Episode 236: Real Career Advice From Product Leaders

Join Melissa Perri as she dives into some of the best advice about career growth in product management from an incredible group of industry leaders. Monica Lewis from LinkedIn, Kristin Dorsett from Viator, Dheerja Kaur from Robinhood, Lucie Buisson from Contentsquare, Ben Hafele from the Lean Startup Co., Marco De Freitas and Amber Brestowski from Vanguard, Oliver Seil from Belkin International, David Myszewski from Wealthfront, and Eilon Reshef from Gong share their insights on developing strategic judgment, embracing learning, and leveraging AI for productivity.

Discover how focusing on impact over scope, obsessing over problems, and starting small can accelerate your growth in product management. Our guests also discuss the importance of market fit strategy, learning from missteps, and being open to unexpected opportunities.

Want to accelerate your product management career with practical advice from industry leaders? Tune in to this episode for actionable insights and strategies to help you grow and succeed.

You’ll hear us talk about:

  • 07:45 - Embracing Learning on the Job

Kristin Dorsett talks about not sweating the small stuff and embracing learning on the job, emphasizing that nobody has it all figured out and the value of continuous growth in product management.

  • 15:22 - Leveraging AI for Productivity

Lucie Buisson explains how using AI can enhance productivity, allowing product managers to focus on strategic thinking and customer engagement by freeing up valuable time.

  • 23:10 - Starting Small to Prove Concepts

Ben Hafele introduces the "Convinced Do Loop," highlighting the importance of starting small to prove concepts instead of trying to convince everyone at once, thereby enabling more effective product management strategies.

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Episode Transcript:

[00:00:00] Marco: I think when you're younger, prioritization sounds logical, but it's really hard to do. But I would say just be ruthless about prioritization of what you're going to build, what you're going to focus on. It's a reality unfortunately, we cannot be great at many things, at a time over time, maybe, but at a single point in time, you cannot be great at many things. And what I think you're starting. I take the bat that or I take the side of actually being good on a few things, developing fewer problems. Product features or product solutions, focus on fewer problems and say no to things.

[00:00:33] Kristin Dorsett: say what you wanna say, don't overthink it. And don't worry about being too perfect. No one's perfect. And it was definitely something I've learned as I've moved up, is that everyone's learning on the job. if you're not learning on the job, you're in something where like it's not a growth opportunity. And so if you're not learning on the job, you should find something else where you are learning. And I think having just that mindset of no, if you don't have it all figured out now, it's fine. Nobody has it all figured out.

[00:00:59] Lucie: would say ~two things. ~As a, it's not just product manager, but as a professional, if you are not changing the way you are working right now, You're gonna be disrupted. use AI to gain productivity, then you reinvest this productivity gain into thinking about what the future hold, for you, for your product, for your customer. I think you're already on a good track.

Intro

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[00:01:21] PreRoll: Creating great products isn't just about product managers and their day to day interactions with developers. It's about how an organization supports products as a whole. The systems, the processes, and cultures in place that help companies deliver value to their customers. With the help of some boundary pushing guests and inspiration from your most pressing product questions, we'll dive into this system from every angle and help you find your way.

[00:01:49] Think like a great product leader. This is the product thinking podcast. Here's your host, Melissa Perri.

[00:01:58] Melissa Perri: Hello, and welcome to another episode of the Product Thinking Podcast. Today marks the end of our special summer compilation series. Over the past few weeks, we've explored how AI is transforming product leadership and how product operations is scaling strategy across teams. Now, returning the spotlight to something that touches every one of us career growth.

[00:02:19] Whether you're just stepping into product for the first time, or navigating your path to the C-Suite, the question of what's next is always present. In this episode, we're revisiting some of the most impactful career advice shared on the show. Conversations that help define what it really means to grow as a product leader.

[00:02:34] You'll hear about the messy, non-linear paths people have taken, the inflection points that shape their thinking and the hard lessons that led to lasting impact. These are real stories about developing strategic judgment, earning trust, and stepping into leadership in ways that matter. Let's dive in.

[00:02:50] First up, Monica Lewis, VP of Product at LinkedIn. Monica reminds us that growth isn't always about climbing faster. It's about going deeper. She shares how shifting from chasing scope to making impact change her approach to leadership.

Monica Lewis: Grow where you are

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[00:03:03] Melissa Perri: Monica, ~my last question for you is~ if you had to go back and give some advice to your younger self, what would it be?

[00:03:07] Monica Lewis: My younger self was very interested in what's next? What's the next thing? Um, and I think I had a misperception that, oh wait, more things, more things on the list of stuff that I own is the way that I'm gonna grow. I remember at one point, one of my peers left LinkedIn and I, oh, who's gonna own that product area?

[00:03:29] Oh, I'm gonna make a pitch to my manager that I should own that product area. 'cause surely two things is better than one. And he just, he is very direct. He is a straight shooter. He is Monica, empire building is not your way to grow. You have a huge scope for impact, learn and grow where you are and make that impact.

[00:03:48] And I'm so glad he gave me that advice. So I think my advice in my past self is it's not to settle for the hand that you've dealt, but just like being curious, being hungry to learn and to make impact, Within what you have, is gonna be such a rich experience and set you up for future growth versus trying to play some more tactical game of like, how do I be seen as more senior?

[00:04:10] So that's what learning that sooner might have been helpful for me. So that's my advice of my past self.

[00:04:15] Melissa Perri: That is great advice for all of our listeners out there.

[00:04:17] Next Kristen Dorsett, chief Operating Officer at Viader, her advice. Don't sweat the small stuff. Learn out loud, take risks and trust that no one has it all figured out.

Kristin Dorsett: Don’t sweat the small stuff

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[00:04:28] Melissa Perri: So Kristin,~ it's been lovely talking to you. ~I got one more question for you. When you look back on your career, what do you, if you could go back and tell your younger self some piece of advice, what would you do? What would you tell 'em?

[00:04:40] Kristin Dorsett: I think it's the, so simple, but don't sweat the small stuff in that whenever some of the stuff that I used to just have a lot of anxiety about or go over and over my head of did I say the wrong thing in this meeting? Just really, it's no one's thinking about the thing you said.

[00:04:54] Everyone has moved on immediately except for you. so I think I definitely would wanna tell my younger self is just say what you wanna say, don't overthink it. And don't worry about being too perfect. No one's perfect. And it was definitely something I've learned as I've moved up, is that everyone's learning on the job. if you're not learning on the job, you're in something where like it's not a growth opportunity. And so if you're not learning on the job, you should find something else where you are learning. And I think having just that mindset of no, if you don't have it all figured out now, it's fine. Nobody has it all figured out. And that if you think they do like they're just better at masking than you are.

[00:05:28] Melissa Perri: I think that's I think that's great advice, especially for people younger in their career too, where every little problem sounds like it's gonna be the end of your career.

[00:05:36] Kristin Dorsett: No I used to, yeah, just the things I would stress over. Now that again, like it's in perspective, but it's just like it wasn't that big of a deal. like I would send it, send an email, and someone would get cranky and it's yeah, it wasn't the best thing. But they're over it. I should be over it faster too.

[00:05:52] Melissa Perri: Cool. Thank you so much for that advice.

[00:05:54] Now, Deirdre Kerr, VP of product at Robinhood. Deirdre shares a mantra that changed her mindset.

[00:06:01] Aim for a 30 to 50% chance of failure. She walks us through how that reframe helped her lean into bigger challenges and grow faster.

[00:06:09] what advice would you give to your younger self?

[00:06:11] Dheerja Kaur: Yeah. So I try to tell myself this and sometimes I listen, sometimes I don't. But it's like a way that I push myself and I definitely wish I told myself this earlier but I have this mantra that I have tried to keep telling myself, and sometimes it's still hard. And I definitely wish I had told myself that earlier on in my career, which is, everything you do, should have a 30 to 50% chance of failure. And I think the, it's super scary, right? Even just saying it makes you wanna throw up a little bit, because I'm like, wait, that's terrifying.

[00:06:37] I don't fail. I'm like the A student, who always, does well and gets good performance reviews and stuff. But I think for me especially there've been a lot of moments where, whether it's like early imposter syndrome or just like fear of failure just makes me super, super nervous to take a little bit of a leap, right?

[00:06:52] Whether that's a brand new project or challenge, like the redesign where I do nothing about design, or a new role like joining the Skim as an early stage startup from like an established company where I need something like that to really push myself to take that leap. And every time I've done it, I've been, it's been great because I've learned something's new.

[00:07:10] It's been like a huge step change for my career and my growth and my learning. But I think a lot of people who operate in this, kind of feeling of I don't wanna fail, I wanna keep being successful in my career tend to not push themselves as hard as they should.

[00:07:22] And I think having something that helps you keep challenging yourself is really important.

[00:07:26] Melissa Perri: I think that's great advice for people out there. Then we hear from Lucy Busan, CPO at Content Square. Lucy talks about using AI not just for productivity, but to reclaim time for strategy. She makes

Lucie Buisson: Use AI to reclaim time for strategy

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[00:07:36] Melissa Perri: when you're looking at bridging that gap too, and your advice for like product managers out there for thinking long term and thinking about where we're going versus balancing where they are today. What would be your advice to make sure that they're not being left behind? what should they start doing today to make sure they're set up in the future?

[00:07:52] Lucie: it's a very good question and it's a hard question. But I would say two things. As a, it's not just product manager, but as a professional, if you are not changing the way you are working right now, You're gonna be disrupted. The same way that brands are gonna be disrupted. You have a good usage of all the AI tools that are out there, you can gain up to a hundred percent productivity every day. So I would say my first advice is, think about all the repetitive task you're doing, think about the thing you don't like to do. For me, for instance, I'm not really good at writing document, it can take me like hours to write a good document. So now I'm just like, I'm thinking about my bullet point. I'm giving the bullet point to the AI and I'm iterating with the AI to create the document. And what used to take me four hours takes me now half an hour, and to think about, it's a stupid example, but I think everybody has this kind of example, of things that don't like to do or you are not really good at doing it, or you are slow at doing it. The reason why I'm talking about that is because that, for me, that's the first step because if you're able to find productivity and if you're able to save, I don't know, two for eight hours in your week. That's two for eight hours that you can spend with your customer and that you can spend thinking about, what is the future of your experience and how you can transform your experience. Because as a product manager, the issue every product manager has is time.

[00:09:22] Melissa Perri: Yep.

[00:09:23] Lucie: You are accountable for so many things when you are a product manager, that your day is already 10 full hours. So it's really, hard to not get stuck in the day-to-day and to think about your vision and your strategy and how you can disrupt yourself. So if you use AI to gain productivity, then you reinvest this productivity gain into thinking about what the future hold, for you, for your product, for your customer. I think you're already on a good track.

[00:09:53] Melissa Perri: That's great. And I like the way you phrase it too, 'cause I think there's been such a big push of AI productivity that people are backlashing against it. But that core message of if you do use AI to take away the low hanging fruit, and the work that takes you a long time but is not the most valuable.

[00:10:09] Now we free ourselves up to do the valuable work.

[00:10:12] Lucie: I used to do an hour, per week of research, now I can do the same research in 10 minutes. Let's do the opposite. let's make research now three hours, but like in three hours you're gonna do the work you, that would've required weeks of work, so again, let's, use this time we are saving to understand our market better, understand our customer better. And to your point, earlier, to talk to more human being. Also, talk to your sales team to understand how they sell. Talk to your customer success team, if you have one, to understand what are the customer pain points and et cetera. So really, like all the times that you are freeing up, use it to make sure you understand your market and your customer because that's number one job of a product manager.

[00:10:58] Melissa Perri: Focus on the human interaction part.

[00:11:00] Lucie: Yes. Yes, exactly.

[00:11:02] Melissa Perri: I love it. I think that's great advice for people out there.

[00:11:04] Next is David Zuki, VP of Product at Wealthfront. David encourages aspiring leaders to lean into what's already working.

David Myszewski: Lean into what’s working

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[00:11:12] Melissa Perri: So Dave, last question for you. What's your biggest piece of advice for aspiring leaders out there, aspiring product leaders.

[00:11:18] David Myszewski: Yeah, I think there is a handful of things. I think number one you'll. This is something that I think we learned from a previous VP of product Andy Johns, but leaning into what is working is much more likely to create outside success than fixing things, which are broken. And a lot of times some things that are working might be a surprise and that's where there's a lot of value. One of my surprises. Working on the iPhone was the day after we made the announcement we had more requests for the capability to build applications on the phone than pretty much any other request, Apple had ever gotten for anything in the entire history of the company in just a day.

[00:12:00] So that was a sign that people were really desperate to create apps. And then of course, Apple created that capability the next year and The rest is history. But I think that was an example where there is a big surprise, the amount of effort that people did to hack the phone so that they could actually build it for themselves was huge.

[00:12:17] And I think when you're looking for things like that it may not be quite crazy, maybe a little bit more subtle but as you're looking at creating those moments, I think building in some flexibility. So even if you're product is very tailored to a specific use case. A lot of times, leave the door open for people. Like you don't have to optimize it for people who might use it for something else, but leave the door open because you might be surprised at all the strange things that people do in using your product and so I think by creating those opportunities, you create some more learning opportunities that you can ultimately build off of.

[00:12:48] Melissa Perri: think that's great advice for people out there who are listening to this.

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[00:13:14] Now Amber and Marco, chief product officers for different business lines at Vanguard.

[00:13:19] Amber reminds us to obsess over the problem, not the solution. Marco follows up with powerful advice on getting close to users, being a power user of your own product and ruthlessly prioritizing.

Amber & Marco: Obsess over problems, be ruthless with priorities

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[00:13:30] Melissa Perri: amber and Marco, when you reflect back on journey in this career, starting out in this industry, what would be your advice for your younger selves?

[00:13:40] Amber: Oh, that's such a great question, very good one. I think I would tell my younger self You don't need to have all the answers Instead it's important to obsess About the problem that you're trying to solve like fall in love With the problem and then be willing to experiment fail and learn into the answers. And I think as part of that if I reflect on where we started in this conversation, my background, like you have to be really passionate about the problem to have that mindset.

[00:14:09] I'm not lying when I say I wake up every morning and think about, how do we improve retirement outcomes for investors? Because it's such a core part of my value system. So I guess, Tied to that is the age old, do something you love and you won't have to work a day in your life.

[00:14:22] Cause to me that, that obsession with problems, not solutions is really, I think the unlock to true innovation.

[00:14:30] Marco: All right. That I agree. Maybe in my case, I've, reflecting a little bit, like I would first tell my young self get to know your users, get to know your customers. I think back to the discussion we just had we maybe some, make some assumptions, and when I say understand your users is like, Go deep into the different segments of your user base and understand. And a little hint. The answer is not in PowerPoint. The answer is actually talking to them. The answer is actually listening to them directly. Really going deep and expending time with users. I think it's critical. And I think early in the record ah, no I got it. I got this. Now it's a couple of reports here and there. I read this from research, the good to go. Now go there and do yourself. I think the second one is. And then when you become a product owner, nobody should know more about your product than yourself. And I think it's go deep into the understanding of your product. You may not know all the aspects of the technology, but you need to be in a position that you're the best, the most informed person about that product. And ideally you are a heavy user of that product. I actually the big, the best product owners that I have seen are the folks that use the product. And I think those that actually. Sometimes they're not that great. It's just, you have a good understanding of it, but you never placed a trade or you never really, you never played with our portfolio construction tool.

[00:15:47] How do you know? And I think a lot of people like try to get by without it and it doesn't work. I think I tell all the time for folks in UX, go talk to your clients, but you have to use the product too, because then you understand how it works. So be a user. And then I think the last thing is. I think when you're younger, prioritization sounds logical, but it's really hard to do. But I would say just be ruthless about prioritization of what you're going to build, what you're going to focus on. It's a reality unfortunately, we cannot be great at many things, at a time over time, maybe, but at a single point in time, you cannot be great at many things. And what I think you're starting. I take the bat that or I take the side of actually being good on a few things, developing fewer problems. Product features or product solutions, focus on fewer problems and say no to things. I think when I think my younger version here was like, yeah, I can do that and I can do that too. And I can do that too. It turns out that you can't. So that would be ruthless prioritization. I think would be my advice to myself.

[00:16:46] Melissa Perri: Then we hear from Aon ef, co-founder and CPO at Gong. Aon shares lessons from early missteps and what he learned about market fit strategy and scaling the right way.

[00:16:56] Eilon. One question for you: ~before we leave. ~When you look back on your product management career and your product leadership career, what would you tell your younger self?

[00:17:05] Eilon Reshef: Oh, there's so many things like, look, my previous company was a debacle. Not debacle, but we sold it eventually, but we didn't even give the investors their money back. So I think we made every mistake in the book, all the way from not focusing on the right customers, to, really kinda not listening to the Geoffrey Moore, Crossing the Chasm, which is focused. And like I mentioned in Gong, we focused on this very small segment and went up. I think my previous company we had Estée Lauder or Cisco and American Express's first customers. It's like there's no way for you to scale that thing. so it's the strategic element of understanding how to do strategy, more than anything else.

[00:17:40] I think the other thing is, we talked about market size. I think probably thinking about what the market size is like super important because we all like ideas. Oh, I want to build something that does something, how many companies are need that or how many people need that? So more like if you kind of shoot in the right direction initially. So maybe the thing I would tell myself is, do those kind of things, listen to other people and actually follow this. And then at least if you are in a, in the right market, that's good enough, it's growing, it's then you can kinda find your spot. Even if you're not a huge success, if you go after a small market or in nonexisting market or something that isn't like a real ICP.

[00:18:20] Think there's too much likelihood to succeed. There's exceptions to everything, but we don't wanna be the 1% of this difference.

[00:18:27] Melissa Perri: I think that's great advice for people out there who are getting started or even product managers working at companies. Pay attention to your customers really really look at the market there. Great advice.

[00:18:35] Next is Oliver Seale, VP of Design at Belkin International. Oliver reflects on the power of intentional learning.

[00:18:42] He urges younger professionals to develop curiosity early, find a mentor, and take advantage of the infinite resources at their fingertips.

Oliver Seil: Learn with intention

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[00:18:50] Melissa Perri: Oliver, my last question for you is a little bit reflecting on your career. When you look back, what advice would you give your younger self?

[00:18:57] Oliver Seil: My younger self, oh, that's such a deep question. It's funny, when I was young, I just, I think it was great that I was naive about the future of my career. Like I just went for it, I don't know if I needed more advice about that. I think that was, I was very lucky that way and have been, and very thankful for that.

[00:19:21] But I probably would've paid more attention in high school. Because I love science today. I love physics and things like that, and I didn't pay attention in high school, so I didn't benefit from some of that. I think if I had been a better high school student and less of a skateboarding musician, I, maybe I would've, I, maybe I would've learned something else.

[00:19:45] But, my, I think it's just keep an open mind. Keep an open mind. And learn as much as you can consciously, and I think that's something that not everybody, I certainly didn't develop that until I was oh, an adult. So I meet people. I just say, I don't wanna go on a too far of a tangent, but one of the things we do at Belkin is we have a very close relationship with schools.

[00:20:09] So we actually have a campus, literally inside of our building, for high school students that are spending part of their week here. And just before I came to speak to you, I had a meeting with my mentee and just to see a 16-year-old who's already so much mentally advanced compared to what I was when I was 16 was super inspiring.

[00:20:31] So consciousness in learning, sounds very academic and there's probably much better ways to say it is amazing and there's just such an unbelievable wealth of insights and information to be had today. We talked about the fact that any book she wants to reach, she can just read it like two minutes from now.

[00:20:52] That's amazing and most people aren't really that conscious about it. So the sooner you develop a consciousness, find somebody who can mentor you that way, that would be amazing. Find a mentor. That's what I would tell my younger self.

[00:21:06] Melissa Perri: and finally Ben Hele, the CEO of the Lean Startup Company. Ben closes us out with a concept he calls the Convinced Do loop

[00:21:14] if you were a leader and you're saying hey, I want to invest in this. What's your biggest piece of advice?

Ben Hafele: Start small and let doing drive buy-in

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[00:21:20] Ben Hafele: My biggest piece of advice would be to prove it to yourself. Don't go all in, in the beginning. And it sounds weird, but we'll have customers, they'll come in and say, Hey, we want you to design, we from the beginning. We've never done this before. We want you to design this new framework and then we're gonna go implement it.

[00:21:38] And in a lot of cases, we'll say, no, we shouldn't do that. I know where you want to go, but let's just get, let's get some proof points because there's a key concept. It's probably the world's like most unimpressive concept. I call it the convinced do loop. And what I find is you want to do just enough convincing for this way of working to be able to do it.

[00:22:01] And then you want the doing to do most of the convincing. The approach you don't want to take is I have to convince everyone, all the stakeholders, the entire, all the VPs, the C suite, R& D, everybody that this is the best thing since sliced bread. And I have to get all the buy in. You're trying to convince the entire adoption curve in order to just get the right to do the first little thing. That just doesn't work. I'll often and sometimes people are, people will look at me and say, aren't you gonna charge of sales for the company? I'm like, yeah, I am. But I wouldn't recommend you spend that much money with us. So it's it's, we're an impact driven company and I just know that if we, if there's just, it'll implode under its own weight.

[00:22:37] If it's just so big in the beginning that we'll never actually get the right to do anything because. There's too much convincing. So balancing convinced do is probably my unimpressive framework for judging how to balance that.

[00:22:51] Melissa Perri: It's the same advice I give product managers who ask me like, Hey, I want to work this way. I want to do this stuff. and I'm like, what can you like, don't go try to convince your whole organization that you should work this way. Just take ownership of what you have convinced, like your direct people to, that you should go do it and just act right.

[00:23:08] Like act and then demonstrate, act and demonstrate. And that's how I see people make a lot of good progress.

[00:23:13] Ben Hafele: Yeah. I've never seen anything, we've all heard strategy it's culture for breakfast. And that's correct, but it's also incorrect in the way that people use it in a lot of cases, but we've never seen culture change without proof points. So it's that's the convinced do loop, right?

[00:23:26] It's I've now seen this work. I get it. I'm the next person on the little internal adoption curve. And so now I'm going to give it a shot. And it seems like it quote unquote takes longer, but it doesn't take longer because the other way just doesn't work at all. And so it's the only way we'd recommend people get into it.

[00:23:45] Melissa Perri: Thank you so much for listening to the Product Thinking Podcast. We'll be back next week ~with another amazing guest.~ And in the meantime, if you have any questions for me, go to dear melissa.com and let me know what they are, make sure you like and subscribe so that you never miss another episode of the podcast. We'll see you next time.

Melissa Perri