'm just going to go ask on Facebook."

So that was one of the things where me with my team, and was really one of the engineers who drove this, just looked at every slice of data we could get for our experiment on this to try to figure out what data might be a little bit different. Data might be a little bit different to show that it was good for us to show images for Kevin Bacon, but bad for us to show... Oh, we searched for a truck, for example. Usually there you wanted the shop instead of see the actual which truck is it. And we just poured through probably 100 different ways of looking at the data until we finally were able to find some evidence that we distinguished good versus the bad cases.

Holly Hester-Re...: And what was that evidence?

Jackie Bavaro: In this case, it happened to be that for the people who didn't just do nothing at all, did a lot of them actually end up clicking through on those images? Because if the images were good or in the case where we hadn't shown images at all, had people actually been clicking over to that images tab? Because if the clicks we were stealing were clicks that were going to go to the images tab anyway, that's a good sign that it was positive. But if the clicks we were stealing, none of those would've gone to the images tab, they would've gone to a different website, then that's a sign that it was bad.

Holly Hester-Re...: That makes sense. So, how long were you at Google?

Jackie Bavaro: I was at Google for three years.

Holly Hester-Re...: Okay. And I hear a lot about sort of this idea that Google is for product managers, and I guess for engineers as well, a place where there's a lot more support for launching things than there is for maintaining things. And I'm curious if that's something that you saw.

Jackie Bavaro: So, my view on Google is that Google takes an investor view of the projects happening at Google. And so investors don't expect every single one of the projects at their company to succeed or every one of the projects they invest in. They want to invest in a wide variety of things so that they have a chance of investing in the product that's going to be 100x, that's going to be absolutely amazing. And so at Google, there's a lot of support for, "Hire smart people, let them build sort of whatever they want to build, and then let's see which of these succeed. Let's see which of these flowers bloom."

And so there's a lot of freedom to go and launch a brand-new product or try to launch a brand-new product. And you get that chance to say, "Maybe this is going to be huge." But then if you launch it and it's not huge, Google hadn't decided, "This is a really important product for us to launch. It didn't work the first time, but let's make sure that we're going to iterate on it until it gets somewhere good." They tend to have more of a, "Well, I guess that wasn't the 100x product that we were going to build. Let's divert our resources to the next product that has a chance of being 100x."

Holly Hester-Re...: I see. Okay. And do you think that that's different from other large enterprises that you've worked at?

Jackie Bavaro: Definitely. Very different than both Google and Asana. So at Google and Asana, I'd say that we're much more focused on product strategy. So Google has a company strategy, which is this investor view of the projects that they take. But there isn't a top-down product strategy at Google, at least as far as I saw when I was there. In fact, you could really tell this by the way the OKRs were done. So the way that OKRs happened at Google is every team made their OKRs, and then the best OKRs from a team were brought up to be that division's OKRs, and then the top 10 most important OKRs from those divisions across the company then kind of get promoted through the levels basically to get 10 company OKRs, which are really just 10 specific OKRs of teams or maybe groups of 10 PMs together at the most of, "This is the thing we're going to do."

So it was really a selection of the best individual OKRs became the company's top priorities as opposed to how it works with Microsoft and Asana, which is that there's an upfront vision of, "Here is where we want to go. Here's how we think the future could be a better place. And then let's break down, what does it take to achieve that vision?" In Asana, it was we really thought about this idea that there's too much work about work. There's all of this potential in people that's wasted and it's hard for teams to work together and people repeat effort. And wouldn't it be amazing if the teams at your company could collaborate just as easily as when you're playing the guitar, your left and right hand can work together? Right? It just sort of feels effortless in that way. So we had a vision, [inaudible 00:15:58] you that in the future teams would be working together to this ambient awareness of what other people were working on, what status everything was in, and get the support that they need to have everybody work well together.

So, that's the vision. And then from there you figure out, "Well, what does it take to succeed at that vision? What does it take to get us to the place that we want to go?" And that's where you come backwards to both the strategic framework and the strategic roadmap. So the strategic roadmap is sort of working backwards and saying, "Okay. Well, if we want to be there in five years, here's what year one looks like, year two, year three, year four, year five." And you kind of look at it and you're like, "There's no way. That's 20 years of work." And you realize that you need to focus and bring it in and say, "Okay, actually we're going to switch it over to here." Or you put that plan together and somebody's like, "No, I think that augmented reality needs to come much earlier in that roadmap," and you figure out how to kind of move the big pieces to both deliver as much value early as possible and also validate your ideas as you go.

And that strategic framework is the third part of strategy, which is where you figure out, "What's our market and what does it take to win? Who are the people who are going to be buying this and what do they care about? What are our strategic principles for how we think about what this product is?" So at Asana, we thought about the idea that, just like your human brain coordinates your left and right hand, Asana is your team brain that's coordinating all of the work that happens in your organization. And so this is sort of early days, but our strategy, we sort of created these product pillars that said, "Well, what does a good team brain need to have?" Well, it needs to know about all the different kinds of information about work. So we would say, "Okay, we're going to have variety of projects we do to make it so that Asana can understand more types of work."

But a good team brain needs to help you draw insightful connections. And so being able to visualize how your project is going or get alerts when things are off-track or get suggestions on how to do better on your project. And so we had a whole set of work there. And a good team brain needs to always be with you. So, it needs to have a mobile app and it needs to have good stability and it needs to have security so that you don't lose your data. And so we can sort of take all of the work that you might do, but group it in a way that really illustrates what we're trying to achieve as a company. And along with that, there can be lots of strategic principles, which are just... For example, we believe that being fast is more important than having features, and those are kind of pulled together.

So when you're at a company with this top-down strategy that sort of has this vision of where they want to go and this plan for how to get there, then the work that an individual product manager does, they can see how that work connects to the larger whole. And you can still have a lot of autonomy within that space. I still can have a lot of freedom to decide within this scope that I've been given, "What are the most important problems to work on, and what are the best ways to solve those problems?" But you're not just shooting in the dark. You really understand, "Here's the bigger picture of what we're trying to achieve and now I can figure out how to do my work that fits into that."

Holly Hester-Re...: Yeah. In my own career, have found that when I have that strategic structure around me, I feel so much more connected to the work and the vision.

Jackie Bavaro: Yeah, it's great for team morale. One of the reasons that vision is so important is that people like to work on something that matters. And so if you spend time investing in and create a compelling vision, it helps you recruit people to your team, but it also helps you get the most out of the people working on your team. They can be more independent because they know why they're building things. And I've also seen you work with more urgency when you're excited to get to the place you're going as opposed to seeing it as a constant stream of work with no end.

Holly Hester-Re...: Yeah. So, tell me more about growing out the team at Asana. What was that experience like?

Jackie Bavaro: Yeah. So I started as the first product manager and we'd hired one more PM before I became a manager and I actually became a manager when we hired our first user researcher. So I ended up having a user researcher report to me for a little while and then one new pm, and then eventually we consolidated product management user research underneath me, and then we ended up eventually splitting those up. So there's definitely a lot when you join a startup, that things are sort of always fluid and they don't follow a really specific plan or a way that it goes. But for me, it was really interesting as we grew the team seeing how the team changed. So originally, for example, we really hired only experienced PMs and I kind of started with... Much like nobody had taught me how to do a product management interview, we had some training internally, but I didn't feel like anybody had taught me how to be a manager or I hadn't really absorbed what's a manager's job.

So I just sort of had a sense of, "I don't want to be a micromanager, I want all the people on my team to love me, and it's just my job to hire smart people and give them the freedom to do what they want." So, we started off with very little approval process. It was just sort of, "You're smart people, here's your team, build your product however you want to build your product. You don't need to standardize and we'll do a launch review and you can definitely feel free to come in for feedback, design review, things like that. But only if you want to. We're not going to force you to. I trust you, you're smart people." And this worked pretty well until the first time that we had two PMs work on the same product surface area at the same time. So we had one product manager was working on building a premium feature that was going to be, you can upgrade if you want to get this new view in Asana. And we had another PM who was working on a visual and structural redesign UX-wise. And her redesign ended up hiding the entry point to the premium feature.

Holly Hester-Re...: Oh no.

Jackie Bavaro: Yeah. And that was when I realized that even if you have a bunch of smart people, as a manager, it's not just your job to let them run wild. You do need to help provide the structure and processes that are going to let them each run as fast as they can, but without accidentally stepping on each other's toes or running into these conflicts, that it was really my job to catch in advance and avoid.

Holly Hester-Re...: Yeah. Are you able to give us a little context on what stage the company was at when that happened? When you first started having PMs with surface area overlap, how many people worked there?

Jackie Bavaro: I feel like there probably were about three product managers at the time, maybe 30 or 40 engineers, I would say.

Holly Hester-Re...: Okay. So, what kind of structure did you start to put in place?

Jackie Bavaro: So, we started adding in a midpoint checkpoint. So, already I was sort of involved in what things were going. And that was actually a case where we added in a strategic principle. I think what we did is we reframed the goals of one of the teams. So the redesign team, their goal was maximize clarity. It was maximize clarity on a project management use case and I think it was to validate the hypothesis that maximizing clarity on the project management use case will increase user engagement. And we basically added on to that without hurting revenue. So it was just sort of like, "And one more secondary goal to pay attention to there."

But we did end up eventually adding in earlier checkpoints, especially when we had to co-launch things on mobile and desktop. And eventually we ended up at a point where we followed Double Diamond product process and we had checkpoints at sort of every key point in the Double Diamond. So you do some discovery work, and then you present your research findings. You narrow in on definition, and then you sort of present your one-page spec of what problem you want to go after. You widen exploring lots of different designs, different ways to solve the problem, maybe do some user research there, and then you sort of present early design review, and then we'll narrow in again on, "Here's the design that we actually want to build." That will get reviewed as well. And of course along with this, also the engineering parts, and then a final launch review.

Holly Hester-Re...: And who was involved in those reviews?

Jackie Bavaro: Depending on the size of the company, J. R., the co-founder who was in charge of product was always there, and I was always there and our head of design was always there, head of user research. And as the company grew, we ended up splitting into pillars. So, we decided to organize into three pillars. Each pillar had a lead and the pillar leads would show up. They had engineering design and product pillar leads, and those people would be at the reviews for all of the work in their pillar.

Holly Hester-Re...: Excellent. And how could you tell whether that new structure was working?

Jackie Bavaro: So I agonized over these product pillars, and this actually ended up being one of the driving forces for me to hire a new head of product because I felt so unsure. We knew that we needed this extra layer of organization because we couldn't have one person manage so much work at a time. And originally, I'm not sure if it was intentional or accidental, but we had some slightly weird views of management being that your people manager is there to support your growth and they're not there to necessarily be above you in the work that you're doing. And so sometimes even though we had more than one manager at this point, and I had multiple people reporting to me, the people that reported to them didn't always work in the same area as them.

So there'd be some sort of crisscrossing where some of the people that report to you, you would really understand their work, you're the one who scoped it out, it's very close to the work that you do, and some of the people are working on something that you've never seen before and that is really closer to the work that the other manager does. And people really wanted to have this more permanent organization structure and I couldn't commit. I was like, "Aah, how do you commit to one of these organizational structures?" We constantly want to be changing things around. And I reached out to a lot of people who had a product at other startups and other slightly larger companies.

And what I learned is that all of them did have some sort of organizational structure. None of them did this crisscrossing of managers to reports. And all of them claimed that it was permanent, but all of them also redid that organizational structure every year. So even though they claimed to have this organizational structure that would not change and would be permanent, in practice there was a reorg every year. And that sort of helped me realize that, "Oh, okay. I can call it permanent and I can create this structure and that will help us and doesn't actually mean that we can't revisit it a year from now."

Holly Hester-Re...: Yeah. And were you able to see in the behavior or outcomes that your direct reports achieved a difference in how things functioned once you added the structure?

Jackie Bavaro: Yes, definitely. It was a cultural change. So we needed to go from like, "Hey, your manager is just a person who's helping coach you and help you grow as much as you can," to, "No, you really need to listen to your manager. Your manager is an important reviewer and he needs to agree with the choices you've made." And we're very pro-autonomy, so managers wouldn't be giving a lot of directives, but we still needed to have that conversation and be on board. And then I think the way that we were able to scale, and not just scale doing good work, but also training people. By this point, we're trying to hire associate product managers and people who have less experience and be able to train people up because you get these more touchpoints with a manager who's closer to your work, I think, helped a bunch.

Holly Hester-Re...: Excellent. Yeah. And you recently posted an article about the three stages of the product manager career. So, I'm wondering if we can kind of take a look at that and maybe use that as a frame for what we've just talked through. What are the three stages, and when were you at them?

Jackie Bavaro: Yeah. So the three stages are shipping products, which is when being a great PM is shipping products that the [inaudible 00:27:04] customers that hit the goals. Next stage is product strategy. So, this is when in addition there's a lot of overlap. So you'll still be shipping products, but now it's up to you to start to identify new opportunities and come up with strategies to win those new opportunities. So in a way, now you're the person deciding what the goals are that you should be hitting. And it's a really interesting stage because I find that I haven't heard of any companies that's like, "Hey, now you need to start doing strategy work." Or they tend to tell you almost more as like a, "Oops, you didn't get..." This happened to me. "You didn't get promoted because you weren't strategic enough." And I'm like, "But nobody said that I was all of a sudden supposed to start doing strategy."

And so it's important to tell you like, "Yes, when you try to get to this move to senior PM or you've been a PM for three to five years, you need to start not just doing your job, but looking for those new opportunities, trying to bring in new things that you think the team should be working on, helping with the planning of what happens in the next cycle." And all of that kind of can cover individual contributor PMs. But when you move into management, usually your first beginning of management, it's still very similar. You're still just doing product strategy and shipping product work, but as you want to move into director, the job changes again. And now it's about organizational excellence. It's about building a team that can create winning strategies and ship delightful products at a scale beyond what you as a single PM could do.

It's really about multiplying. And so you don't have just one or two PMs reporting to you. You need to have a whole... Because one or two PMs probably are not going to be as effective as you as a single person who's been doing PM for 10 years could be. But you get a team of 20 PMs and now they can be delivering successful products and winning strategies at a much higher scale. And so the job is just entirely different. Now your job is recruiting. Half of your job is meeting with people and trying to convince them to join your team and coaching and developing people. So, giving people the critical and constructive feedback that's going to help them get to the next level. And about creating those processes that I mentioned so that two people don't step on each other's toes. And being a strategic leader to the rest of the company is the other half of your job.

So even though I was head of PM, half my job is being a great leader of the PM team, and the other half of my job is being in meetings with other leaders at the company with other head of design and other people, and talking over the tough problems that we were having. Not only representing product in those rooms, but just representing another smart person who cared about the company. So, that's the framework. And yeah, you have to have examples. So I think that early on in my career, I definitely was showing bits and pieces of trying to identify new opportunities. Like I mentioned, in my first years as a full-time PM I was like, "Hey, we really need Firefox support. Hey, we really need wikis." And this was sort of on the level of features. So I kind of was spotted a gap and I was like, "Go after it." And I think that's what a lot of the early strategy work can start to look like.

When I got to Google... So, this was about five years into my career as a PM was when I first heard I needed to be more strategic. And I had been just sort of sitting with my team, seeing myself as a supporter of my team, helping them launch things. And I had an idea of what we were building towards, but what I hadn't done at all is I hadn't communicated it. So in my head I kind of knew what we were doing and why, but I had never written it down.

And I wanted to learn what strategy was, so I was like, "Ask everybody," and nobody could give me an answer. And they were just like, "Oh." And I was like, "Well, who's strategic?" And they're like, "Well, that person used to be strategic, but now they're a manager, so not so much." And I felt really lost. So I did the only thing I could think of, which was take all the things I'd already thought that I had that were strategy and just write them in a document and call it Team Strategy and sent that around. And that worked. So, I think I'd been missing the communication part of it.

Holly Hester-Re...: Mm-hmm. And then your experience with the third stage, were there any interesting mistakes you made there?

Jackie Bavaro: Yeah. So, I already talked about how I'd let two people step on each other's toes. I'd say the biggest mistake I made in moving into this organizational excellence mode, and this is sort of a shift from being the best individual contributor to being the best product leader, is I love to do something and get the right answer as fast as I can. And so that's just sort of how my brain had worked my whole life. Get the A on the test, like, "Here's [inaudible 00:31:14] new product problem, here's the answer, here you go, there it is," and just zoom, zoom, zoom, zoom. And that doesn't work as an organizational leader because it turns out people hate being handed your idea. And so I had lots of processes I had sort of created and nobody knew about them, or people kind of knew about them, but they didn't believe in them, they weren't fully on board with them.

And one of the things I learned I needed to do was instead of giving people the answer, I needed to include them in the creation of the answer. So for me, it's something that's like... It's still uncomfortable because I'm like, "I know the answer. Why can't I just tell them the answer?" But you get so much better results and you're so much better of a leader if you take all of the primary sources, all of the data that you saw, the customer interviews that you saw, the things you heard from the sales team, all of the pieces, all the evidence that sort of help you form your opinion, share that with people, and then ask them the right questions, give them the right brainstorming prompts, and you will see how much of the time when given the same information as you, they'll come to the same conclusion as you. But now because they came to that conclusion, now it's their strategy, it's their process, and now they're fully on board with moving ahead with it and implementing it.

Holly Hester-Re...: That's a really great lesson that I learned as well. And sort of almost surprises me how it feels like a simple change, but it's so impactful.

Jackie Bavaro: Yeah, it's definitely weird going from being an individual contributor and having this view of what management is, and then being on the other side of it and all of a sudden understanding why your managers did all the things they were. And all of a sudden realizing, what is the balance of how much you're respected as a product leader? And how much do the people on your team want to create these things themselves? So I go through sort of a wave of feelings of like, "Oh, they should just listen to me and trust me." But then being like, "No, I hired smart people who think independently because I want them to not just trust everything I say." And it can kind of move back and forth until you start to really kind of settle into feeling comfortable with some of these management approaches.

Holly Hester-Re...: Yeah. And I know in your bio it said you're the former head of PM at Asana. So, what did you do after that?

Jackie Bavaro: So I left Asana after about eight years in 2019 and just kind of wanted to make some space, see what was going to happen next. And that's when I wrote Cracking the PM Career. And it was a lot easier... It's an idea that I had floating in my head, but I found it's very hard to write a book on career advice when you have people reporting to you. Because there's a lot of things like, "Here is the exact words you should use to your manager when you talk to them this way." And it just felt a little bit weird to be giving that advice when I had people reporting to me. And it was stuff I was telling my reports.

I was like, "Here's the template I'd like you to use with me." But it was a lot easier to sort of be totally transparent and have a different point of view doing that not as a current manager. And so worked on that book. And since then, I've been doing lots of talks, some workshops. I taught a workshop with Maven on product strategy. And now trying out different things. Not totally sure what I want to do, but also really focusing on creating this new newsletter, especially as I'm not sure how long Twitter will be a good mode of distribution.

Holly Hester-Re...: Yeah, it's interesting days for Twitter and a lot of people are moving to the newsletters. Tell me a little more about your newsletter. What's the focus?

Jackie Bavaro: So my newsletter, I think similar to both of my books, are just sort of these are all the things I wish I had known earlier in my career. These are all the things that I had to sort of learn the hard way. And I didn't have to learn them the hard way just because nobody had ever told me it. Because I had failed to read the thing that was out there because I read voraciously. I read everything that could possibly be there. I had to learn the hard way because if people talked about it, the way they talked about it just didn't resonate with me. So I really tried to focus on understanding, "What was the mistake I made in my mental model so that I can help correct that for people so that they can sort of see?" So, my most recent one talks about... I used to plan Asana's roadmap by stack ranking all of the features by priority. A lot like how you do a backlog, right? A backlog's just a type of roadmap.

And when I did this, the work at the top was always, "Build this brand-new feature." I was like, "We obviously needed this new feature. It enables a brand-new use case. Clearly that's the most important thing for us to do." And so we had a quarter of just building brand-new features. And the next quarter the designers wanted us to go back and improve those features, make small tweaks to them, make them better. And I was like, "Okay. Well, let me measure the impact or measure the ROI, the impact divided by the cost." And I was like, "Yeah, it's still enabling a brand-new use case. It's gigantic. Clearly that's higher up on the list." So another quarter, all new features. And by the third quarter, our CEO is like, "Jackie, something's wrong," and I was like, "Yeah, but the math doesn't lie."

And so I was like, "Okay, I'll look into it," and I reached out to people at other companies, which is just the main way that you learn in a startup when you're sort of... At Google, you learn from other Googlers, but at startups you learn from people at other companies. And found out that the way that a lot of other companies did their roadmaps is not a straight single stack rank of things by priority. But rather they took this portfolio approach, which is that they would say, "Well, what are our goals? One of our goals is retaining our current users and the other is winning new users. So then, do we want to invest 50/50 in these two or do we want to invest 70/30?" And you create that high-level investment philosophy before you decide to go in.

And I told it to lots and lots of people, but I didn't know what a portfolio was. I just started using the word portfolio and I didn't know what it meant. So I was like, "Well, what's another place where you do this?" And what I finally landed on was a charcuterie board, because on a charcuterie board, you don't say, "What are my 10 favorite foods?," and then just stick them on the board. Instead, usually you want some meats and some cheeses and some fruits. And so you have some high-level view of how you want to split those up, and then you can pick the best from within each group.

Holly Hester-Re...: Yeah, that's a really great analogy. I can see how you're taking the time to think about the mental models and how they need to shift. So, I think we're coming up on the end. How can people find you if they want to follow you?

Jackie Bavaro: So, I'm active on Twitter. So, @jackiebo. And then also, yeah, on my Substack is probably the best place now. So jackiebavaro.substack.com.

Holly Hester-Re...: Awesome. All right. Well, thank you so much for your time today. It's been a pleasure talking to you.

Jackie Bavaro: Yeah, thanks for having me.

Holly Hester-Re...: The Product Science Podcast is brought to you by H2R Product Science. We teach startup founders and product leaders how to use the Product Science method to discover the strongest product opportunities and lay the foundations for high-growth products, teams, and businesses. Learn more at h2rproductscience.com. Enjoying this episode? Don't forget to subscribe so you don't miss next week's episode. I also encourage you to visit us at productsciencepodcast.com to sign up for more information and resources from me and our guests. If you like the show, a rating and review would be greatly appreciated. Thank you.

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