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16 Jun 2022 Lenny's Podcast 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

“pen our office. So I really felt like, I was getting a lot of personal growth and I was getting an opportunity to learn things that I wouldn't have that opportunity anywhere else because of my sort of background and my deep like knowledge of this product that I was able to be exposed to this and have these responsibilities.”

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Speaker unverified
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evaluation
Recorded
16 Jun 2022
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Lenny's Podcast

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

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