Season 6 - Episode 2

Breaking Down the Product Career Ladder

Jackie Bavaro is the former head of product at Asana and the co-author of “Cracking the PM Interview” and “Cracking the PM Career”. Jackie has coached, mentored, managed, and advised hundreds of people in product and people who aspire to move to product roles. In this podcast, Jackie walked us through what a career in product looks like, secrets to succeeding as a PM, and her mission to level the playing ground for product people around the world.

Tell us about your thought process from the original book Cracking the PM Interview to now Cracking the PM Career?

Both this book and my original book had a lot in common. So Cracking the PM Interview was inspired by my experience of seeing that when I applied to be a PM, I had gotten rejected my first time applying to Google, made it in a year later, and then I interviewed hundreds of people. And while I interviewed them, I realized that some of the reasons people pass or failed the interview weren’t directly related to their skills and how good of a PM they really could be but were more related to how well they had prepared for the interview and how much structure they added to their answers.

I thought that if we want to have more great PMs in the world, we should really level the playing field. And any advice I’d be willing to tell a friend of a friend that I should be willing to tell anybody on the internet or anybody in the world who wants to buy the book to really make it possible so that everybody has a good chance to become a PM. I would say my idea, but now it’s sort of the sequel, let’s say, you’ve got the job now, how do you succeed as a PM? And how do you advance in your career? And just like I saw, there were some sort of hidden secrets to the PM interviews. I found that there are also some sort of hidden secrets to succeeding as a PM. There are some tips and tricks that if you just understood them a little bit better, you could get on the right path. You could build products that did better in the marketplace. And you would be able to work better with your manager and with your cross-functional partners and advance so that you can get all the recognition that you deserve.

Tell us about your life before being a PM and then your career as a PM.

Yeah. So I studied computer science and econ in undergrad, and I’m one of those lucky people who got to go straight into product management. So I became an intern at Microsoft,  after my sophomore year of college and I loved Microsoft, so I decided to go work there, full-time for about three years. When I was moving to New York,  Microsoft didn’t have any PM jobs there and I loved product so much and wanted to do that. So I applied to Google. That’s when I got rejected, the first time decided to stay with Microsoft as a Microsoft consultant for a little while, and then switched over a year later to become a PM at Google. I loved Google, stayed there for three years. 

One day I got a message from a friend I knew from Microsoft saying, Hey, I’m at this new company, do you wanna have a coffee and learn about it? And I was like, well, what harm would a coffee do? And that’s how I ended up as the first PM at Asana. Asana was an amazing experience. I started as the first PM, became head of product management, and grew the team to be over 20 people. So during that time I got to become a manager, have all these experiences I got to write my own career ladder is to try to help coach people on my own team to grow and, and absolutely loved it. And then about a year, a little over a year ago, I decided it was time for something new. And that’s when I left and I’ve been working on the book and handling the pandemic and a preschooler at that time, too.

What are some of those parallels between building something physical and building something deep?

Yeah, so I think, the thing that they have most in common is that in both cases you should really have a goal, and you have to sort of understand why you are building this product? What problem is it solving? Why, and what will success look like? And the exact same thing for a buck is why do you want to write this book? What problem is it solving? And what will success look like? I’d say that some of the biggest difference though for me is that as a product manager, everything you do as a product manager, you get done through other people, you really work to influence the people around you influence the designers, influence the engineers, and at the end of the day, you’re not the person who’s sitting there typing the code. So with a book, you’d get this difference, which is that you actually have created something tangible with your own hands at the end of the day, which, a nice break from the sometimes thankless job of product management.

How did you structure your book? Because I can imagine there are so many different ways you can grow your PM career.

The way that we’ve structured the book is that the first chapters are on the product skills. What I did is I talked to lots of product leaders, lots of different companies looked at the job ladders. And what I found is that the job ladders looked very different from company to company. Every company groups the skills together differently. But if you pull apart those groupings and look at what skills are underneath the groups, they’re very consistent from company to company. So I grouped them as product execution, strategy, and leadership. but there are lots of correct ways. There’s no one right way to group them. So for example, is communication a leadership skill or a strategic skill? You can move them around, but in all, the product skill is data insight is that strategic or product.

The skills were very common. So we go over those, break it down into many, probably more than 30 sub-skills here. That’s the first chapter of the book. We have a whole section on people management and what it takes to move into people management and the new skills you need when you’re there. And then at the end of the book, we really talk about career paths and career ladders. So the skills are the individual practices and frameworks, and responsibilities you need to really succeed at your job. But when you want to translate being good at your job into getting promotions, it’s not a one-to-one match between skills and being good at your job. What I mean by that is you might have the best possible user insight and data insight, but if you can’t use those insights to ship great products that help people and solve problems, then you’re not really having the impact that you want to have. And then you won’t be getting those promotions and you won’t be advancing. So at the end of the book, we really talk about what, what does the career ladder looks like? What differentiates an APM from a PM, one from a senior PM, from a PM lead, and a director all the way up to head of product. Then we’ve done interviews with a lot of successful PMs and talked about their paths and what they’ve learned along the way.

How would you describe like the different career ladders?

What I’ve learned through this research is that there are three phases to a PM’s career. So the first phase is the PM phase and that’s when you’re focused on shipping products. When you think about your PM interviews, and what you may be doing for your first five years as being a product manager, it’s really all about shipping great products. It’s all about, researching, researching the customers, validating your designs, maybe running AP tests, analyzing them, iterating, improving, and shipping things that are successful. You get better and better and better at that. But to get to senior PM, there’s actually the role, the role changes. And you don’t get to be a senior PM by just becoming better at shipping products.

You get to senior PM by getting better at product strategy. So that means not just how do we take this product and ship it really well, but what products should we be building? What goals should we be going after? What should we set our roadmap? What’s our long-term vision? How do you set a long-term plan that will help your company win in the marketplace? That’s a new set of skills and a new set of work that you do as a senior PM that as an APM, you might not have even realized existed. And it’s sort of interesting as a new PM. When you look at the senior PMs on your team, you might wonder like, Oh, what makes them a senior PM? I don’t see what they’re doing. That’s so great. And that’s because a lot of it is behind the scenes. A lot of that is going to be strategic work. They’re doing the strategy. They’re creating the times that they go to an executive and they convince them too that we need to hire people who know AI so that it can be ready for the moves we’re going to need to make two years from now. So you get better and better at product strategy by deciding what your company needs to do to win in the marketplace. And they say, great, I’ve reached the top. There’s nothing else to learn. 

But it shifts again, and there’s the third phase of product careers, which is organizational excellence. So once you move into people management, the focus now is not on shipping great products or creating product strategy, but instead on building a high performing team that can create good strategies and ship good products. So now the role really becomes about hiring people and coaching and developing people, setting up processes, helping different departments at the company, work well together, removing obstacles,, finding these, these huge multipliers on your team success that will help the whole company succeed, even though, without your having your fingers in, on every little product decision. 

What’s interesting, as some heads of product will still be very involved in product review and making those small tweaks. And so as an APM, let’s say, when you think of what your head of product does, you might think that most of their job is this feedback you’re getting in product review. That most of the job is the way that they like, knowing exactly how the design should work or that kind of thing, but that’s really a small part of their job. And the larger part of the job is building the team and coaching the rest of the company on company strategy.

Some PMs enjoy being at the front line with engineers designers, and they may not want to become the head of product and build teams, but they still want to grow in their careers. What is your take on that type of career path?

What I found is that a lot of job ladders have some level at which it’s okay. One is that there’s some level at which it’s okay to not continue advancing. So for example, most companies will not let you just hang out as APM for 10 years. If you’re on your eighth as APM and you haven’t graduated to be a PM one, they’re gonna say, Hey great work, but like, I’d rather have that headcount spot for someone who’s going to be growing faster. It’s really meant to be a training job that you hire people and, and grow them. But for most companies, senior PM is around the level where if you’re a senior PM, you’re a high-performing member of the team you’re independent.

You create a lot of value on your own. And for example, if the work-life balance is more important to you at this point in your career, if you have a side project that you’re really passionate about, you could spend your entire career as a senior PM, and the company would be really happy to have you, and you don’t need to continue to get promoted, to stay at a company. Career success can mean so many different things to different people that that’s an entirely valid approach to your career. I think that, if you make it that far, you should be very proud of what you’ve done and you shouldn’t feel extra pressure to just take on new responsibilities.

Then there is the principal PM role. So the title between senior PM and principal PM can vary from company to company, but generally what distinguishes a principal PM is that they are an expert in their industry. So they’re not just the best in their company at something, but actually, they’re well-respected in the industry at having been the, being the person, the go-to person in the industry to understand the concept. Another part about becoming a principal PM, you need to join a company that has a business need for a principal PM. So that means they have a business need for somebody who is so advanced, so strategic, so excellent at product skills, execution skills, product strategy, and that the size of the work that they need to be responsible for, to create a large impact that justifies their high salary. But that can be done with a small enough number of engineers, that you don’t need to be a people manager. So in product careers, a lot of times people become people managers because it’s going to take 50 engineers to build your product. And one PM can’t lead that many engineers. Some places where principal PMs are very valued are for example, in high-stakes partnerships. So for example, if Yahoo and Microsoft are partnering on something, that’s the kind of place where you really want a principal PM because the actual amount of product work is small enough for you engineers to handle, but you really can’t afford anything going wrong.

What are your thoughts about different kinds of PM structures as the product evolves?

The future of product I think, is really going to be that there’s going to be a lot more product managers. And not every company, especially small ones can’t afford to have an extra person who only does product management. So I really think that people from many different roles are going to start learning and picking up PM breast practices. These kinds of product best practices, like, think about your goals before you start the work. It’s kind of obvious, but that’s the sort of thing that product managers are really trained in. I think we’ll start seeing lots and lots of roles that can benefit from that mindset.

In the PM career ladder, what is the kind of like the ultimate step?

I think there are lots of different directions. So I think if you were going to go with a normal straight career ladder, I would say probably head of product which becomes not just, being responsible for product managers, but also designers and researchers, and depending on the company engineers, or they could be separate. But that’s really just the traditional path. I see a lot of people choose other careers after product management. For example, one really interesting role as general manager. So I mentioned the head of product might be responsible for the PM’s designers, maybe the engineers, general manager of a business unit is responsible for those people within a department, but also, the sales and the marketing people, all of the different departments together. They’re really considering both the profits and the losses and everything it takes to bring a product to market successfully. So that’s one of the general managers. People also tend to go into various roles in venture consulting. I see people move into product coaching. Some people move into a chief of staff roles, although that’s a title with an even more ambiguous title than a product manager. So there’s, what’s very junior and very senior chief of staff roles. So there’s a lot, there’s a lot of different things that can be set up for it. And then, of course, CEO role CEO roles and founder roles,

How did you learn the skills to truly become a product leader?

There’s one framework that I was reflecting on for the book that I put together that I really like, which I call notice, assess and improve. What I found is that, so I think the best way to improve as a PM is to get feedback, and especially feedback from your peers, feedback from your managers, and also feedback from your manager, peers. So if you’re at a larger company, for example, the other PM managers are a great source of feedback. A lot of the time, the feedback that you’ll hear as a PM, isn’t very actionable or doesn’t seem actionable at first. So you might hear like, you need to be more strategic, or you need to be more on top of problems on your team, or you need to not let the date slip or whatever it is that you hear.

When you first hear it, maybe it doesn’t resonate with you. And you’re like that doesn’t like it. And sometimes you’re like, you’re wrong. Like, no, you misunderstood the certain situation entirely. And that feedback is unfair and invalid. But if you split it up into notice, assess and improve, what you can say is first, notice means find the situations where this feat, where this feedback might be applicable. like what are the cases where, the person giving you feedback thinks that you had a problem here, what’s the pattern. And, and that very first step, when you start to look at the pattern, a bunch of you might see a bunch of different things. One of these might be that you, you didn’t even notice these situations. So maybe somebody says you have a lot of miscommunication. And you’re like, what?

And they’re like, well, in that last meeting, and you were like, what? So the first step there might just be learning to be like, okay, can you please just like give me a signal, you know, touch your ear every time, I have a miscommunication or cut your ear, or every time I interrupt someone or whatever it is, the skill that you’re trying to notice. So first just gather this large bank of examples, and training, training yourself to notice these situations. Then the second step is to assess. So one thing that might happen is maybe you were noticing all the time that, for example, that your project was late, or that your, your dates kept slipping maybe, or maybe you were very aware of that, but they thought that they just slipped because he made a mistake, but actually you had made a really intentional decision to move the date in each of these cases.

And so something went wrong cause they, they weren’t happy with how it went, but the problem that they named might be a little bit different than the way that you want to frame the problem to work on it. So maybe the problem from your point of view, isn’t that the date slip, the problem is that you didn’t loop in the stakeholders when we’re moving the date and you didn’t buy-in enough and you didn’t persuade people about the date. So there, you might say that the problem wasn’t your judgment, or your execution skills on getting your team to ship as fast as possible. The problem was really the communication skills. So when you’re able to reframe, go back to the person who gave you the feedback, double check it back could be true, and then you can work on that final step of how do I improve? How do I like to set up what I want to do, set a goal, practice it, and then go back and check with someone that improved and sort of a long way of saying how I think you can kind of make the most out of the feedback we’re getting. So you can advance as fast as possible and improve your skills as fast as well.

What are your thoughts on mentorship?

So I think that mentoring is very important, for two reasons. One is that I do have aspirations to be a people manager than mentoring is a prerequisite. Is that being a mentor is how you demonstrate those skills and build that trust that you’d be a good product leader, but even if you have no interest in people management, mentoring is how you can give back to the community. Especially because we are, we’re still in the very early days of product management as a career, you’re able to have a very large impact on the world and across companies, if you are able to help mentor other people, one thing I’ve learned is that people are very, are interested in different types of mentorship. So some people really like one-on-one mentoring with someone, some people like to get groups together.

Some people like to put together a big presentation of what they’ve learned and take it on the conference circuit. Some people like to tweet, some people write to like blog articles and so if you’re looking for a way to give back to the community and to mentor people, what I would say is that you don’t need to fight your personality. It’s okay to pick the approach that really calls to you. The one that feels like less work to you, the one that you are doing the most, and use that to go forward. If you are doing the writing, the thing that I think that the community needs a lot more of is stories about real product management. So if anybody out there who’s listening and wants to, wants to contribute, I think that there was so much value that even a fairly new PM can have, if you just tell the story about a product decision you made and how you thought about the choices, the interesting things you learned and how it turned out, and maybe what you learned, after that and how you would’ve done it differently.

I think that each of those stories is valuable, and there’s no chance of the world being too filled with that stories. Everybody will love to learn those specific ones and it’s, and you really are the expert on your story. And you can kind of work with your company to make sure that you’re not giving away any secrets that they don’t want you to.

What is your goal with this book?

You can pre-order Cracking the PM career on Amazon now, and we are working on the layout for the Kindle version. In terms of the goal for the book, it’s a few different goals we have, but one of the ones, so high level my goal for the book is to create more great product managers in the world, because I want there to be more good products in the world. And every time I see a product that has a terrible UI, you know, I feel I’m like, Oh, I wish I had a better product manager there. Also there are these products where the entire product and the thousands of hours people put into it fails as being like quippy recently. And so many people put so much effort and so much energy and so much love into that product. Some of the premise was flawed from the start and better product management. I think I could’ve prevented that waste of energy.

I’m hoping that through the book that more people improve their PM skills, that we create better products. And again, I’m really hoping to level the playing field so that the people who are really skilled into the people that are the best at their careers are able to get a fair shot at expanding their scope and their impact and getting the promotions they want so that they’re able to have as much influence as they deserve.

How is this product management discipline going to evolve?

To touch on agile for a second. What role does project management happen in product management? And I think what I found is that product managers spend so long being like I’m a product manager and not a project manager that then when it comes time to do some project management at your team, you’re like, no, I can’t do it. It’s not my job. But to have your team be successful and be able to ship products, you do need to do some project management. And, what I learned is that almost every current software team is agile-ish. The agile frameworks have a lot of good stuff in there.

The idea of doing daily stand-ups, the idea of doing sprint kickoffs and sprint retrospectives. But you don’t need it all. You don’t need to do it in a very formal way. A lot of times, if you are having trouble with project management, taking a look back at the agile concept, sometimes there’s just one that will help. A lot of it lets a team be sort of self-lead and prevents a PM from having to be, having to be the one, pushing everyone and like putting the pressure on instead the team can put pressure on themselves, which ends up leading to better functioning. 

In terms of how product management will change in the next 10 years. So first of all, I think there’ll be a lot more product managers. I think a lot of people in jobs that aren’t official product managers will be using PM best practices.

The biggest change I think I’ve seen from, I think back to 10 years ago is how easy it is to do A/B testing now is that 10 years ago things shipped software shipped in a box and you just didn’t get very much feedback and iteration on how what you built did. So if I’m going to carry that forward, I’m hoping for that in the next 10 years there will be improvements in rapid prototyping and especially, today, it’s now becoming really fast to create like a quick click-through demo or a click-through mocks. One of the places I think we’re maybe going to see soon, we’ll be connecting really cheap, no code front ends to the real customer data backends. Because that will let you do AB testing doing much more advanced types of AB testing before you’ve built out the full, scalable productized version of your code and that lets you validate your ideas sooner and that will let you get past the bad ideas so you can find a good idea faster.

I’ve always been a proponent for a while that I don’t think you need a computer science background to be a good PM. And I think that we will see more and more of that as you need less coding skill to be able to self-serve that as a PM, you’ll be able to get your own data. You’ll be able to run your own A/B tests without having that computer background. You still need to know about computer fraud.

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