Practical Product Management · 2025-10-08 · 53 min
Key moments - from our scoring
Substance score
39 / 100
Five dimensions, 20 points each
Steve, a product leader at Expedia Group for 8.5 years, joins Leah and Marilyn to discuss the fundamentals that separate good product managers from great ones - focusing on language precision, data-backed conviction, and the courage to have a point of view. The conversation explores how writing excellent problem statements with carefully chosen language sets teams on the right trajectory, why selecting the correct success metrics matters, and how pattern recognition built through repetition allows experienced PMs to trust their instincts while remaining intellectually honest about bias. The hosts dig into how these fundamentals transfer across industries (payments, fintech, e-commerce, travel), how to convince skeptics when you don't have time to gather data, and why younger product managers must learn to show up with recommendations rather than options. Steve emphasizes that the devil is in the details - word choice in problem statements can completely change solution direction - while Marilyn critiques surface-level thinking enabled by tools like ChatGPT that lack substantive backing. For product leaders building teams and junior PMs navigating their first leadership moments, this episode clarifies how conviction, storytelling, and intellectual honesty compound over a career.
Writing an excellent problem statement with precise language is the most critical fundamental; if the language is off by even one word, it can lead to a completely different solution set and poor problem-solution fit. Getting the language right and understanding the problem deeply sets teams on a strong trajectory.
Product managers should state their assumptions explicitly - distinguishing between objective facts and subjective judgments - and be intellectually honest about when they're not being objective. When challenged, they should gather supporting data and narrative, but it's acceptable to say 'I've got pattern recognition from past experience' as long as they're transparent about potential bias.
Senior PMs combine three things: confidence and conviction backed by data, a blend of both quantitative and qualitative evidence, and strong storytelling that gets people on board. Junior PMs often present problems that feel 'squishy' without breadcrumbs of data or the ability to articulate the problem clearly with supporting narrative.
Word choice in problem statements has material consequences; selecting the wrong word changes the meaning entirely and can send a team in the wrong direction. Precision in language is a detail that directly impacts whether a team solves the right problem.
Frameworks for writing problem statements, focusing on details, and establishing success metrics are fungible across industries - they work the same whether you're in fintech, travel, e-commerce, or payments. What changes is the context and domain knowledge, but the scaffolding of product management discipline carries forward regardless of industry.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode circles a few reasonable ideas (problem statements, pattern recognition, bravery, time-boxing debate) but delivers them mostly as familiar platitudes with heavy padding, tangents, and repetition rather than dense, non-obvious claims.
Nailing the basics leads to good results
Most decisions aren't as big a deal as they seem in your head as well
Almost entirely recycled product-leadership tropes - 'words matter,' 'disagree with me,' Brene Brown's firm spine/soft front, and the power of the pause - with little contrarian or first-principles thinking.
So Brene Brown talks about, um, um, firm spine, soft front
all sizzle, no steak a lot of times
The guest is a genuine practitioner - a product leader at Expedia Group for 8.5 years with prior fintech experience - but is a mid-level PM rather than a senior executive who has operated at true scale, and the transcript stays generic.
I've been with Expedia Group for eight and a half years, coaching, leading, mentoring, managing a variety of different spaces
I worked at Discover Card for about three years at the start of M my career
Companies are named (Expedia, Discover, Hallmark) but virtually no metrics, dollar figures, timelines, or concrete case detail; the pandemic and 'culture change' examples remain abstract and hand-wavy.
0 people are buying anything
that has, that has gone a long way for me
Hosts ask a few decent open questions and one guest even flips a question back, but the conversation is mostly mutual agreement with long personal tangents (poker, road trips) and no real pushback on claims.
how have you convinced people, like, I have the reps
How do you balance that with sometimes expediency of getting stuff done
Computed from the transcript - who did the talking, and the words that came up most.
In this episode of Practical Product Management, hosts Leah Farmer and Marilyn McDonald are joined by Steve Brieloff, a seasoned product leader from Expedia Group, for a conversation about what truly defines great product management. Steve shares insights from his years leading teams across Expedia’s product suite, highlighting how getting the fundamentals right - from crafting precise problem statements to choosing meaningful success metrics - sets the foundation for success. The trio dives deep into the importance of language, the evolution of confidence and conviction in product decisions, and how bravery shows up at every level of a PM’s career. From building trust through vulnerability to balancing open debate with decisive action, this episode explores how mastering the basics and leading with courage can transform teams, culture, and products alike. Key Takeaways 1. Master the Fundamentals - and the Words You Choose Matter. Great product work starts with writing a precise problem statement and choosing the right success metrics. One misplaced word can send a team in the wrong direction. 2. Bravery is a Core Product Skill.
Transcribed and scored by The B2B Podcast Index.
Speaker A: M welcome back to Practical Product Management. This is a podcast where we focus on doing product management in context. So there's lots of great books, lots of great theory out there. You should read about that and study that for sure. But good product management happens where you are in the season you're at, with the team you've got in the company you have with the leadership team, you have all of those things. Um, so today we're super excited. Steve is joining us as a guest and we're going to talk for the next bit about what he's passionate about in product management. So, Steve, why don't you introduce yourself and then we'll dive in.
Speaker B: Sounds great. Thank you, Leah. And thank you, Marilyn. Excited to be here on the podcast, Excited to talk product. Um, I have been a product leader for, um, a while now. I've been with Expedia Group for eight and a half years, coaching, leading, mentoring, managing a variety of different spaces within the product suite. Anytime you're going onto Expedia Hotels.com or VRBO searching for a place to stay, I'm one of a series of product managers that touches that experience. So if you have feedback, I'm more than open to that. Um, two things that have really been foundational in shaping my own career journey and my path into product management. One is I have a history of educators in my family that have really instilled this learning mentality and mindset. Obviously from a traditional educational background, I've seen that really carry through into my time as a product leader, both as someone who wants to grow and continue to progress their career, learning new and different things, but also teaching other people around areas that I'm passionate about, those specifically being product. The other area that has been, um, fundamental in shaping how I've arrived at the place that I'm at is a focus on getting the fundamentals right. And for, for me, that has come from a background playing sports growing up, where you just gotta practice these little movements over and over and over again, get those right, and then the results start to take care of themselves. I've seen that to be true in my time as a product leader as well. Nailing the basics leads to good results. So I'm excited to be here, excited to dig in a little bit further.
Speaker A: Awesome.
Speaker C: I like it. Welcome to our chaos.
Speaker B: Steve, that sounds like product management. It is chaos.
Speaker C: It does too. I mean, that's why we're all here. Um, I think, you know, you said two things that probably resonate with both Lee and I and everybody on the call Is, is one, um, you know, part of our jam is all about bringing teams together and building teams and, you know, whether that's people that report to you in the same job family or whether that's a team that's going to deliver a thing. And then two, the focus on the fundamentals. Um, so I love the sports analogy, even though I'm not a sports guy. Uh, but what do you believe the fundamentals are? Tell us more.
Speaker B: Yeah, there, there's a number of interpretations out there. The way that I think about the, the fundamentals of product are what are those critical inputs that go into making some of those key product decisions? The most basic of those fundamentals, in my view, is writing an excellent pro problem statement and understanding that problem so deeply and so thoroughly that you just know you've got the right thing. And I spend a lot of time with my product team focusing on the language that gets selected for that problem statement. If the language is off by one word, it might mean a completely different thing. Therefore, the solution set that you select might be in the wrong direction and you might not end up having that problem solution fit that you really want. Whereas if you, if you go really deep into the data, you spend a lot of time thinking about the language of the specific, the specifics of that problem. If you get that right, you're setting yourself up on a really strong trajectory. So that to me is, is the most essential, basic element of a, of fundamentals. Say one other key one that comes to mind is choosing the right success metrics. So this is obviously a, uh, big thing as a product leader and a product manager is how do you measure what, what I've done and how does it matter and a lot of ways to interpret this, but it's essential to have a point of view. I think you're, you're, you can be right or wrong, but as long as you have a point of view, you're, you're pointing the team in, in, in a direction and that is more important than just fumbling around. But as it, as the team matures and the products mature, having focus on the right success metric, which will vary based on the product you're working towards and understanding that deeply what the levers are that's going to help set the team up for success.
Speaker C: Uh, yes, yes, yes, yes. I'm just actually thinking about so many scenarios in my life and Lee, I know you've come across this too, or that, that have an opinion thing. So when you're younger and when you're newer in product management, it can be really hard to have an opinion because you don't want to be wrong or you don't want to be argued with. And if you tell the team to build the wrong thing, like, you're going to be wrong. And I think that's the first big, brave step into, like, becoming a product manager is to actually know enough where you can have an informed opinion and you can set the trajectory for the team.
Speaker A: Yeah, yeah.
Speaker B: And being willing to be wrong is the other thing, too. When you're more junior, you're fearful that if you're wrong, it's going to be looked down upon, that you don't know anything and you won't get any opportunities. But in reality, I love to raise my hand and say, um, I might be wrong here, but so somebody can check me on that one. That's a superpower in and of itself.
Speaker A: Yeah, well. And I think, like, I really like what both of you said. I think that one of the things that I think is a cornerstone, this is not about product people, but about leadership, is when you. The way that you start to inch towards leadership, in my opinion, when you're a young pm, when you're young in your career, is when you learn to show up with a recommendation. The people who show up to me and are like, these are the five options. I'm like, I could have done that. I could think of 10 more. But bringing me five options and then saying, but these four are nonsense, this is the one I would go for. Well, now we're talking. Right. Uh, so I'm curious what you think. Like, how do you think people, you know, when you talk about problem statements and defining that problem statement, what do you think starts to separate sort of the newbies from the people who become professional at what we do? Uh, when it comes to making problem statements.
Speaker B: Yeah. I think it a key aspect of the difference between a more junior and a more senior product manager in that sense, someone who has confidence and conviction in the choice that they've made and has the data and the narrative to back it up. I think a lot of times you could put forth a perspective on here's the problem that we're facing, but it just feels a little bit squishy. And I think for outsiders that are more seasoned, you can see through these things. You can, can see when, you know, I don't think there's really a problem here. Um, and that might be based on tenure and experience and your ability to project confidence, but I think as people mature, they're able to not only Articulate a problem in a way that is clear and you can just get it right away. But also there's breadcrumbs, uh, of data that point to this specific problem, and both a blend of quantitative and qualitative data.
Speaker A: And.
Speaker B: And then I think that third part is a storytelling element that the product manager, product leader is able to bring to the table and get people on board with and convince them that this is the problem that they need to solve for. And then here are the series of solutions we need to go forth and address in order to. To build towards solving for this problem. So I think it's that. That package having that confidence, conviction, the storytelling, the data element, and that strong point of view.
Speaker A: Yeah, I love that. Just remember, uh, since we started talking in my head, I can remember a version of Marilyn who has said words matter so many times in. In meetings that I've been in that I'm like, Marilyn's. This is when Marilyn's going to say words matter.
Speaker C: Words matter. It is too. Um, I like. Yeah, sorry, you had. There's a lot of things that spun my head in a couple of different directions. The first one was the words matter. Like, it is. It's important to be really precise.
Speaker A: Yes.
Speaker C: Um, and they have meaning. Right. So you can't just, like, whip another word in there because it completely changes the meaning of what you're doing. Right. Um, yeah. I also think that. That, like, you know, the conviction on the. On the problem, um, and the data and instinct to back it up. I don't actually think it's always instinct. I think instinct is like, um, maybe it's sort of like the subconscious digestion of all the data and information you have. Um, but I do think it just starts with knowing your stuff. Right. Like, go deep. And as someone who's starting into a new area right now, um, I mean, it's. It's scary to kind of be like, well, I don't know what that is, but I'll figure it out. Um, and then do the work to figure it out. Because I think the people that stay at the surface level. And now I'm going to complain a little bit, which I tend to do in every podcast. Steve. So, sorry. Um, that I've seen this propensity of people to turn to tools like ChatGPT and Just Sor. Of, like, whip out an answer that at the surface level sounds intelligent or plausible, but there's nothing behind it. Like, there's no way to inspect it or ask questions. And then, like, it's just this really Sort of surface level, gloss. Um, I think that depth of knowledge is really super important.
Speaker B: Yeah, it's all, all sizzle, no steak a lot of times.
Speaker C: Right.
Speaker B: So I, and I think that the, like, the instinct piece that you can use to complement a chat GPT output is pattern recognition. And so that comes with time, doing the repetitions and learning over time. So, Marilyn, I know you're in a new, in a new role here, but you've also, you've seen a lot of the patterns before, so a lot of the learning that you're likely going through is context specific. But you can then marry that, ah, new context up with the patterns that you have from your past history and have confidence and conviction in the path forward. So I think for newer product managers who don't have that level of pattern recognition, it's. How can I, uh, acquire a stronger and higher level of pattern recognition that comes from doing the work? And the work obviously looks different in an AI world than it did 10, 15 years ago, but you can still need to take these steps. And the fundamentals that I preach to my team, they still exist, even in an AI world. And you still have to pull together data. You might be asking ChatGPT to find some data for you, but you still need to weave that together into a narrative that makes sense, gets people compelled to stand behind you and say, yes, Steve knows what he's talking about. That's key.
Speaker A: Yeah. Marilyn and I have the exact same pattern of. So this, this assessment, the six types of working genius, and our top one is discernment. And discernment sounds like intuition and instinct, but what it actually is is pattern recognition and the ability to look at a puzzle and go, that's not right. I'm not sure why, but that's not right. You know, just because. And it's quick. And Marilyn and I are both very quick to make decisions, but a lot of it is because if you put something in front of me, I'm like, yeah, I know what we should do. And everybody's like, how. How could you possibly know? And I'm like, I just do. I don't know how to. I mean, I can go get you the data, but a lot of the data isn't right here. Because I've been around this corner a number of times, and I know what's coming. And I think that's. That's one thing, but I think that, for me, is why we do this podcast. Because the amount of young product managers who have said, well, that's not what Marty Kagan Says. And I'm like,
Speaker B: God bless Marty Kagan. No, no. This specific that I'm working on, probably not.
Speaker A: I love you, Marty, but no, he does. He's not worked here. Right. And so I know you read a book and it told you how to do it, and I'm telling you to do it differently.
Speaker B: So I'm curious, Leah, for you, though, how have you convinced people, like, I have the reps. I've. I've got the experience. Just trust me. That can come across in a way that you don't want it to.
Speaker A: Yeah, no, totally.
Speaker B: So then how do you. How do you get people on board?
Speaker A: And that's. So that's the thing about that particular, um, that particular style of. In the working genius that I tell people who have that as a genius, like, you will be absolutely crushed by how often you're asked. Somebody says, prove it, and you are like, okay, let me go back in and explain what I see. And so it. So what I have learned to do is when someone says, yeah, okay, but how? Then I do have to go back in and break it all back down and try to then build the narrative so that they understand. I quickly got to information, but now I need to go unpack the information so that they can come on the journey with me. Because Marilyn and I are favorite. The favorite phrase we've both heard over and over in our careers. Um, so I will have to go back in and break it down. Sometimes I will have to go get some data, right? Because it's not like I do things in an absence, in a vortex of no data. Right? But I sometimes don't need us to go gather a bunch of data, because I can look at it and go, there we go. If I'm then asked to prove it, I need to go get some information. Right? I need to go. Go get that data to prove it. What I think. So I've done that. I will go get data. I'll talk to customers, I'll go talk to stakeholders. I'll gather the information. I'll build the narrative and say, this is my hypothesis. This is all the information that now backs up that hypothesis. Yep, it is. I did go get information that backs that up, but I also looked for other things that could disprove what I think. Right. Um, because I'm. I am intellectually honest, so I do know that I will try to tune things in the direction of what I want. And if I'm gonna do that, I say that, listen, I gathered this information. It backs up what I said. I actually Don't. I don't think I'm objective. I think it's okay to say I'm not objective here.
Speaker C: Yeah.
Speaker A: Because sometimes I'm not. Sometimes I squarely am not objective. And I will not go get data that backs up someone else's idea. Right. Um, yeah, But I'm dishonest about that. I'm just willing to say, like, this is not objective. This. But this is the information I have that makes me think this is how we should go. I do think that if you're someone who has strong pattern recognition and you have a history behind you across time, the more right you are, which is why that's a leadership principle at Amazon. M. Right. When I first joined Amazon, I found that is right a lot leadership principle, really confusing until I realized that when you have good pattern recognition, you're just right a lot. Your gut is good because you go, yeah, I've been here. And the more you do that, the more people will just go, I don't know. I don't know why Leah thinks we should do that, but go ahead. You know, and I certainly have been in rooms with Marilyn where I'm like, I don't know why she wants to do it that way, but let's do it that way.
Speaker C: Right.
Speaker A: Whatever. I trust her, you know, and if we get it wrong, we'll. We'll come back to this point and figure out how to take another step. So I think there are usually, uh. The answer is, as usual, it depends. It depends on what I'm being asked to back up.
Speaker B: Yeah. So one interesting thing you mentioned in there is you. You called out when you are, um, when you're not objective and you feel like you've got a lot of confidence and conviction in something, maybe you are ignoring the data, but at a minimum, you're stating an assumption that you are not being objective. So that is also a critical fundamental of product management is stating those assumptions. And some of those assumptions might be very objective, like, sure, I don't know, we have to drive X metric or what have you. But some of them might be very subjective, like what you had called out. Like, maybe you have some past history or a family relationship to something. I don't know that working on the product at Amazon that you can bring forth. But you're like, I know that this is the right way to go, and I'm ignoring everything else. And that's fine, because part of the product role is to make judgment calls. So you're trying to, trying to lower the risk on judgment calls. That's really what we're doing 100%.
Speaker C: I think one of the really interesting things about all three of our careers is that we have switched, uh, industries. Um, so we've applied the same skill to different spaces. Um, and we sort of started here. Yeah. Like, I'm entering a new space and, uh, you know, the patterns apply. Even though the thing I'm building is different. The problem I'm solving for the customer is very different.
Speaker A: Yeah.
Speaker C: Um, and I don't. It's not like I have the, like, deep knowledge of the user yet, but, you know, I'll get there. But the patterns apply. Right. So I can already start to see some of the early patterns coming through. How has that helped you, Steve, in your career? And then I'll ask the story, same thing to Leah. Like, actually, actually think it's super critical
Speaker B: to, to navigate, to retain those patterns and pull them to other contexts. Yeah. So I think this is why I've got such a focus on the fundamentals. Because, like, this is a skill set that carries with you no matter what.
Speaker C: Yeah.
Speaker B: I. Some of the frameworks that I've used to write problem statements, you can extrapolate and drop into any context, whether it's payments, whether it's E commerce, whether it's, I don't know, sports, esports, what have you, like, it should make sense no matter what. And so that's why I've got such a focus on kind of the scaffolding of product management, because that builds up my own skill set. Now in terms of my own experience, I worked at Discover Card for about three years at the start of M my career. I've been at Expedia for eight and a half since. And I really started to focus in on getting these little details right when I was at Discovery. Now my role is vastly different at that point in my career. And I remember a product leader was saying, uh, the devil's in the details. And at the time that just felt like kind of fluff, like, what does that really mean and does it really matter? Can't we just ship the thing and move on and be done? And what I found as I've matured as a, as a leader and product manager is that it's very true. The devil is in the details. And that's why I spend so much time harping my team on my team around, pick the right words. So I love your framework of, like, the words matter. If we pick the wrong words, that is a detail that we are ignoring. And if we really key in on that, the language around a problem statement that's going to set us on the right trajectory. So I think I've seen that detail oriented mindset as a product manager has really transferred effectively. Has nothing to do with the fintech space at uh, Discovery Card, has nothing to do with the travel space at Expedia. Is something that should be pretty consistent no matter what the next jump or jumps look like. For me. I'm sure the same is for both of you as well.
Speaker C: Yeah, I'm a little to. Yes. And because I'm a very different personality type, I will tell you that. Um, and, and I like, I'm a huge fan of all of like line them up. I'll do the disc, I'll do the insides. I've done that. Like the Hogan, like stack them all up. They kind of, kind of say the same thing about me. Um, I freaking hate details. Like I have a big picture, I'm high energy, I like to rally a team. But like you can grind my soul to shreds on the details. Having said that, details matter in product management and if I approach it from a user perspective backwards, um, I can get really sort of like wound around the axle about very precise and detailed things. Um, so I think there's like this, you know, how, how you approach the problem and how you, how you help it fit your personality. Uh, but okay, so I promise you, Leah, I was going to ask you the question about um, the same one I asked you, but I'm going to flip it, um, because I think it goes back to. The purpose of the podcast is that we have these frameworks, right? We have these mental models, we have these things that are pretty fungible. You can pick them up and you can move them from one industry or one group to another, but the context always matters. Um, so like maybe you talk about how something you've brought to Team A needed to be tweaked to take to a different team. I'm not like, I didn't sign up to interview both of you for this podcast playing along with me.
Speaker A: Yeah, I'm trying to think of an example. I think, you know, I, I will. So I, the first thing that come to my mind is, you know, in, in the leadership journey I've been on over the last, whatever, whatever now five years, I had really overhauled and built some teams in uh, in one space and my background is very heavily in payments and, and E commerce and fintech and came out of that space and was going to go into this travel environment and then the pandemic hit and all bets were off. I had to rethink how I approached so many things. I could use my connection skills, I could use the frameworks that I know how in order to, like, look at the problem. But the context was totally different because we. I couldn't make business happen. I couldn't make anybody go anywhere because we couldn't go anywhere. And so it was. It was a moment in time where I had to really rethink how to approach my team, but also how to approach the customer problem and how to use the data we already had in order to make decisions about what we were going to do while it was quiet. And that was a really interesting journey because it was, you know, I had been at Expedia, but it was new industry for me because it was very different, um, part of the travel industry. I was the CTO and the cpo, which was new for me. And we were in the middle of a global pandemic that had shut the business down. And yet I needed to. The company was relying on me and my team to build walls quiet so that we could run on the other side. And that required me to bring some sort of fresh eyes while still leaning heavily on what I know how to do. Well, and. And I think I would just tell everyone out there, there will be moments in your career when you either switch industries, switch companies, switch leaders, switch whatever, and go, oh, shit, what have I gotten myself into? Can I do this? You can, you can. It will just require you to use some of your old skills and to build some new ones.
Speaker B: So I think there's a. There's a piece of this too, where it's certainly applicable for product, but likely across all, just putting your foot out there, going into uncharted territory. Obviously a pandemic is a great example where nobody knew anything. Very uncharted. I remember that time at Expedia too, where it was like, what are we supposed to do here? 0 people are buying anything. It's very strange. And so it was just, how can I. Some. At some point it was, I need to step away from all of this history that I've learned and relearn a new way of doing and thinking and get rid of some of the process, make decisions really quickly, ensure that you were grounded in what the needs of the traveler was at that point in time, and then make decisions that you think are going to be the right thing, um, for this period. So there's that broader context of who knows when things are going to end, but ultimately there we all have to be brave I think as product managers, you got to be willing to stand up for what you believe in. You got to be willing to take some risks. You got to be willing to make some people mad, and that's really hard. I do not like doing that, but it is a reality of. Feels really uncomfortable for me when other people are mad, and it's my doing. That's something that I'm working on. But I think that's a. That's a key part, and it's an interesting contrast for me as I talk about the fundamentals and stepping out and being brave. You may need to step out from those fundamentals at some point in time in order to push in a certain direction or make a specific point. Knowing when to do that is a skill that will get. That you can gain over time just from, I think, again, recognizing those patterns and knowing, is this the moment, or is there a different point in time that I need to step out?
Speaker C: I love this notion of bravery as a key skill. And, um, I'm going to be honest with you. Like, I never really thought of it as. As a key skill. Like, um, but it kind of is. Like, you. You have to make a call. You have to make a decision. Like, you have to set the charter for the team to be the. The advocate for the customer in the room. You have to use your voice, and that's pretty brave. Um, and I think more you do it like the. The bossier I get. I'm not gonna say you guys get bossy, but I certainly get bossy. The more you do it, the easier it gets.
Speaker A: Yeah.
Speaker C: Um, but bravery is kind of a cool key skill. I'm. I'm stealing that one. Um, absolutely.
Speaker A: Um, I mean, it's one of. So it's one of my four core values is. It's courage. Right. And I mean, with. I bucket into courage, bravery and risk taking and saying yes, faster learning on the run, like, all of those things sit in courage for me, um, because I do think it's required. And so Marilyn has got her frowny face on, and that's why I'm going to ask her to tell us about when she feels like she's been the most courageous.
Speaker C: Oh, my gosh. I mean, it's just that my frowny face is my thinking face. I, like, I need more Botox or something because you can. Like, I'm pretty easy to read from a poker player perspective. Um, bring your.
Speaker A: Bring your paycheck and come over John Scott camp me. I want Leah to bring her paycheck and come over to the poker game. I'm like, shut up, Steve.
Speaker C: Like, like I'm gonna sidetrack just for a minute. But like, I do like a good game of Texas hold'. Em. I think it's fun. And we usually have like, I don't right now, but we usually have friends where we can play like poker nights.
Speaker A: Super fun.
Speaker C: And you know how like poker players have cool names like Snake Eyes or like whatever. My poker name has always been the donor.
Speaker A: Okay.
Speaker B: Because you're, you're losing your money a lot.
Speaker C: The funniest thing is, is I'm pretty erratic. Um, and so I do pretty well. Like, I make it to really late in the tournament and it just pisses people off.
Speaker B: Um, but it's because unpredictable.
Speaker C: It's exactly right. I'm always like, like,
Speaker B: yeah, bucking the trends. Right. There's a right and a wrong way to play every hand. But you're saying there' more than one way.
Speaker C: I'm just having fun, man. Like the $40 or whatever the entry is for me is the price of entertainment. I have no intention of winning the whole thing. I'm just having fun. Um, yes. So basically I just got myself uninvited from every poker tournament that anybody's ever heard of.
Speaker A: No, they'll take your money.
Speaker C: They will take my money. But they'll just be mad about how many of them got knocked out by me when I was doing stupid stuff.
Speaker A: Yeah.
Speaker C: Um, yeah, sorry. To go, to go back to like, uh, to go back to bravery, um, I think you guys just sort of gave me a new paradigm, which is what the look of my face was. Um, and I think that there's a, like a couple things. I'm actually sort of like running this up and down the whole chain of my career as I'm thinking about it. Because you, you know, as an ic, like that's the first thing you learn. So a junior product manager, like probably one of the key skills is to be brave, to say I don't have the skill or I don't know that, or like I don't understand the problem and sort of like just go figure it out. There's a whole bunch of bravery in there as a first time manager. Like, uh, you're. There's a bunch of bravery around letting someone do the job differently than you do it. Because that's a, that's a key skill of that job. Right. And most first time managers are like, you have to do this thing exactly like I say, or it's a baby reindeers are going to die. Or whatever. And that's why first time managers are all horrible. Um, and then as a leader, like the bravery to say here are the metrics that we're going to use to measure and run the business and we're not going to falter even when things are looking a little bit shaky. But these okrs are what we're going after. Um, or then determining when it's time to pivot because you don't have enough information. All of those things are bravery. So yeah, that, that was what was going on in my, in my face when my brain was ticking. Leah. Um, totally. Uh, it sort of like holds at every level and I think that you just, you know, you change my paradigm a little bit. Thank you very much.
Speaker B: I one, one thing I'll hit on for, for bravery. I, I think there are, there's a lot of cultural baggage that every organization has that makes it really hard to be brave because you've got all this inertia going behind. This is how we do things here.
Speaker C: Yes.
Speaker B: And when you are one person or two people that step out and say, you know, that doesn't make that much sense anymore. That's really hard. It's really difficult to do. And you need to find one, two or three people that are in that camp of like, maybe I can switch over and maybe they can then help be catalyst to get the rest of the organization to switch their ways of doing things. And the way that that culture is operated, that part's really hard. But I know from my own experience, I've fortunately been able like see some of that change through in a couple different ways. One of them is how the team talks about learnings at the organ. Yeah, um, we didn't really have a good mechanism of it and it was very surface level and I was like that it does. It's not good enough. Like we need to go a little bit deeper and was able to convince a uh, handful of the right people to shift and say, you're right, we do need to go a little bit deeper and here's how we can go ahead and do it. But that's it. It's really hard to do some of that level of cultural change. So as you are thinking about what are some of those areas that I can be brave in and what are some of the big swings I might want to take to shift a culture or switch, shift a product. Know that there are some potentially like outside forces that you're going to need to fight against and, or figure out how you can channel those in a way that are going to help become sail, wind at wind at your back as opposed to headwinds.
Speaker C: Yeah. Culture change is like this whole basket of cats. Um, and uh, I, I, I think it's um, incredibly rewarding. Um, and it is also some of the hardest stuff I've ever done. And um, so when you like, even with like, let's talk about a big company, I don't have either of you guys read this book called, um, unraveling the Giant Hairball or Unwinding the Giant Hairball.
Speaker B: I read it a long time ago.
Speaker C: It's like this really old book, um, about Hallmark back in the day. And it's like tiny. Um, and we'll put a link on this podcast. Um, it has to do with how you build culture in a smaller group. And when you're part of a large company, obviously expedus, hugely, you've been part of massive corporations. When you're part of a large company, it's really hard to change culture because, and it's really hard to change culture in any company because you have a set of humans that have career success, doing a thing, sitting at that desk, acting a certain way up until the point you walk in the door and then you're like, you know, an event happens or it's, you're the event and you're like, we need to pick, we need to change. Um, humans are like, we're pattern people, right? And we want to push that little lever and get our little dopamine hit and be successful. And it's really hard to let, to let a group put down all of those preconceived notions and change themselves. Um, so anyways, that book has always been like one of my favorites. I think, um, systemic change across an organization needs a lot of support. Like I've seen it done well, I've seen it done really terribly. Um, so I think you either need to like have a structure, um, and a change process and all of this sounds really heavy and governance y and it's not really. You just need to have thought right, um, and metrics and understand your user and your problem and all sorts of product managing things, um, or the other way I've seen this be successful is to carve off the Skunk Works group like they explained explain in the Orbiting the giant. Orbiting the Giant Hairball. That's the name of the book, um, carving off the Skunk Works group that's allowed to operate different. They stay close enough to the mothership that they get the benefit of being part of the mothership. But they're, they're individual enough that it's okay for that group to act and operate a little bit differently. Um, so I, I, you know, and, and sometimes the best results are a combination of the two because there's pros and cons of doing any of that. But. Yeah. Ah, culture change. Sorry, another, another soapbox. I just hopped back up on this.
Speaker A: Okay, I was just going to mention I do actually have a basket of cat.
Speaker C: Oh, you do. Awesome. Let's unwind that basket of cat.
Speaker A: So it's interesting because both of you have sort of touched on something that is really fascinating to me. So Brene Brown talks about, um, um, firm spine, soft front. Right. Firm back, soft front. And the idea is that we are, we have a, you can have a spine of steel and have an opinion and make decisions and be absolutely strongly convicted about something, but you need a soft front in order to connect. And so I, as we talk about sort of courage and bravery, I wonder, Steve, how that shows up and how you lead and how you lead teams and how that, how, you know, how do you bring those things together?
Speaker B: Yes, I think that there's a, there's a number of elements. One of those, one of those being you just gotta be able to connect with people and build relationships. And so I think when you have the need to do some of that level of culture change, you need to have done a lot of work ahead of that point in time to create the right stepping stones and build those relationships so people trust you. And that could look like when you're a new product leader, product manager, an organization, just talking to some of those key stakeholders, asking what their biggest problems are and just go fix those things right away, like whether they're the most important thing or not. You're going to be building a level of internal empathy that you can then leverage down the line and have these stronger relationships starting on the right foot. Because if you have one of those relationships that's with a key stakeholder that starts off on the wrong foot, you're done. You're not going to get any help in the long run, and you're really putting yourself back a lot of ways. So that is really step one for me. How can I listen to people? How can I ask what their needs are? How can I demonstrate that I'm willing to help them and then follow through on it? That is a key piece of it. Um, I think the other, the other thing that I think about when I'm trying to build and lead strong product teams to be brave is to Encourage them to disagree with each other. So I, uh. I love giving my team permission to tell me when I'm wrong. And that can be really hard and really scary for especially more junior employees to tell their manager. I don't know about that one. That doesn't make sense to me. But it's. It is my job to create a culture and an environment where they can disagree with me.
Speaker C: Right.
Speaker B: Because that then gives them permission to have these strong ideas. It gives them autonomy to carve their own path, and it creates a further level of trust between the two of us. It also democratizes the idea, not the individual, which I think is essential as a product leader, because you. Your job is to move a metric. And to achieve these goals is not to be right. It is to make sure that collectively, we all achieve the results that we set out to do. And I've got. I've got a handful of product managers on my team that are actively disagreeing with me, which I love. Um, and there's a handful that disagree, but I need to pull it out of them, and that's fine too. You just need to know who those people are and how you can show up in a way that gives everyone else permission to jump in and tell you when you're wrong, tell you when you're right, in order to help move the product in the right direction.
Speaker A: Yeah, it's interesting. I liken it a lot when I think about leadership. Uh, it sounds really. It's infantilizing the team a tiny bit, which I don't usually like to do. But, you know, when you're teaching a child to tie their shoes, you don't just put their shoe on and go figure it out. If you show them how to tie their shoe, they try. You fix things, you show them again. And I like to set up structures that allow people to try out things, try out their courage on me, because I'm fucking safe. Ah. So if you say to me like, I don't agree, Start there. Don't start with the CEO.
Speaker C: Yeah. Right.
Speaker A: Don't walk into the boardroom and be like, you guys are all dumb and here's what we're gonna do. Start by disagreeing with me. Right. Start by challenging me or each other in a safe space and practice that so that when you do show up to say, listen, buddy, you're not right. I know this is your company, but you're not right. You've got a little something under your belt that you can have a narrative and a practice. Right. Um, because I think a lot of what we're talking about. I agree that people don't like change. And I actually am somebody who doesn't mind change. I'm very used to just sort of walk through life going, oh, that'll change.
Speaker C: Right.
Speaker A: But part of the way that I get people to change with me is that I show up like this. Yeah, I know you're uncomfortable, right? It's terrible. Like, I try to make it a little bit lighter. Like, I know, isn't it the worst? Just, I'm with you, let's go do that. If you show up with a little lightness, a little bit of like, I see you and it's hard, but we're still doing this. And people tend to be like, ah, this is the worst. But she's making it fun, right? So she's laughing while making us change. I think it's important. I think that connection piece is so critical.
Speaker B: Building on that. A way to build really high trust and connection with your teams is by being vulnerable with them. And there's a line that I'm, I'm working to figure out where that line is of being too vulnerable with being not vulnerable enough. Where you don't want to. You don't want to disclose every secret that you shouldn't be telling everybody. But I think there's some of it you should be telling the team and you should also be okay to tell your opinion on things. When you don't agree with certain directions, it can be, hey, I don't agree that this choice was made and this is the decision, here's how we're going to move forward, that's what we're going to do. And that builds a really high level of empathy with the team. And I know from my own team, I've, I've been working on being very vulnerable with them in 2025. And I've. From my perception, it's been perceived very well and they've been able to respond really effectively to me and they have more trust in me and I have more trust in them as a result. It's hard to do, but I think it's a really key skill.
Speaker C: Yeah, I like it. I think there's a, ah, um, I think that. So we've been talking a lot about, like, letting everybody argue and disagree and vulnerability. And so I'm, I'm a huge fan of vulnerability. I'm pretty much what you see is what you get. There's not a lot of secret, hidden depths. I'd make a terrible spy. We are. We already checked that box poker player. Exactly um, but at the same time, like, it's not a democracy.
Speaker A: Right.
Speaker C: So we can disagree and we can debate ideas. Um, but there is a direction that has been set largely. Um, and we can propose new directions and we can do different things. But none of this is a democracy. Like, at some stage we got to knuckle down and get some stuff done. So I love the idea of debate. How do you balance that with sometimes expediency of getting stuff done and moving?
Speaker B: I think it's critical to, uh, time box those debates and those conversations. I've seen success in doing that. Whether that's 30, 60 minutes a week, I don't know, depends on what the, the, the gravity of that decision that's being made. But you need to afford a platform for everybody that should have an opinion to express that opinion and acknowledging when that time is over. Um, because at that point we're just spinning and spinning and spinning. And I've, I've been on both sides of this where I've let things spin for too long. I've been on the other side where it's like I've made a decision quick, very quickly, and maybe didn't include people enough. Both of those are problematic in their own regard. But when you're able to meet somewhere in the middle, where you provide that platform, let people chime in and say, okay, I've heard you. Here's what you said, here's what we're doing, and here's what we're not doing as a result, being explicit and playing that back to people. At the end of the day, I think most people just want to be heard. So if you've acknowledged their point and gone in a different direction, that is 99.99% of the time. That's been fine for me because people just want a seat at the table.
Speaker C: Yeah.
Speaker B: So if you can acknowledge and create those breadcrumbs that indicate your point of view to here's how the decision was made, that has, that has gone a long way for me in terms of being quick while also being inclusive.
Speaker C: I think there's also this, like, feedback loop in my head on this conversation to bravery. Because I'm not always saying that I'm the person that has to make the decision. Like sometimes I'm saying junior product manager over there is the decision rights holder. Uh, and we're all going to give her or him our opinion, and then, my friend, you got to make a decision and we're going to run. And that's like this terror moment for some people. When they're like, oh, I don't know. And, and it's just like, you, you know what? You got this. This is the job. Right. This is the, this is the first big, scary decision of thousands that you're going to come across in your career. I trust you to make the right decision. And if. And if you're wrong, I trust you to learn quickly.
Speaker A: Yeah.
Speaker C: Go well.
Speaker A: And I think there's a.
Speaker B: So.
Speaker A: And then we need to move on to the speed, to the lightning round. But I just, I, I. What you just said really, um, resonates with me. I think it's a combination of very publicly saying, this is this person's decision, and I'm going to go with whatever they decide. And then behind the scenes saying, if you're wrong, I won't make you walk alone. Yeah, right. You will be wrong. I will be wrong with you. Right. So even if you make this decision and it's wrong, I will take the hit. When the time comes, I'll be like, yep, we got that one wrong. And that's that, uh, this is why we made the decision. These are the consequences. Hit me with it. Right. I think for. Especially for our younger people in the team that are learning, they need to know they're not alone, but that you will absolutely stand, take that one step back, and be like, here you go. I have your back. Right?
Speaker C: Yeah.
Speaker A: And there is a trust element there that I think is huge, that has to be built.
Speaker B: Most decisions aren't as big a deal as they seem in your head as well.
Speaker A: Exactly. We'll undo it. That's what I always say. Ah, we'll do this and then we'll undo it.
Speaker B: Software is the best because you can pretty much walk anything back pretty quickly.
Speaker A: Exactly. Exactly. All right, lightning round. Are you ready? Step one, question one. Um, you. You said at the beginning that you come from a long line of educators. Who was your favorite teacher and why?
Speaker B: I'm gonna, I'm gonna take some liberties on with this one. A specific coach, uh, that comes to mind is one of my former baseball coaches, Matt, who really honed in on, on kind of these fundamentals for me. And he had this saying, never pray for rain. Meaning always be prepared, no matter the situation.
Speaker A: Yes. I love it.
Speaker C: Wow. I'm stealing that one, too. Never play for rain.
Speaker A: That's a good one.
Speaker C: Wow. I mean, I'm just gonna, like. I feel like I'm a broken record, Leah. My favorite educator is BJ Foggy, and I just, like, really fell into this whole love of human Behavior design and, you know, testing the psychology of ideas before you build from him. Yeah.
Speaker A: Yeah, I love that. Um, I'm gonna go pretty old school. My favorite teacher was, um, my first grade teacher. Her name was Mrs. Arlen. She has passed R.I.P. Mrs. Arlan. Um, and I think when I. It. The way that it ties to what we're talking about for me is I was. I grew up in a really chaotic home, Very chaotic home. And she was one of the first people in my life who saw me, really saw me, and was like, this kid's got some space to fly. Let's get everything out of her way. Like, she just made space and was like, I'm gonna give you more room and more room and more, you know, I ended up. I was in her class for half the year, did second grade for the second half of the year, and then went straight to third grade.
Speaker C: Wow.
Speaker A: And she made that happen because she's like, I can't keep up with this kid. And someone else would have let me flail. Right. And just be bored and annoying.
Speaker C: Right.
Speaker A: But she was like, I'm gonna. I'm gonna load this one up. And so when I think about that, I often think we're all just that six or seven year old, hoping someone will see us for what we have, what we could do. And so when I lead, when we build, I'm like, all right, let me find the one who can do this.
Speaker C: Right.
Speaker A: Um, so I think that, for me, is such a huge part of what we do. So.
Speaker B: Yeah, that's nice.
Speaker A: Yeah. Um, okay, one more lightning round, and then we're gonna move on because we're out of time.
Speaker B: Um,
Speaker A: what is something that makes you feel brave? Like, when you. When you take a, uh. When you take a step, what makes you feel courageous or brave or is a sign of bravery? I guess.
Speaker C: I can go first if you want thinking time.
Speaker B: No, I'm. I'm ready. A sign of bravery is. Is what I was just doing, is just taking a second and being quiet and gathering yourself. So, um, I. I've recently taken on a coach, and we've talked about, like, the power of the pause, and there's different flavors of pauses. And I think taking that minute to yourself without explaining why are you doing this to other people is a way of reclaiming the narrative for yourself. And I think that's a really brave step as you are making critical product decisions, responding to a really hard question from a leader. If you just take that moment, you're saying, I got this, and it positions you better to respond. So something I'm trying to incorporate more effectively into my practice. I think I did it successfully in this moment right now. So more practice to be done. But I feel good about the journey I'm on there.
Speaker C: I love it. So there's a, um. There's a. There's a lawyer on Instagram. Now I'm going to share all my, like, weird, personal things. There's a lawyer on Instagram who does these. Like, try that and follow me. Um, and he talks about the pause and how to reclaim power in conversations. So, um, I will find that.
Speaker A: Wrote that book that you and I read. Yes. Yeah. Um, anyway, something about not arguing. Stop arguing. Do something. I don't know.
Speaker C: I'll have to look at it.
Speaker B: Send me the book. I want to know what it is.
Speaker C: Okay. But his Instagram is spectacular. Like, I don't like. Um, okay, I'll find it and I'll send it to you. Um, for me, I think there's a, um. There's a couple of elements of bravery, and the first is really trying to figure out why you're doing something. Um, and that's sort of been that, like, what's. What's motivating me. Oh, yeah, that's it. Jefferson Fisher, the next conversation. You need to read this book. It's awesome. Uh, are you. Less talk more. And it's. Instagram is off the hook.
Speaker A: Yeah, sorry.
Speaker B: Sorry.
Speaker A: I mean, interruption. I just realized I was right by me. I'm like, wait a minute.
Speaker C: I love it. Yeah. No, huge fan. I just love him. Um, huge fan. Um, so there is an element. So, like, there's been a couple of key moments in my life that have taught me that I'm not going to die, um, if I try something scary. The first was, um. Uh, I was in college. Um, and, uh, the subject matter I was studying was interesting, and I was good, but I wasn't great and I wasn't loving it. Um, and then, you know, sort of, like, things happened, and, you know, McDonnell Douglas and Garrett were sort of shutting down some of their fluid dynamics work. When, you know, when you're talking about building aircraft engines and. And people that were way smarter than me were getting shitty jobs, like designing stuff that I had no interest in. Um, and I had this huge crisis moment of, like, I didn't know who I was anymore, didn't want to do that. It's not where I wanted to go in my life. And so I sold everything I owned. Um, I dropped out of college. I don't like to tell people I Never finished college. But there's another scary moment for me. I'm just going to tell the no people that listen to our podcast.
Speaker A: Um, I have several extra useless degrees so we can balance out perfect.
Speaker C: I'll just share with you. Um, I mean I've done a lot of learning since then, but I just. I like dropped it all and went like, I don't know who I am and I need a minute to go figure it out. I bought a shitty VW van. Um, I loaded all my stuff in it and I moved to Tahoe to work at a ski resort to just snowboard. Um, and that led to like. That led to five years of traveling the world and being like, I. Like I learned to that I could live out of a backpack for five years. Like, I didn't own anything. Like, everything I had was mobile. I could survive a lot of these things. But I cried the whole drive from Arizona to Tahoe. My car broke down in the middle of freaking nowhere Nevada on a Sunday night. Like, I ended up fixing it with a screwdriver. With a screwdriver that I found in the back of my van. Like, bawling. I get up to like the last 30 minute part of the drive. It's snowing, the car skidding all over the place. Like, again, I'm um, like bawling my eyes out. There's no room at this, like one last hotel and it was too scary to drive. And I like, like I just sat there and freaked out. The fact like, but I survived. I got a room. Um, I Like there's a bunch of stuff you can survive. When it really comes down to. I think it's made me a lot more brave than just trying new things. Like, I'm probably not gonna die.
Speaker A: Not today from that.
Speaker C: Not today. And then to that sort of pattern repeats itself. Like, yeah, I don't know. I've. Like, I kind of did commerce. Um, and then maybe it's time to try a new industry. Right? Maybe financial services is like super cool. Maybe healthcare bio like pharma is amazing. And um, there's just these moments that have led to like repeated bravery for me. Um, and I would just say if it scares you, it's probably the right thing to do.
Speaker A: Absolutely.
Speaker C: 100. How about you, my friend?
Speaker A: Yeah, I, I would say. I mean I think moving around the world and country after country has been pretty brave. On everybody's always like, you're so brave. And I'm all, after we do it once, you're pretty much like, yeah, whatever, I can move anywhere I moved from Seattle to Sweden. I'm good. I can do almost anything. But I would say, um, there is some part of me that, uh, just recognizes the moment when conflict is coming and I could just m. Lay back and not engage.
Speaker C: Yeah.
Speaker A: And instead I go, no, I'm going to say the hard thing. I'm going to say the thing that's going to make the other person annoyed. I'm going to say the thing that's going to start the fight. And when I do that, as much as I'm like, I don't want to, it usually is the right thing to do. Yeah. Instead of not saying the thing, usually saying the thing is the thing that needs to happen. It requires just this little extra bit of courage. Um, so that's why I always say courage is not the absence of fear. If you weren't afraid, you wouldn't encourage. You just do a thing. And so don't you.
Speaker B: Don't you feel better when you say the thing, too?
Speaker A: Yes, always.
Speaker B: It's like a relief sometimes.
Speaker A: I'm like, I have now opened a giant can of worms.
Speaker C: Right.
Speaker A: And now we have to deal with it. But I always am glad, like, well, at least I said it. It's in the open in my head.
Speaker C: Because, uh, usually in those situations when I've seen you do that, Leah, everybody freaking knows.
Speaker B: Everybody knows.
Speaker C: And they're just not telling the, like, two or three guys at the top that are like, why isn't anything working? And it's like, because we didn't do the thing.
Speaker A: We didn't do the thing and we didn't talk about it. So.
Speaker C: Yeah.
Speaker A: Awesome. Uh, well, we're out of time, but, Steve, thank you so much for coming and talking to us. This was so much fun.
Speaker B: Thank you for having me. It was a. It was a pleasure.
Speaker A: Yeah, it was really fun. Thanks for sharing with us. It always goes so fast.
Speaker B: Yeah, it was great.
Speaker C: Awesome.
Speaker A: Uh, well, thanks for joining us. And then we will see everyone in the next episode. Bye.
Speaker B: Bye, everyone. Thank you,
Speaker A: Sam.
Other episodes covering the same guests and topics, from across The B2B Podcast Index.