How do you get your foot in the PM door? Read the full transcript of our chat with Jackie Bavaro, product advisor at Asana and co-author of Cracking the PM Interview

Eric Boduch: Okay, welcome lovers of product, I’m here today with Jackie Bavaro from Asana. Jackie, why don’t we kick this off by you giving us a little overview of your background?

Jackie Bavaro: Nice, so thanks for having me and just a little bit of my background is I started product management right out of college and I went to … I studied computer science and economics at Cornell for undergrad and then went straight into being a PM at Microsoft. I got to be there for three years and moved over to the Google APM program, where I got to work on Google Search, which was a lot of fun, got to work on a really broad consumer product. Then moved over to Asana, where I’ve been for the past seven years. At Asana, I started as the first product manager and grew to lead the PM team and in the middle of that, I had a great experience where I started a blog that grew into a book and so I got to co-author Cracking the PM Interview.

Eric Boduch: That’s awesome. Talk to me a little about the writing process.

Jackie Bavaro: Nice, so I started writing because when I was at Google, I started having friends of friends say, “Hey, I’m going to be applying to the Google PM job, can you tell me a bit about it before I start getting there?” So I would meet with these friends and give them a little bit of advice and help coach them and I started to realize that this is how a lot of people are getting their APM jobs. A lot of people are getting this one on one coaching because they have a friend of a friend who worked at Google and that that is a very biased way to figure out who gets to know what are the tips and tricks to get these jobs. So I wanted to say that if there’s anything I’m willing to tell a friend of a friend, I should also be willing to put that out on the internet and willing to make that public.

Jackie Bavaro: So I just started with taking these conversations that I was having and distilling the key points and putting them up on a blog. So that’s kind of how it all got started.

Eric Boduch: That’s awesome, we’ll get back to the book and hiring in general in a minute but let’s talk a little bit more about Asana. Really interesting company, seems to have a huge focus on culture, at least that’s my understanding, employee culture in particular. Talk to me about that.

Jackie Bavaro: Yeah, so Asana’s a very mission-driven company. Our mission is to help humanity thrive by enabling all teams to work together effortlessly and so our culture is really just one of the ways that we think is best to achieve that mission. So at Asana, the way that I would describe our culture is that we’re very mindful and reflective. So that means that we’re always willing to iterate on our culture and we treat our culture as a product. So some of the ways that manifests is at the end of sprints, we’ll do retrospectives and across the company, if something goes very badly, so for example if there’s a site outage, but also if somebody leaves the company who we didn’t want them to leave, or if there’s a big blow-up on the marketing side of things, we’ll do this five whys process where you keep asking why to get deeper and deeper in.

Jackie Bavaro: Then we’ll figure out what are some appropriate next steps to do to take it to make it less likely to happen in the future.

Eric Boduch: So talk to me a little bit about that iteration process. Can you give an example of that?

Jackie Bavaro: Yeah, so I think one of the things that stands out the most to me in terms of how our culture is iterated as been how we treat due dates and deadlines. Is when we joined the company, we had a very eng-heavy culture, where deadlines were sort of taboo. In fact, it came across in our product, because we had a due date field that we had added because customers asked for it, but it didn’t do anything. You couldn’t get notified when a due date was coming up, you couldn’t even sort by due date.

Jackie Bavaro: So at the company, we sort of had this idea that due dates were bad and people who manage by due dates were just trying to force engineers to deliver stuff on unrealistic deadlines. But as we grew, we started to see the benefits of due dates and deadlines. We started to see that hen you make a plan and you set some dates and you make some estimates, if you miss those, that’s a sign that if you do that reflection and learn how can I do better? How can I move faster in the future?

Jackie Bavaro: So we started to get a little bit more into due dates and deadlines and I would say that originally we over-corrected, so we had a time where every week we would all get up around a shared company calendar and everybody would talk about their milestones in front of the whole company and talk about any milestones missed, in front of the entire company. So that started to veer a little bit too much towards a heavy emphasis on deadlines.

Eric Boduch: I can see that.

Jackie Bavaro: Then we have sort of brought it back into a really nice, healthy middle, where we do a lot of road-mapping and we set quarterly goals and we’ll pay attention to these dates and we will do the analysis but we make sure that the motivation comes more from the inside the team, rather than externally.

Eric Boduch: That’s cool. So you talked a lot about having a mission-driven company, or you just mentioned having a mission-driven company and that’s something I want to touch on in this question because there’s got to be implications to having a product team, or to your product team actually, having very product-focused founders with a mission-driven company to boot, right?

Jackie Bavaro: Yeah.

Eric Boduch: What are those implications?

Jackie Bavaro: Yeah, so I think it’s really wonderful to work at a mission-driven company. The main reason is that it feels like every person at the company is on the same team and I’ve worked at, like I said, both Microsoft and Google before, both really large companies and both kind of known for not always having the best inter-team relationships. Whereas at Asana, we have a lot of cohesion across teams and not just across different product teams, but with the sales organization, with customer support, because if there’s ever a disagreement, we can always take it up a level if we have to, get all the way to like, “Okay, we’re both here to work on the same mission, right? Let’s figure out why we disagree, what’s going to happen.” So one of the things that it lets you do is it makes it really easy to take off your team hat and put on your Asana hat.

Eric Boduch: Interesting. So what about the product side of that? As a product team, your founder’s very product-focused, right?

Jackie Bavaro: Mm-hmm. 

Eric Boduch: How has that affected your product team too?

Jackie Bavaro: Yeah, it’s wonderful. So yeah, Asana has a very strong mission and a very strong vision and so a mission is sort of like what goal we want to achieve and a vision is an idea of, what will it look like when we achieve this? That’s really important because it gives us a North Star to aim for and it helps us understand what could success looks like and how far away is it? How big are the steps we need to take to get to that future world?

Jackie Bavaro: One of the biggest problems I see with product teams is incrementalism. Is when teams get really excited about polishing and iterating on the most recent thing they built and making it a little bit better and a little bit better and a little bit better but not taking it these giant leaps that will actually have an impact on people’s lives.

Eric Boduch: I mean, I think there’s got to be a balance there because if the people are still getting positive outcomes, you can see better performance, better scalability, better this and they’re still making results but at the same time, those are resources that maybe could be applied to something that was earth-shattering, so to speak, right?

Jackie Bavaro: Yes and I think it’s good to think about it as a balance of how much time do you want to spend polishing the work that you currently have and how much time do you want to spend investing in new big bets?

Eric Boduch: Awesome. So let’s talk about what you mentioned earlier, which is Cracking the PM Interview. What have you learned since you wrote the book? What feedback have you gotten since then?

Jackie Bavaro: Yeah, so I wrote the book four or five years ago and one of the most surprising things to me has been that it’s gotten more popular over time. Product management as a field is really heating up. There’s a lot more people who are interested in product management and a lot of people who are either getting into it from new grad, or from transferring into the field. But I would say that one of the things is kind of surprising is how much the interview practices actually haven’t changed massively. A lot of the advice that is in that book, people have said is still entirely applicable today. So I think that there’s a lot of … I guess maybe the most surprising thing, is that people who interview PMs for jobs, so people who are already PMs and are interviewing people to join their team, have used to book to get guidance for like, “Oh I never knew how to think about what skills I should be looking for.” So they’ve been able to use it to help improve their recruiting process.

Eric Boduch: So one thing we talk about a lot is homework assignments for PM interviews, what do you think about that?

Jackie Bavaro: Yeah, so I think it’s … I’m pro homework assignment but I think it’s a really delicate balance. I think that as a company when you’re interviewing people, you have to be careful about how much free labor you’re asking for and especially for people who might not have that much time or people who are more senior in their career. They might be less willing to do a homework assignment, so …

Eric Boduch: Would you ever pay them for the time?

Jackie Bavaro: The way that we have done it at our company is we use it early in the process, and so we will, for more senior people, sometimes skip that step. When we’re interviewing, yeah, for much more senior roles, we’ll sometimes do that as a phone interview instead. One of the real benefits of having that homework assignment is that it is a much more scalable way to interview candidates. It gives you a really strong signal. We’d say that the signal we got from the homework assignment is much stronger than the phone interview signal we’ve gotten and because it’s so scalable, we have a rubric and we can grade them really quickly, it lets us open the top of the funnel more broadly and lets us interview candidates with less traditional backgrounds that otherwise might have gotten filtered out at the resume screening stage.

Jackie Bavaro: So I think that the homework assignment can be a tool that you can use to increase diversity in your pipeline.

Eric Boduch: I like that a lot because I think people coming from a lot of diverse backgrounds can add a lot to product teams and by getting the homework assignment early, you’re not … I guess you’re avoiding some of that unconscious bias that might come out of the phone interview based upon your experience? Is that accurate?

Jackie Bavaro: Yeah, we try to look at the homework assignments in an anonymous way, sometimes they’ll put their names on it, so you can’t always keep it totally anonymous, but we try to grade in an anonymous way and have a set rubric. So it’s obviously a little bit hard to … with a homework assignment for a PM, with PM information, there’s no one right answer, but we try to make it as fair as possible, to be able to recognize talent from all kinds of people.

Eric Boduch: Okay, let’s twist that around. Now, what advice would you give to product managers who are interviewing? How should they assess what product management was like at the company they’re interviewing-

Eric Boduch: Ask what product management was like at the company they’re interviewing and if it’s going to be a fit for them.

Jackie Bavaro: So I think that one of the most important things is when you’re joining a new job is just the team. Really getting to know the different people, so they seem like people you can learn a lot from. Do their processes seem like they are at the level you want? One of the things I notice is there’s a tipping point in people’s careers when you go from wanting the career where you’ll get as much mentorship as possible to wanting the career where you get to mentor other people, and you get to have a little bit more autonomy. So double-checking to see if the job you’re going for has the right match for you in terms of being the mentor versus getting mentored relationship.

Jackie Bavaro: And then I would check in on the relationship of product to the rest of the organization. One of the things I love about Asana is we have a really healthy product organization where engineers like their PM’s. They’re excited when they get a PM on their team. And I know a lot of companies aren’t like that. There are ones where’s there’s tension between PMs and other teams, or tensions between senior leadership at the company. And those things can make it really hard to be effective as a PM.

Eric Boduch: It’s interesting that you mention that. We did a study with Product Collective, the people who put on Industry, and one of the things we looked at was the amount of influence and connection between PMs and other departments, and engineering as a whole. The connection, the influence is really low. Would you have expected that?

Jackie Bavaro: That the PM’s had very low influence?

Eric Boduch: Very little connection. There’s like a wall in some ways

Jackie Bavaro: Oh that’s very surprising. As a PM one of the best things you can do is form those connections across a company, especially at a big company. It’s one of the reasons I think that a lot of companies love their APM programs for new grads or more junior PMs. It’s that PMs will form relationships that are far away in the company and a lot of times things get done through the APM network where two senior PM’s may not know anybody on the other team, but the APM’s are like, “Oh I’ve got a friend over there, I’ll just ask them for some help.”

Eric Boduch: Yeah, I mean, I just pulled up that information. “Product teams reported they had poor alignment and influence with engineering teams. In fact, they had better alignment and influence with service and support, revenue marketing, design and UX, market research, customer success, brand, product.” Shocking, right?

Jackie Bavaro: Yeah.

Eric Boduch: I was thinking they just need to get together more. Have coffees, have a little beer, more together, get that integrated. But it sounds like Asana does not have that problem at all.

Jackie Bavaro: I think that we don’t have it as a systemic problem, but I do think it’s really important and we have some really nice onboarding flows that we send people through. And one of them is to have a new hire have coffee with and have coffee chats with all the people on their team, and with several key people across the company. And even some suggested topics there where you’re new to a team and you talk to engineers and you say, “Hey what drives you, what motivates you, what are you excited about, what have you loved about working with PM’s in the past, what are you hoping for in the future? Do you have any pet peeves.” I love when you’re kicking off with a new team, it’s such a good opportunity to get things started on the right foot.

Eric Boduch: Talk to me about something you wrote, this concept of product sense. What it is, how to grow it?

Jackie Bavaro: So yeah. Product sense is a thing if you’re looking to become a PM, or looking to grow as a PM, you’ll hear a lot of people talk about. They’ll say, “Oh you need to have better product judgment,” or “There’s just this spidey sense PMs have.” And it is a really important skill, but also it’s something that you can build. It really is just the accumulation of all of the intuition you build up after all of these experiences with launching products, getting them out there, and then seeing what the reaction is. And being able to problem solve and innovate to get clever solutions to product problems.

Jackie Bavaro: The first key to this is customer focus. And there are so many different ways to get to know the customer. Some of them are by directly talking to the customer, some of them are by looking at data, and analytics and metrics to understand how customers behave. And also to be able to follow through on the launches you have. To be able to launch and iterate, and read that feedback and understand how the choice you made early on impacts things later on.

Jackie Bavaro: Another thing you can do to develop that product sense is to use a lot of products. One of my favorite things that PMs do and one of the best kinds of innovations I see is when a PM cross=applies a product pattern they’ve seen in an app to a different domain. So people may use a metaphor or a UI paradigm that you use in a music app and start using that on a mapping app, or some other kinds of cross-pollination. And those often serve as really good ideas.

Eric Boduch: It gets to Uber for hairdressers.

Jackie Bavaro: Yeah.

Eric Boduch: I don’t know. I just made that up on the spot.

Jackie Bavaro: Well there’s the big set of what the product actually is, but even on a narrow set you might say, “Oh I love the search interface that Spotify is using.”

Eric Boduch: This is like we’re going to apply Spotify’s search interface to finding hairdressers, whatever it happens to be.

Jackie Bavaro: Yeah.

Eric Boduch: Interesting. I like that. What else? I think you mentioned things like doing product teardowns and setting up goal practice.

Jackie Bavaro: Oh yes. One way to get used to product is to actually use a lot of products.

Another is to do a product teardown where you can get a few people together and actually just think about bit by bit look into exactly what the product is, and the choices they’ve made, and analyze what they’ve done that is working well and not working well. And try to understand why they might have made the choices that they did. And we do those on a regular basis at Asana, and we’ll actually be able to pull it apart and see what are the clever things they’ve done, what do we guess about their customers based on how they do this, and it’s just this sense of trying to get how do you get in your ten thousand hours of practice as a PM.

Jackie Bavaro: Goal practice. I wrote this article a little while ago. Sorry, I don’t remember the full details of that one.

Eric Boduch: That’s okay. I find it really interesting because I talk a lot with young PMs and they’re like, “Oh how do I get started” and they’re like, “How do I find a job to get started.” And it’s like you don’t really need the job to get started. Pick a product and figure out how’d you run it, and write it up, and talk about what’s good and bad, and then run it by some of your friends that might be in PM, or some mentors you know, and get feedback from them. Or offer to help a startup on the side. There are lots of ways you can get involved.

Eric Boduch: What I really liked about this article, this product sense article, is you’re giving people ways they can train themselves. It was like cross-training for product managers or cross-fit for product managers. Let’s do these goal practices. You can write down all the goals you can think of the product. You can think about who built the product, and who purchases and uses it, and what PR material could be. And you’re in essence, you’re becoming a little mini product manager for that. That was really cool, I like that approach.

Jackie Bavaro: Great. I definitely think product management is something you can practice and you can get better at. It’s not that people need to be born as a product manager. One of the things you said actually reminded me of people often ask, “How do I break into product management?” And the number one way to break into product management is to start doing product management inside the job that you are currently in and find a way to transfer within your company. There are lots of ways that people do become product managers. Some people were PMs and get hired as the first PM somewhere else. But that’s much rarer. Some people do go to business school and then you get hired straight as a product manager, but that’s two years of your life.

Jackie Bavaro: Many people, the most common way I find that people successfully transfer into product management is whatever their job happens to be, they just start picking up and doing some product manager type stuff. Maybe they’re and eng manager and they start planning out the road map and thinking about strategy. Or maybe they are on the customer support team and they start writing up some specs about how the product could be better to avoid all these customer support tickets that they have to keep answering. Once they get to picking up some of this stuff on the side, those people can eventually work with their boss to get their job title switched over to product manager. Sometimes spin up a new product management org within their company, or transfer into the role.

Eric Boduch: Yeah, I agree. I hear that more often than anything else. It’s like, “I was in this job, I was a dev manager, I’m even in sales engineering, but I spent more and more time with the product team, and they have little projects that I can help with, and get some mentorship, and eventually there’s an opening. Kind of worked my way over there.” Which I think is a great way to do it, which shows they have the curiosity and the passion to do it too. It’s almost self-selecting, right?

Jackie Bavaro: Yeah. And one of the most important things as a product manager is credibility. And you’ve already built up a good reputation at your company, you already have that credibility and so that really eases the transition into product management.

Eric Boduch: One thing you were talking about today, and we’re at the Industry conference, so this will be published a little bit in the future, but you were talking about roadmaps. And you do something called roadmap week, right? Talk to me about that.

Jackie Bavaro: Nice. At Asana we do something we call roadmap week, and we do it once an episode, which right now is twice a year, but originally our episodes have been different lengths of time depending on our themes. The company started roadmap week because before that they found that they were constantly doing planning, and it was a constant state of planning that never ended and would interfere with the product work. And they realized that by separating out the planning into a fixed week when everybody would expect to have lots of meetings and not be getting too much straight-up engineering work done, we could consolidate the planning into one week, do a bunch of planning and then execute on those plans as fast as we could in the following weeks.

Jackie Bavaro: As that’s grown, we’ve built to continue having this roadmap week which is a nice checkpoint that lets us reflect on what’s happened in the past, plan for the future, and because everybody clears their calendar for the same week, it lets us bring all of the right people together into the conversations.

Eric Boduch: What else about roadmaps? If you go from one product org to another, there are lots of different ways people approach roadmaps. Do you have any tips or tricks? I hate to use the word tricks. But tips, advice.

Jackie Bavaro: Yeah. Definitely. From my point of view, your roadmap is your plan for how you’re going to achieve your vision. And the key purposes of a roadmap are to make sure that you’re taking big enough steps in the right direction to achieve that vision. So if you have this amazing vision and you look at the size of the steps you’re taking now and you’re like, “Oh it’ll take us seven years to achieve our vision,” you might decide that you need to do something more drastic now.

Jackie Bavaro: The second point of roadmaps is to create alignment across the company. And that alignment has a lot of benefits, it can motivate the people on your team, you get excited to work fast to get to the next thing, it helps people across the company plan for what’s going on in the product side. So, for example, we will often find that if we have product launches coming up, we definitely need a lot of marketing time to build up the marketing materials, and we might even need to start hiring ahead on sales because we might be selling to a new type of customer with this launch. So being able to coordinate across the company is really important.

Jackie Bavaro: My number one question that I get on roadmaps is, “How do you prioritize when things are apples and oranges?” My tip here is you don’t need to choose between apples and oranges, you just need to choose what percentage do you wanna focus on apples and what percentage do you wanna focus on oranges. A lot of the time what you can do here is it doesn’t have to be too scientific even, throw out a ratio, you can be like, “Hey, what if we go 50/50 apples and oranges this time?” And people will say, “That sounds kinda good, but actually I really think it should be 80/20 apples this year,” or “No, we don’t wanna do any oranges at all.” So that kind of portfolio balance lets people share their feelings on how things should be allocated, and then within all the apples, you can pick the best apples.

Eric Boduch: That makes a lot of sense. You can see that across all their domains, thinking about marketing and demand gen, you obviously have to generate enough demand to fill the sales pipeline, but at the same time you have a brand need and a sales enablement need, and there’s a little bit of that balancing the apples and oranges.

Eric Boduch: And then within demand gen, you can optimize on your apples, the apples that are gonna work the best based upon the dollars you have there. Yeah, it makes a ton of sense, and it’s very applicable across a lot of different domain spaces.

Eric Boduch: One thing that always interests me, as a PM and as a leader, how do you tell people to strike this balance between observation and asking questions with customers?

Jackie Bavaro: Yeah, so at Asana we have a really great user research organization, and we do both kinds of research. I would say that we do pure observation a lot when we’re doing very early strategic research. So we’ll have times when we go onsite with a customer and we just watch what’s going on with them all day, and follow them around, and see the details of people who find an excuse to get up from their desk every 10 minutes. You get to observe these things that nobody would ever, ever tell you about. And that’s when we start to then fit our observations into models, and then use those models to be actionable later on.

Jackie Bavaro: But then when we get into … We actually have features and we want feedback on it, we definitely usually start people off with … A lot of times we try to make it as similar as possible as to what it’ll be when the feature’s actually launched. So if the feature’s gonna be launched with some sort of onboarding or training, we’ll try to give them that much, but then sit back and watch and see what happens. And then after you’ve observed for a while, that’s when you can really dig in with questions.

Eric Boduch: Cool. Well, thanks, we’ve covered a lot about product management today, let’s talk a little bit about the future. Do you see any particular trends in the next few years that are gonna affect the craft of product management?

Jackie Bavaro: A few surprising trends I’ve seen, one is that product management is becoming much, much more popular. Many more companies have product managers than used to in the past, many more people want to become product managers, and so it becomes a more popular field. And related to that, there are a lot more tools for product managers that have been coming out, a lot of companies that are formed around software for product managers.

Eric Boduch: Isn’t that great?

Jackie Bavaro: Yes, it’s wonderful. So some of my favorites are around making it easier to get user feedback. I love various sites where you can submit your app and then have people record a video of them using it and get that feedback that way. I think being able to get direct customer feedback earlier is a great trend that I’ve been seeing, and being able to balance it with data-driven observations.

Jackie Bavaro: I think we’re probably … I’m not totally sure about this, but we might be nearing a peak of data-driven-ness, I think that there’s a lot of data, and there will still be ways for even more companies to be getting that data in. But really, people learning how to balance and rationalize the information they’re seeing from those AB tests and real customers.

Eric Boduch: Yeah, I like that. I would say we still have a good way to go on the data, not as much of data, there’s a ton of data out there, but it’s how to use it, right? I’ve been talking a lot with customers about, “How do you model your users, your customers?” And model them in ways that make sense, what does a model of a successful trial conversion look like? What are their characteristics that are different than other unsuccessful trial conversions? And then how can you affect that, either through product, through guidance, through customer success?

Eric Boduch: So I feel like there’s a ton of data, and no product manager should be out there making decisions on gut instinct anymore, or purely on gut instinct, they should have that data. But at the same time, I feel like we could do a lot better with insights from that data, and figuring out how to get those insights. Would you agree?

Jackie Bavaro: Yeah, that makes a lot of sense, I think that there’s a lot of room for drawing insights from data.

Eric Boduch: Cool. So this has been awesome, we’ve talked a lot today. Before I talk more about you, as Jackie the person, how would you summarize your words of wisdom for today, for people listening, like three big bullets?

Jackie Bavaro: Three big bullets about roadmapping?

Eric Boduch: About everything.

Jackie Bavaro: Oh, about everything product management. So on roadmapping I would say …And strategy in general … Is I think just remembering that strategy has these three components, having a mission, having a vision, having a plan to get to your vision, which is your road map. And really thinking about being able to treat that as a balanced portfolio where you’re thinking about what goals and objectives you’re guiding towards.

Eric Boduch: Awesome, well on to Jackie. A little bit about you, favorite software product and why.

Jackie Bavaro: I love lots of software products, I’d say that one of the ones that’s my favorite now is the Trusted app, it’s an app … You might say it’s Uber for babysitters, but unlike Uber, the babysitters are employees of the company and fully vetted. And I think about … I grew up reading Baby-Sitter Club, this book about how hard it is to find a babysitter on the go. And with Trusted I can just open it up and find a babysitter three hours in advance, which I’m sure has changed my life.

Eric Boduch: I can see that being hugely useful, I know for a lot of my friends that have younger children that can be tough. And you always wanna find ones that you can trust, hence I’m sure where they came up with the name.

Eric Boduch: So, final question for you today, three words to describe yourself.

Jackie Bavaro: If I was gonna describe who I am as a PM, I would say that I’m very collaborative, I love solving tough problems, and I love thinking about strategy.

Eric Boduch: Awesome, that was great. Thanks for joining me today.

Jackie Bavaro: Yeah, thank you.

Eric Boduch: Appreciate it.

About the Author

Eric Boduch is the chief evangelist for Pendo. Previously, he served as the CEO of Brainstorm SMS Technologies LLC (dba SMaSh, Inc.) and was the co-founder and CEO of several other companies. Eric holds a Bachelor of Science from The School of Computer Engineering at Carnegie Mellon University in Electrical and Computer Engineering and is a graduate of its Executive Management Program.