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49 / The Many Paths to Product Management

Hosted by Sean Flaherty & Paul Gebel



Lena Sesardic Headshot

Lena Sesardic

Consultant, Author

Lena Sesardic is originally Croatian but grew up in Asia for most of her life before moving to Vancouver, B.C. in 2009 to study Economics at the University of British Columbia.

She first started working in Product Management in early 2017 while being part of a startup-like team within a large financial technology organization. She then led an innovation team at a customer experience management company.

Presently she works as a Consultant in Product Management at the financial technology organization where she previously worked, while pursuing personal projects on the side. Her latest personal project is her newly launched book, The Making of Product Managers.

There’s no clear career path to product management. And while that sounds like just another obstacle keeping you from your dream job, it should actually come as a comfort to all you PM hopefuls. Lena Sesardic describes why through the lens of equifinality.

Equifinality simply means that the same end result can be achieved by many potential means and from many points of entry along the journey. It’s one of those grad school textbook terms you never expect to encounter again – until, perhaps, you’re talking about the path to product management.

The term resurfaced recently, thanks to Lena Sesardic, who joined Sean and Paul in this Product Momentum Podcast episode. Lena’s own journey is a story of equifinality. She is Croatian, but lived portions of her life in Europe, the Pacific Rim, and North America. Her professional life is equally diverse. Once an innovation lab product manager and entrepreneur, Lena is now a product management consultant and author. Her recent book, The Making of Product Managers, offers an up-close look at 20 real-life humans whose varied paths to product management should inspire us all.

So hang in there, you product designers and technologists. Take heed, marketers and web developers, and you mathematicians and high school educators. If product management is the field to which you aspire, it’s very likely someone has come before you to show the way.

But don’t take it from me. Tune in to hear about equifinality from Lena. Here’s a bit of what you’ll learn!

[03:24] As a product manager, I found that writing a book is a lot like building a product. Iteration was a really big part of it, and adding important features too.

[04:46] It doesn’t matter what you did before. There’s likely to be a parallel that you can draw on, and there’s no limit to who can break into product.

[06:39] PMs require such a huge, diverse skill set. Decision-making, analytical, communication skills.

[06:58] There’s also less tangible, equally important, PM skills.

[08:32] Experience isn’t just the number of years, but it’s actually what have you done. Get a taste of everything.

[10:32] Diversity of experience is key in terms of prioritization. You really need to get the full picture, to be able to look at the problem from every perspective and think about the holes in your ideas.

[12:40] PMs get to own their role because the job of a product manager is actually carving out what their job description is.

[14:22] Predict the organization’s needs. Insiders are privy to how the organization is operating, growing, and changing. As an insider, you can predict when things are going to be needed – and step in to fill that void.

[15:49] The product manager is the glue that holds the team together.

[18:09] If you can crack the code to become a product manager, you can be a good product manager – and you deserve to be one.

[20:27] Innovation through Transplanting. Taking something that’s working in one industry, spinning it a certain way, transplanting it into another industry. Just like that, you have a new service and it’s actually Innovation.

Sean [00:00:19] Hello and welcome to the Product Momentum Podcast. This is a podcast intended to entertain, educate, celebrate, and give a little back to the product leadership community.

Sean [00:00:31] Paul, I can’t believe we are at the fiftieth episode of the Product Momentum Podcast.

Paul [00:00:36] Who’d have thunk?

Sean [00:00:37] Who’d have thunk we’d ever get here? I’m so excited. Since Joe happened and I started, it was a twinkle in his eye a couple of years back, I can’t believe we’ve had the honor to interview such incredible guests and produce such incredible content for the product management space. We’ve got to celebrate. We got to do something about this.

Paul [00:00:55] We need to celebrate. Absolutely necessary. We’ve been graced with a few guests that I never would have imagined being able to pick their brains and I think it’s only fitting that we give back to our listeners in a way as meaningful as we can, sharing a couple of books that our guests have written, contributed to, recommended. So we’ve got two stacks of ten books each to give away to two folks listening right now.

Sean [00:01:22] 10 product leadership books. So go over to That’s giveaway dot ITX dot com slash five zero, the number 50. It only takes a couple of minutes to fill out the form and we’re going to choose two folks to win ten bucks each.

Paul [00:01:39] From Sean and I, thank you to everyone. We couldn’t have done this without you. We appreciate you being part of our journey. Let’s get after it.

Paul [00:01:48] Hey Sean, how’s it going today?

Sean [00:01:50] It’s going really good, Paul. That was a good conversation. I’m excited to share it with our listeners.

Paul [00:01:54] Good conversation, good book, and yeah, just a great product leader all around.

Sean [00:01:59] Yeah. She took the time to interview a bunch of leaders in our space, and it was like finding our people, right? It was like a very comfortable read and great stories.

Paul [00:02:08] Yeah. We didn’t use the word when we were talking with Lena Sesardic, but I think anthropology is sort of the word of the day. It’s a documentation of the state of the people who are doing product right now. I really enjoyed it.

Sean [00:02:21] Well, let’s share this content with our listeners.

Paul [00:02:23] Let’s get after it.

Paul [00:02:27] Well hello and welcome to the podcast. Today we are excited to be joined by Lena Sesardic. She’s originally Croatian but grew up in Asia for most of her life before moving to Vancouver, British Columbia in 2009 to study economics at the University of British Columbia. She first started working in product management in early 2017 while being part of a startup-like team within a large financial tech organization. She then led an innovation team at a customer experience management company. Presently, she works as a consultant in product management at the financial technology organization she previously worked at while pursuing personal projects on the side. Her latest personal project is her newly launched book The Making of Product Managers. Lena, welcome to the pod.

Lena [00:03:05] Thanks so much, Paul. Super excited to be here with you and Sean.

Paul [00:03:08] Absolutely. So before we get into some of the ideas that I was inspired by in your book, I want to talk about the making of the book itself. Did you find that it was interesting as an author and a product manager in your approach? Did you treat the book like a product?

Lena [00:03:24] Yeah, great question. So as a product manager, obviously I treat a lot of things as products, including this book. So iteration was really a big element of it. So the idea came from a pain that I heard from an aspiring product manager that I chat with pretty frequently. His challenge was that he has coffees with product managers to hear about how they got into product management, what they thought about the field, and he’s doing this one by one. And so what I thought maybe I could write an article based on interviews that I’ve done with multiple product managers to really showcase their stories. So it’s basically like having coffee with multiple product managers. If you read this article… so it was going to be an article. But then when I started interviewing these product managers, the stories were so diverse and just super interesting with such great insights that each product manager was providing that I decided to turn it into a book. And so the initial kind of iteration of it was really just the articles based on the interviews. It was really just a chronological story of how they broke into product management. And then slowly over time, I kind of started iterating on it and added more features, if you will, to the book.

Sean [00:04:31] So there’s clearly a theme in your book, and you just mentioned it, you know, there’s so many different paths into product management. It’s clearly not an entry-level position, but there’s so many different routes in. What was the most exciting or interesting route that you came across?

Lena [00:04:46] Great question. Yeah. So I’ll pick two that were really shocking to me. So one of them was of an individual who actually is an industrial engineer and so she worked in industrial manufacturing at a yogurt factory and then she moved into business analysis in that yogurt factory. And then she later moved into business analysis in tech, which then let her into product management. So I thought that there was a lot of parallels between the process of industrial manufacturing and software development, a lot of differences as well. But it was really cool to see her use that previous experience from such a diverse field to break into product management.

Lena [00:05:22] The other story that was also super interesting was of an individual who started in commercial banking, you know, huge industry knowledge in the loan process and commercial banking. And he actually ended up getting a product manager job without any prior experience in product management per se, but he used his industry knowledge to really break in. So those are really unique stories that I think showcase that it doesn’t matter what you did before, there’s likely going to be a parallel that you can draw on and there’s no limit to who can break into a product.

Paul [00:05:52] Yeah, I have to say, I finished reading and felt like I had just gone through therapy. It was like I had my own personal support group because the mirrors that I see in each of the stories are very similar to the journey that I’ve seen in my own career, but also in the folks who I’m leading and mentoring on teams now. And I think the way that you’ve captured those stories in a way that weaves that common thread is something special. So I want to talk about something that Sean mentioned a moment ago about this sort of invisible barrier to entry and this notion that product management is not an entry-level position. I guess I’ve always assumed that’s true, but I’ve never really heard it stated quite so bluntly. So what is that barrier? At what point does someone have enough experience or enough worldly wisdom to become a product manager?

Lena [00:06:39] I’m Eastern European, so one of my characteristics is to say things very directly, so… I really do believe that, you know, obviously a product manager, there’s such a huge, diverse skillset that you need to have. So everything from the decision-making skills to the analytical skills to the communication skills. There’s another piece to it that I think is really interesting. It’s really something that comes with maturity, I believe, maturity to make decisions. But in order to make those decisions in an organization as a product manager, you need to have that awareness of your environment and what the different functions in the company are working towards, what the motivations of the people around you are, and I think that really comes from experience, working at different companies, different industries with different people, different stakeholders in different roles as well. So really, that diverse background gives you experience to be able to judge the room and judge how people are going to react to what you’re going to decide on, right. And I think the last piece is self-awareness. So when I was coming out of university at 23, I was not very self-aware. Like my manager had to tell me to stop slouching in my chair and I didn’t really know how to write emails or how to deal with the CEO or something like that. So knowing how you deal in situations and how you deal with people I think is critical to being a product manager, because you’re going to have to be credible and you need to understand where your weaknesses, where your strengths are, and how you can best showcase your ideas.

Paul [00:08:05] Yeah. I want to ask the flip side of that question because you touched on a couple of things. Not slouching and writing emails is a little bit down the totem pole, but product management is becoming more and more popular as a chosen career path as opposed to an accidental career path. So for those listening who are aspiring to a product management career and haven’t quite broken in yet, what are some ways that you can accelerate that maturity, accelerate those decision-making skills, and get the chops that you need to kind of break in?

Lena [00:08:32] I think the biggest thing that you can do, which is echoed in a lot of the stories in my book, including my own, is starting out of university, it’s really critical to work in a company or a role where you get to do a lot of different things, a lot of different activities, working with different business functions, different stakeholders, and really having that broad range of experience is going to amplify how much experience you gain. Because experience isn’t just the number of years, but it’s actually what have you done, right. So even for myself as well, I started in kind of like a startup. So I was in customer service, but I was doing anything from marketing to operations to test security because we were doing an English language test for immigration. And so I got to get a taste of everything and that way I was able to build that kind of diverse skillset that you need for a product manager.

Lena [00:09:21] And really seeing the company grow as well, I think is important because that gives you experience. Because if you just work in one large org for a couple of years, your experience is a little bit static. But if you work at a growing company, you’re going to see multiple stages and you don’t necessarily have to now switch jobs every year. So I think that’s kind of one way to really accelerate it. And the other way is really to just kind of get involved past your job. I think a lot of people just get a job after university and they just work the 9:00 to 5:00; they go home and maybe they watch Netflix or whatever. And I really encourage people to just go beyond that. You know, read about different things, talk to different people, network, get involved with communities, and really increase that knowledge and that awareness and also that maturity and, awareness, essentially of what else is going on in the world.

Sean [00:10:08] So I’m going to pull on something you said a little earlier. You mentioned this concept of decision-making being one of the key skills of product leaders. And I have this belief that objective prioritization is virtually impossible. It’s the reason we need product leaders. And I think your book kind of shows us this, but I like to hear from you. Do you think that diversity of background helps in looking at the world in terms of how product leaders make decisions and build better products?

Lena [00:10:32] A hundred percent, yeah. So I think that diversity of experience is key in terms of prioritization because the thing with prioritization is you really need to get the full picture. If you want to get as close to objective prioritization, which we’ve agreed is impossible, you need to really be able to look at the problem from every angle and every perspective and think about the holes in your ideas, right. And I think the great thing about product management is because it’s so diverse, just like there’s no such thing as a Canadian because we’re all really immigrants at the end of the day, it’s the same as product managers. You know you didn’t necessarily, at least until recently, go to school for product management, per se. So everyone by default brings in a unique perspective. So one of the things I talk about in my book is there’s a book called The Wisdom of the Crowds by James Surowiecki. I forget how his team goes, but he’s basically an organizational theorist and what he says is that organizations actually prefer to bring individuals in from various backgrounds because they’re more likely to identify a new approach, new ways of thinking, new perspectives. And I think that’s where it’s so important for a product manager to be able to see everything from multiple sides and then use that to prioritize.

Sean [00:11:43] Yeah, you need to look at the holes in your knowledge and I think that diversity gives you the ability to do that better. Yeah, that’s great.

Paul [00:11:49] Yeah. So this kind of gets at an interesting idea that I saw throughout the vignettes that you sketched out in your stories. Product managers themselves have the common thread of diverse backgrounds. They all came from different places. But the organizations that they thrive in also have a common thread. They have this notion that Sean was just getting at of value placed on the diversity. Product managers don’t come in, sit at their desks, open up an Excel spreadsheet, and crunch numbers in a vacuum. That might be something they do as a component of the overall job, but they’re doing work by bumping into other people. They’re doing work by leading teams. They’re doing work by helping guide a vision and shape a roadmap. So I’m curious, what are your thoughts on the organization’s DNA where product managers thrive the most? What kind of activities do you see where product managers can really have that breakout opportunity?

Lena [00:12:40] Great question, yeah. So I think organizations where product managers really thrive is kind of really where the action is. So where there’s a lot of change. So let’s say, for example, it’s a high-growth startup. Maybe there’s an organizational transformation going on. And I think that’s where they really get to own their role because the big job of a product manager, on top of their existing job, is actually carving out what their job description is. I think the other thing that I want to say is there’s definitely a push towards where they can actually contribute their strategy. So in the case of Michael’s story, for example, and his story is available for free as a sample story on my website, he works in an agency as a producer, which was essentially a product manager. And he greatly prefers the types of clients that don’t have a full view of the objective of what they need the project to pursue. So he can basically provide his expertise and his team’s expertise around, you know, what problem are you actually trying to solve? Is it the right problem? How do we actually go about solving this problem? So he actually has the autonomy to use his expertise from a strategic perspective instead of just executing. So really that kind of creative nature, they can, you know satisfy their curiosity and just keep kind of pushing new ideas and formulating their position.

Paul [00:13:58] Yeah. At the end where you summarize your big takeaways, number six was that organizations promote product managers from within during these times of change, whether it’s growth or sales or agile transformations, I think the opportunities are really where that timing of talent and background meet the organization and the opportunity. And I think that is one of the common threads that I’ve seen in my experience as well.

Lena [00:14:22] I think the big thing with that, and this is an interesting point, so companies tend to promote internally. There’s multiple reasons for that and I go into that in the book. But one reason that I really, truly believe is because when you’re inside an organization, you’re privy to the information of how that organization is operating, how it’s growing, how the business functions are changing. So as an insider, you actually might be able to predict when things are going to be needed. Let’s say, for example, you’re a product marketer and you sense that there needs to be a little more help in product management, you can now jump into that and start providing that value and start transforming your role into more of a product management focus if that’s where you want to go. So it’s almost like, there are situations where an organization recognizes they need to hire a product manager, but there’s a lot of situations as well in the book where they had no idea and the person who became a product manager later, they were kind of like, “Hey, it sounds like you need product management,” and they started doing the job. So really, that insider knowledge I think is really interesting.

Sean [00:15:12] That’s interesting. So the people that have the ability to help make better decisions. Like, “Hey, you know the space, you have this knowledge, you can make great decisions, maybe you can help us guide product.” So look for that opportunity and there you go.

Lena [00:15:34] Mm-hmm.

Sean [00:15:35] Another theme that I’m picking up on is this concept of tapping into the creativity of your team, like recognizing how little we actually know and going out there and finding the holes so that we can fill the gaps and solve the problems better than any one of us could solve on our own.

Lena [00:15:49] Yeah, and I think that speaks to really what I feel very strongly about, the quality of a product manager and really kind of the short form definition in my eyes is the product manager really is the glue that holds the team together. And the pursuit should not be to be right as a product manager. You’re not the manager, per se. You’re not the person that has to make all the big decisions, like you do, but you don’t have to know all the answers. But you really have to leverage your team, your engineers, your designers, other functions, executives, all those ideas, you need to synthesize them with the pursuit of seeking the truth, right, and gathering information to support your decision.

Paul [00:16:28] Yeah. I think the moral of the story is the ability to make decisions and the background to really own the moment when it’s in front of you is really the key. Sometimes, though, the moment is not so fun. Not all the moments are mountaintop moments. The thing that I resonated with strongly is every story had a moment of challenge. Every story had a moment where there was an opportunity to learn, perhaps an unexpected twist or turn in the organizational path that they thought they were on. But there were a couple of themes that I hope to hear your perspective on just, what are the tactics that you saw most common in the product managers who thrived in the face of those challenges?

Lena [00:17:10] Absolutely. The first thing really is flexibility. So, like, not waiting for the perfect opportunity because there’s no such thing as a perfect job, and especially if you’re aiming for something in the future, you’re going to need to take little steps to get there. And those little steps are key. So in the case of Tom’s story, for example, what he did is he really utilized the tiniest of opportunities and built on top of them. So first it was he was just helping the product managers communicate with the marketing team and create marketing collateral for them. It doesn’t really seem like a big deal, but later, that allowed him to actually get on to working with the product team on a project. And then later he actually led his own project in a product manager capacity, still as a product marketing manager. So he really took like these tiny little blocks and stacked them up and with that, he finally actually became a product manager. So really utilizing every single tiny opportunity and compounding them I think is absolutely critical.

Lena [00:18:09] The other thing is kind of related to flexibility as well is really looking at your challenges as experiments. So don’t expect that everything is going to work out. So it’s funny because the journey to becoming a product manager is really similar to being a product manager, I truly believe. And there’s kind of this self-selection that happens. You know, this is going to sound a little dramatic, but I think if you can crack the code to become a product manager, you can be a good product manager and you deserve to be one. And, you know, that entails expecting failure. If things don’t go your way, you didn’t get that job, you didn’t get that project, like keep learning from your experiments and pivoting and keep moving fast. So speed and flexibility and the compounding is really huge because sometimes it can take months or even years of seemingly futile efforts for them to finally compound into everything. So seeing it as a long journey that’s going to have ups and downs I think is critical to resiliency and thriving.

Sean [00:19:06] I love that. This plays on the same theme around like, this is not an entry-level position, but the compounding is huge. Like you just have to keep at it. This is something that I’ve learned in several decades now of learning how to build products and experimenting my way into this field. You’re never done. You’re never done learning.

Lena [00:19:23] I think the key thing as well is you need to know how to compound because it’s not just… Let’s say very early in your career, I strongly encourage you to do everything that you can. Do marketing, do operations, do coding, like get involved with everything. But as you kind of go forward with your career journey, you have to start making those trade-offs. So, again, tradeoffs. That’s what a product manager does. If you want to become a product manager, you pick what building blocks you want to stack on top of each other so they amount to something, right. And that takes creativity and assessing opportunities to know what to pursue and what not for it to compound as effectively and quickly as possible.

Sean [00:19:59] Treating your career like a product.

Lena [00:20:01] Absolutely.

Sean [00:20:02] I love it.

Lena [00:20:03] Yeah, career roadmap. Yeah.

Sean [00:20:05] Well, thank you for writing the book. It’s, I think, a very cool and unique contribution to our space and for our industry. To echo Paul’s words, it was kind of like finding your people, you know.

Lena [00:20:15] I’m so glad to hear that. It’s great.

Sean [00:20:17] And really well-written. Great stories. I highly recommend it to our listeners. So I’ve got a question for you. We ask all of our listeners, how do you define innovation?

Lena [00:20:27] So there’s different ways to define innovation. The typical type of innovation that we think of is, you know, you think of something brand new that no one’s done before, you know, flying cars or something. So that’s the first level of innovation. There’s a different type of innovation. So when I used to work in the startup-like team in the financial org, my boss was a huge innovator. He invented this new web application that just completely blew up and I had a conversation with him about innovation and he was saying that it’s not always something brand new. There’s actually a lot of what he likes to call transplanting. So you see something in one industry that’s working in a certain way. And now the question is, can you take it, spin it around a little bit, and then transplant it into another industry and now you have a new service and it’s actually innovation. And it comes down to, you know, are you making things more efficient or are you making things easier? And that’s innovation in itself, right. So there’s kind of different angles of it. I think sometimes innovation isn’t as glamorous as I think we want it to be, like flying cars. And that’s OK. It’s still innovative.

Sean [00:21:31] I think micro innovations add up, right. So if you have a bunch of micro-innovations that are different and unique, even though no single one of them is going to make a big difference, you know, that accumulation of small innovations can be as powerful in building the relationship with the consumer and the users of your products as the big ones, for sure.

Lena [00:21:48] Again, compounding.

Sean [00:21:48] Yeah.

Lena [00:21:49] Couldn’t have said it better, yeah.

Paul [00:21:51] Yeah. So on that same concept, one last question. As one of the easiest ways to transplant ideas is through books, what books would you recommend every product manager have on their shelf?

Lena [00:22:02] The typical answer would be Inspired by Marty Cagan because it’s a Bible, but I’m going to spin it up a little bit. I’m actually going to say it’s The Mom Test by Rob Fitzpatrick. So it’s actually my Bible for talking to customers. He has an excellent framework where the idea is, you know, the mom test. Because if you ask your mom whether something is a good idea, she’s going to tell you it’s great because she loves you. So you have to really, you know, talk to customers in a way that’s not going to make them tell you what you want to hear and that’s where you got the real sources for product ideas.

Paul [00:22:33] Great answer. Well Lena, thank you so much for spending your time with us today. Like I said, it felt a bit like therapy. It’s been a great collection of stories that mirror my own journey, and it’s been really helpful to hear your perspective on them firsthand. So thanks again.

Lena [00:22:47] Thank you so much. It’s been a pleasure.

Paul [00:22:52] That’s it for today. In line with our goals of transparency in listening, we really want to hear from you. Sean and I are committed to reading every piece of feedback that we get, so please leave a comment or a rating wherever you’re listening to this podcast. Not only does it help us continue to improve, but it also helps the show climb up the rankings so that we can help other listeners move, touch, and inspire the world, just like you’re doing. Thanks, everyone. We’ll see you next episode.

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