YouSaid · the spoken record

Matt LeMay

lines on the record: 112
first: 2025-08-14
most recent: 2025-08-14
sittings or episodes: 1
sources: podcast

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“Money is how the impact of most teams is going to be measured. And if you don't have a point of view on why your team is a good investment either in the money return it brings or in another return that is equally or more important to the business, then again, that feels like a tenuous and risky position to be in.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“And we had to have a really interesting conversation around which one actually matters to our investors. And we kind of wound up developing these two scenarios, the high growth scenario and the low growth scenario, and talking to the product team, it was really clear that there was like no way they were going to hit the high growth scenario. So they pivoted to focus on profitability so they could build more runway and raise that next round as a smaller business with a sustainable revenue base. I get why people are hesitant to commit to revenue goals. I think that there are certainly situations where revenue goals would be too broad or not exactly what the business needs. But at the end of the day,”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“You know, I think, again, it depends. I know people have very strong opinions about teams should always or should never have revenue-based goals. I don't think it's that simple. I think sometimes, yes, if your company is working towards revenue, having a revenue-based goal makes sense, or at least being able to put some value in terms of revenue on the work that your team is doing. I've worked with some startups where they actively are not going after revenue because right now the name of the game is growth, right? They want to show that they have enough users to. Raise that next round of investment. I actually worked with one startup where their revenue was going up and their number of users was going up.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“What are your other OKRs? Show us the deck. They got it. And that gave them so much leeway to make bolder decisions, to work more closely with other teams, to ask for the resources they needed. And that process of arriving at that goal, that goal that is impactful and specific and one step away from what the company cares about the most is probably the most valuable way I have spent my time with teams of late because once you get to that you see how everything else flows from there.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“We know how much higher? And they said, Yeah, we actually have a number on that. I was like, wow. So if we had a goal of converting a certain number of single product users to multiproduct users, we know exactly how much revenue is on the line. And we're like, yeah, I guess so. So we were able to set a goal. And from there, we had this conversation about, you know, what's the number we would need to hit to make this team feel like a good investment. And we came to a specific number, and that number informed every decision that was made by that team for the rest of the year. We said by the end of the year, we need to convert this many single product users to multiproduct users because if we do that, there's this much additional revenue which contributes this much to the company's top line revenue goal. It's one step away. And when they went and shared that goal with company leadership, they got it right away. They didn't have to say, well, why is this valuable? They didn't have to say,”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“What framework should we use? How should we do this? And I was not asking very good questions. I was kind of panicking too, to be honest. And then I asked them, I was like, okay, why does this team exist? Why are we doing this at all? Like, why is the business investing in this big team to build all these features? Why do we care if we're a single product company or a multi-product platform company? And one of the team leaders said, oh, well, actually, the customer lifetime value of a multi-product user is much higher than that of a single product user. I was like, oh.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“And the business would say, Go build this, they build it, they'd celebrate, they'd say, go build this, they'd build it, they'd celebrate. And then the business said, okay, we're going to do things a little bit differently now. Now we have this top line revenue target. We want to make this much more money next year. And we want you to tell us how you're going to contribute to this. This was a really challenging conversation for this team because as much as people complain about being feature factories, again, it feels safer, right? There's more control over that. If you're told what to build, you have a lot more control over whether or not you build it than you do over whether or not it generates revenue. So we started having this conversation”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“But in that book, she has this visual where she says that most companies approach cascading OK as She has a visual that she compares that to which is like the company goal as a center of gravity and then every other team goal orbiting one level around it and this blew my mind when I saw it for the first time because whether you're doing okays or KPIs or North Star metrics, whatever framework you're ostensibly using, if you use it well, it looks like that. I worked with a team a while ago that was a traditional feature team at a fintech company. They were the team that was kind of like the team I worked with at MailChimp kind of given new features to build to take this product and build it more into a multi-product platform.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so the first step, and I think the most important and where a lot of my work plays out is in setting team goals close to company goals, no more than one step away from company goals. This idea comes from Christina Woodka's book, Radical Focus. She had a great episode on your podcast, but I just rewatched for inspiration before I came on here.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“What I'm actually saying. Is that the things you think you're fighting against are usually the things that are giving your work shape if you let them be?”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“These things are constraints, but they are the constraints that shape the work that we do. And if we embrace them as such, if we treat them as guides, not restrictions, if we say like, we're working with, not against the commercial realities of our business, there's so much we can do. There's so much that product managers and product owners and project managers that everybody working on product at every organization can do if we again work with, not against the realities of the companies we work for.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“Search engine, which is not going to happen. But the other way of looking at it is that those constraints. How you do product management, those are what guides you to the commercial decisions you should be making. If you're regulated, your competitors are regulated too. If you can really understand those constraints, figure out how to work well within them, that's a huge commercial advantage for your business. If you're B2B, I honestly prefer working with B2B companies in a lot of situations because they have such immediate access to their customers and they can understand the whole system of their customers and their users and how these things connect in a way that's really immediate and actionable. Similarly, if your company has quarterly financial targets to hit, congratulations. You know what the business really cares about. You don't have to go looking much farther than that. You don't necessarily need Dick cascade that 10 different levels into 45 OKRs if you can do work that you know feeds directly into what the company cares about the most. So yeah.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I mean, the reality is that most companies and product managers work at aren't big tech companies. And when I work with product teams at those companies, at insurance companies or at banks or at CPG companies, or I worked with a company a while ago that makes audio equipment, which was obviously really fun for me, the first thing they usually tell me is, well, you know, we can't do product the right way because we're a regulated industry or because we're B2B or because we have these quarterly earnings targets we need to hit. And that always makes me a little sad because yes, there's a way of looking at it where you can say, all right, if these five famous companies do product management the right way, then anything that puts us in a different situation from those companies must mean that we're doing product management the wrong way, which is demoralizing and distressing and again leads people to these kind of quixotic battles of like, I have to turn a bank into a”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“The business model works, what that value exchange is, what value is being delivered, what value is being extracted. That, I think, puts you in a better position to decide if I were to help the company achieve success, do I feel good about that? Do I feel like this is a company that if it achieves its goals, has made the world a better place or not? And the more you understand the business model, the better equipped you are to make those decisions with all the information available to you, I think.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“I think you touched on something really important there, which is that when you understand the business model, you understand the real world ethics and priorities of the company you work for, right? If you understand what the company's optimizing for, what they really care about, what trade-offs and sacrifices they're willing to make in order to achieve those goals, that tells you a lot more than the mission statement, which usually sounds great, but if you follow the money, if you follow the decision making, sometimes it paints a different picture. And I think the more you can understand.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“Does its own kind of harm, so I can't guarantee any kind of outcomes. I can say, yes, this will be received with generosity and grace in all cases. But I think it's the right thing to do.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“What is happening in the broader world, in the market, our product, we no longer believe we are on track to hit this, but we want to adjust so that the company at large can make better predictions and resource things accordingly. I don't know. But I think, again, if you are embracing that mindset that there are things outside of your control and your job is to do what you can from where you sit to contribute to the success of the business, I think you're certainly doing so much more by telling the business honestly what you think is possible. Stepping back from it and saying, like, oh, well, if we talk about it, we're going to get in trouble and nobody's going to believe us. And just that simple withholding of information.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“I hope so. You know, I'm always super again, it's outside of my control, right? I can't say, like, if you do these things, then you will be looked favorably, you will be looked upon favorably by the people who manage you because I don't know those people. And maybe they're not going to react well. Maybe they're not actually, you know, people are not always rational and these things don't always play out the way you hope they will. What I will say is there's a story in the book, an impact first product teams, about somebody who worked for a dating app and they were given a project to work on which had a very specific ambitious revenue goal. And at a certain point, it became clear that they were probably not going to be able to hit this because of other things they needed to do. So they went to the finance team and said, hey, we have to adjust this down. And the finance team said, yeah, of course you do. That makes sense. Let's adjust it down together. Would that conversation have played out the same way if they had not taken that step of saying proactively based on”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“Successful product. And then at the end of the day, you know, I'm not fighting my company to do product the right way. And if they can't do it the right way, I'm willing to die on this hill. It's like I work for a company. I don't get to make every decision. There are things outside of my control. I'll do the best I can. And I get to free up a little bit of energy to live the rest of my life.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“Internalize that, there's a real freedom in it. The thing that surprised me most when I was researching this book is that the commercially minded PMs I interviewed were also the happiest, which I did not expect at all. As you said, I come from a music background. I was expecting the business people to be really stressed out and like, I have to show up at work 92 hours a day to crush it and make sure that we hit the metrics and crush the numbers. But they were just like, yeah, I work for a business and I do the best I can. And then I go home. You know, when I'm at work, my job is to help the business succeed. And I do that by understanding our business model, by trying to do work that contributes to what the business wants in order to do that if my goals are really impact level goals. I have to learn about our customers, I have to do discovery, I have to do all these things that we're supposed to do, not because they're abstract best practices, but because that's how you build a”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“We are accountable for things outside of our control. The success of the businesses we work for. Is ultimately beyond our immediate control, and you can follow all the best practices and have the highest velocity and do everything quote unquote right. But if your company goes out of business, they're not going to say, yeah, we're going out of business, but we're going to keep writing your paycheck for two years because you, all of your OKRs were a 0.6 or a 0.7. That's not how it works. The reality is that things outside of our control affect us. And I think that if we can”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“Impact is not something we can just check off a list, right? If we're really working towards business impact, that means that there are things that might happen in the market that are going to affect us, right? Our competitors might launch something. There might be a pandemic or a war or something we didn't expect. We are reliant upon customers to change their behavior, to convert or to upgrade or to do whatever it is we hope they will do. I use the word hope because, again, we can do our best to influence that behavior, but we can't just check a box. And I think there is this very understandable human fear of being accountable for things that are beyond our control. I get that so hard. But what I think the last couple years have shown us is that”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“The funny thing is it's courage, but it's also a kind of radical acceptance of reality. There's a very kind of emotional philosophical dimension to this conversation because I think it is in human nature to not want to be accountable for things outside of our control.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“Made things easier. They did the kinds of things that are rarely celebrated in the way that traditional feature launches were celebrated. But because they had this clear, impactful, specific sense of what success looks like, they were able to take on that work themselves. Made the product better, made the business better, and it was just a great moment of working with a great team”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“Was a moment of silence where, again, for totally understandable reasons, people were like, Okay, you know, this is great. I see it, but like I'm kind of afraid that if we do this and this product manager, I will never forget that she looks around the room and she says, you know what, I am going to haunt all of you in your dreams if you do not take this on. This is the most important thing for the business. And everyone laughed. It was a strong comment, but it was a strong comment made in really good faith that in its own way, I think acknowledged the fear that people had about taking this on. She was like, look, this is really important. And if we work together, if we care less about the constraints and parameters and borders of our domains and care more about how we work together to deliver the thing that our leader has told us is the most important thing for the business, we can get this done. And they did get it done and they got it done through subtracting. They streamlined the experience. They took out steps that people were getting stuck on.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“Who really understood how important this was. She had worked on Hit the metrics we need to hit mindset. And she came to me and she was like, I want to make sure we do this because I'm worried about what will happen if we don't do this, right? I don't want to be on the product team that failed to deliver what matters most to the business. So she went and worked with some user researchers and found where people were getting stuck. She did this amazing study finding where people were getting stuck before they sent that first email. And she gathered together a group of product managers. I'll never forget this. I was on site in Atlanta. And she gathered together a group of product managers and she was like, look, these are the things we need to fix if we're going to hit this. But if we fix these things, I think we can do it. I think we can get there.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“To get value out of it. So she set a very clear goal for the product team. She wanted a specific change in the rate of users who successfully send their first email. She was like, as we build these new things, email is still where people are coming in. We want to make sure that they can do this successfully. And she set a really ambitious goal for the entire product organization. Put it forth to the product teams Lot of product teams were understandably hesitant to take this on for a number of reasons, right? They said, this is like, if we mess this up, that's the entire commercial heart of the business. That's really risky. Other ones, that's great, but we're building out these new parts of the platform that are really important. We don't want to risk slowing those things down. There was one product manager I worked with.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“So I was brought on shortly after they did a reorg. They went into a domains model. They had different teams that were supposed to be experts on different parts of this marketing platform that were building in new features. And their VP product, Natalia Williams, who then became their CPO, she said, this is great that we're doing this, but I'm worried that we're going to lose sight of the commercial fundamentals, right? We have these teams building this really cool stuff, and we've been so clear that we're excited about the teams that are working on initiative, that are building these new things, that are building out this platform. But let's make sure we stay focused on making sure that the entire platform grows in a healthy and sustainable way, and that as we are adding in these new features and functionalities, we're not making this so crowded and complicated that it's harder for people.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“It's funny. I worked with MailChimp for three years leading up to their acquisition by Intuit when they were on this really interesting journey of going from a single product company to a platform company, which is a journey that a lot of companies are on, right? Where they found success in one part of the market and they say, you know what, we recognize that there's a value add in working more horizontally and giving people a suite of tools they can use. We want to build these tools and really make sure that we are meeting the needs of our small and medium business customers.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“Being brave enough to look at their own work and look at what matters to the business and say, you know what, we are not going to incur the risk of being a low-impact team anymore. We are going to proactively seek out high impact work, and we're going to deliver even if it means we have to coordinate with a lot of other teams, even if it means that suddenly the executive team takes a really big interest in the work that we're doing. We're going to see that as signs of the work we're doing matters, not as things that are going to be an impediment to getting the work done.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“Thing and we need to make sure that we have all these layers and people are connected. We're doing dependency management. But as you add more of those things, it becomes harder and harder to do high impact work. The hood just gets heavier and heavier and heavier, which in turn sends teams deeper and deeper down the rabbit hole of low impact work. Low impact work begets low impact work. The more low impact work you do, the harder it is to do high impact work, the more likely you are to do low impact work, and so on and so forth. It goes and goes and goes until the next round of layoffs. And this is a real problem. I've experienced this at, again, pretty much every company I've worked with. And it's been really interesting to see how often the breaking of that cycle comes down to individual product teams.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“And that's exactly what happens in most product organizations. As you have more and more teams adding in these little features, making little enhancements, adding features which might get some usage, but they're not going to take away anything meaningful. They're not going to mess with the commercial engine of the business. You have more folks building in and the hood of the car gets heavier and heavier. The product gets more and more complicated. You have all these little bits that have little dependencies on each other and the product becomes, as I think most modern products are, a collection of loosely connected features rather than a single guided experience. What does that mean? That means internally building anything becomes a lot harder, right? Because there's 10 product teams that have to manage dependencies whenever you want to build something. So companies start adding program management layers. They're like, we have too many meetings. We need to reorg for program management because reorgs fix every”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“If you have the option of doing that or decking out the car with a pink job and rhinestones and making it look really, really cool, what are you going to choose to do? I know for me, I would choose the rhinestones every time, right? Because then the car runs however it runs. Whoever else is the expert in engines can fix the engine, but I'm going to do this thing, which everyone can see, all the executives can look at it and say, wow, look at how cool this car looks. And it's not going to do any harm, right? What's the worst that could happen? We can always take the paint off. Problem is, if you have 10 teams adding rhinestones to a car, eventually the hood of the car is going to be so heavy that you can't lift it to get to the engine anymore.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“The low impact death spiral is the dynamic in which every medium to large company I've ever worked with finds itself in one way or another. And honestly, a lot of small product companies do as well. And it goes something like this Starts with teams taking on low impact work, adding little features here and there, making little cosmetic improvements because it's easier, it invites less scrutiny, and you're less likely to mess up something important, right? The analogy I use sometimes is if you're working on a car, You put your hands in the engine, you might make the car run really well, or you might make it so that the car doesn't run at all.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“I don't think I've ever worked for a company where these things add up to a perfect breadcrumb trail. You can trace back from we prioritized these bits of work in this sprint because it adds up to this objective, which is part of this strategy, which adds up to this initiative, which is part of this bet, which will deliver this much impact. It's just not how things work in the real world.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“Maybe it's going to work, maybe it's not going to work. There are assumptions baked into each of those levels. You might go through the motions of doing OKRs the right way or doing strategy the right way, but that doesn't guarantee that your strategy is going to work. It doesn't mean that your OKRs are going to add up to what your investors or your shareholders need to see. So I think there's a tendency among product teams to really sweat the middle and to get really stressed out if the middle is not in perfect theoretical harmony with itself, if the objectives are a little out of line with the initiatives or a little out of line with the bets, are a little out of line with the domains. But at the end of the day,”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“You've actually spent so much time and energy being really clever and cascading these things into these intermediate steps that each step has incurred more and more risk that we might not achieve that impact we seek to drive. Each time we abstract things out, each time we cascade things from impact to something else until we wind up with a checklist of features to build, we're assuming that if we then build that checklist of features dot, dot, dot, we will have a successful business. But honestly, most of the companies and teams I work with, if I ask them how their lowest level goals add up to their highest level goals, they look at me like I just ask them the most impossible question in the world. Because by the time you get things down to that level,”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“Of product teams is to key to those middle pieces to say, okay, what we're doing is on strategy. What we're doing is part of objectives. We did OKRs right. We spent three weeks coming up with our OKRs for three months. It's OKR season, everybody. We have to pretend to care about our goals. And I read a book that says we have to have five to seven objectives with five to seven key results and we want the score of each one to be a 0.6 or a 0.7. And at the end of the day.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“Interesting. We live in a world where for the last 20 years of product development, we've been all about best practices. We love best practices. And I love best practices too. I think best practices can be really valuable, can be really useful. I love how much knowledge sharing there is out there. When I started 15 years ago, it was so much harder to get any sense of how anybody was doing anything. But I think the downside of this is that there are a lot of folks who are really, really fixated on doing things the right way. And a lot of the writing and thinking about doing things the right way exists in kind of this middle layer between impact and day-to-day work, right? So if you have impact, the overall success of the business, revenue, growth, profits, then from there you set objectives and you do initiatives and then you do bets and then you make a strategy and then you do your day-to-day work. I think the tendency among a lot of”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“That town hall day is like, okay, finally, I can just not have to deal with people emailing me every 10 seconds. It's a chance to take a deep breath and then get back to the stuff that really matters. But those top level things, those promises that have been made to the market at large, to the board, to the shareholders, those are often a great place to start for understanding what exactly your business is looking for. So you can figure out how your team's work helps contribute to success in the terms that matter most to the business.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“Best product managers and teams I've worked with are really curious to understand what success means to their particular business. So if that's a startup, how much runway do we have? What do we need to raise that next round? Are our investors looking for growth? Are they looking for profitability? What are they looking for in order for us to reach that next existential milestone? If we're a publicly traded company, what are investors looking for? What have we told shareholders? What's in our next perspectus? What are we saying we're going to deliver to the market at large? This information usually exists somewhere, but it's really easy to get disconnected from it as we go about the day-to-day work of doing product management. I've been in a lot of rooms having workshops and sessions with teams I work with where they're pulling up the last town hall meeting to look for slides from their CEO because they're so busy they have so many day-to-day things to deal with that for them.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, you know, my favorite definition of product management comes from Melissa Perry's book, Escaping the Build Trap, where she describes product management as facilitating a value exchange, right? You're facilitating a value exchange between a business and its customers. The actual shape and nature of that value exchange depends on so many things, right? It depends on your funding model. It depends on your business model. It depends on whether you're B2B or B2C. It depends on whether you're publicly traded or privately held. There are so many different variables that go into what a business expects from product teams. And one thing I've come to is that I'm probably too hesitant to generalize in general, aside from that generalization I just made. But I think that”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“So, if the product manager takes that on as their sole responsibility and says, I'm the mini CEO, I think about the business. That's a missed opportunity. In my consulting work, it's more often than not been an engineer who's actually able to get to that specific impact level goal for the team sometimes before the product manager does because the engineer is thinking in systems, is thinking about, okay, I know this system, I know this other system, I've had this conversation with this person. I think I see how this can all fit together. Sometimes it's a designer or a UX researcher who understands what customers need and who has that direct firsthand knowledge. So I think the way that I certainly initially misinterpreted the mini CEO thing was you are solely in charge of this as opposed to you are the person who brings that kind of CEO level commercial thinking to the team. And I've been much more inclined of late to see the product manager's job.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“I think the way I've come to think about it is that the product manager is responsible for the whole team thinking like a CEO, if that makes sense.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“Here's the ways to do this. It has taken me until writing this book to be convinced. I still feel like I need to be convinced a little bit sometimes.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“Would you invest in your team? And frankly, most of the people I ask that question to don't know the answer right away. They're not sure. They say, I think so. Or, yeah, yeah, yeah. And then you can see the gears turning. And again, to me, that is a risky situation to be in. Because if you can't answer that question as a member of the team, nobody else in the organization is going to be as well equipped to answer that question as you are. So bringing that question to the team, asking it and answering it proactively and collaboratively and being ready to say, okay, if we can't answer this confidently, what are the changes we need to make? Do we need to change our purview? Do we need to change our goals? Who do we need to talk to? What do we need to do in order to make this happen, in order to answer that question confidently, we are much better off having that conversation at the team level and waiting for someone else to have it.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“Righteous fact of the universe, right? My team would always be there for all time, and it was just a matter of us finding the next thing to work on, which meant, you know, doing discovery and making concessions to what leadership wanted and doing all that stakeholder management. But the idea that my team came at a cost to the business, that at some point somebody might look at my team on a spreadsheet and say, who are these very expensive people? Why do we need them? We actually need, it just wasn't something that crossed my mind because I wasn't in the room for those conversations. That wasn't how I was thinking about my team's work. So I like asking this question because it's a perspective shift. It gets you thinking if you were personally accountable for the existential market level success of this business.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“So, the first question I ask most of the teams I work with is, if you were the CEO of this company, would you fully fund your own team? And that is a small question that can provoke some big reactions. Because for me, when I was working as a product manager, I truly believed that my job was to find the next most defensible thing to build, build it, celebrate it, find the next most defensible thing to build, and so on and so forth, rinse and repeat forever and ever. I kind of assume that the existence of my team was this.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“I think there is a tendency, especially for those of us who do really thrive in that collaborative environment, who our nature is to not want to take credit for work that could only exist via the contributions of many people with diverse experiences and perspectives. It's really hard to say, like, well, I did this and I contributed to that. But that's part of why I wrote this book at the team level because I think for folks like myself who really enjoy and thrive in and enjoy that team environment, if you can look at the product team as the foundational unit of impact and say we delivered this, we were able to work together to have this impact for the business. That feels really good and also speaks directly to the work that that team did together.”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source
“Absolutely. Yeah, I mean, it's the most common resume advice I see, right? Is show the number, show the impact, say what you did. I have a friend who does resume coaching, and I showed her my resume a couple years ago. And she said, I love your resume except for one thing. Why do you write like a little girl? Say what you did. Say what your contributions were. Don't say, I helped. I may have maybe helped people do this. Say the impact. Put the number on it. And I think I needed to hear that because...”
2025-08-14 · Lenny's Podcast · The one question that saves product careers | Matt LeMay · IDENTIFIED FROM THE TRANSCRIPT · source