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A Conversation on Product Leadership


Episode 058

Matt LeMay is an internationally recognized product leader, author, and consultant who has worked with companies like Spotify, Audible, Mailchimp, and Google. He is the author of Agile for Everybody (O’Reilly Media, 2018) and Product Management in Practice (Second Edition O'Reilly Media, 2022), and has helped build and scale product management practices at companies ranging from early-stage startups to Fortune 500 enterprises. Matt is the creator of the One Page / One Hour Pledge, a commitment to minimize busywork and maximize collaboration that has been adopted by over 100 individuals and teams at Amazon, Walmart, CNN, BBVA, and more. Previously, Matt worked as Senior Product Manager at music startup Songza (acquired by Google), and Head of Consumer Product at Bitly. Matt is also a musician, recording engineer, and the author of a book about singer-songwriter Elliott Smith. You can learn more about his product work at https://mattlemay.com, and more about his music work at https://aquestionoffrequency.com.


 

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Episode Outline:

  • What makes a product leader role different from other leadership roles? 2:18

  • What makes a successful, empowered team? 5:43

  • The big mistake leaders make is not giving direction. 9:20

  • The number one characteristic of a bad product leader is the same characteristic that is likely to get someone promoted in most organizations 13:52

  • About the second edition of Product Management in Practice 25:00


Episode Transcript:


SUMMARY KEYWORDS

leaders, product, team, people, book, connective, product manager, work, empowered, second edition, matt, leadership, success, goals, leverage, promoted, system, management, folks, complexity


Intro (the incomparable Sandra Segrest) 00:03

Welcome to Product Voices, a podcast where we share valuable insights and useful resources. To help us all be great in product management. Visit the show's website to access the resources discussed on the show, find more information on our fabulous guests or to submit your product management question to be answered in our special q&a episodes. That's all at product voices.com. And be sure to subscribe to the podcast on your favorite platform. Now, here's our host, JJ Rorie, CEO of Great Product Management.


00:37

Hello, Welcome to Product Voices, I am so excited about today's episode, I've got a very special guest. And we're gonna be talking about a great subject that is very important to all of us, whether we're leaders, whether we're product managers, whether we want to become leaders, it is a very important topic for all of us. And that's leadership success, and how to set the right expectations and just kind of all things product leadership and what that means. So I have with me today, Matt LeMay. He is an internationally recognized product leader, author and consultant who has worked with companies like Spotify, audible MailChimp, and Google. He's the author of agile for everybody, and product management in practice, which is actually in its second edition now. He's helped to build and scale product management practices at companies ranging from early stage startups to Fortune 500 enterprises. Matt is also the creator of the one page one hour pledge a commitment to minimize busy work and maximize collaboration. It's been adopted by over 100 individuals and teams at Amazon, Walmart, CNN, and more. Previously, Matt worked as a Senior Product Manager at music startup songs up, which was acquired by Google. He was the head of consumer product at Bitly. He's also a musician, a recording engineer, and the author of a book about singer songwriter Elliott Smith. You learn more about him at Matt lemay.com. We'll share that on all of the websites as well. And you can also learn about his music work at a question of frequency.com. Matt, I am so excited for you to join me today. Thank you so much for being here.


Matt 02:18

Thank you so much, JJ, I am so happy to be here.


JJ 02:21

I don't know how you find the time to do all you do. But I love it. Because we're all We're all grateful for all of the awesome work you do.


Matt 02:29

Thank you.


JJ 02:30

So let's just kind of start the conversation with your perspective on what, what makes product leadership different from just general organizational leadership at large?


Matt 02:41

Yeah, that's a good one and a tough one. So in my experience, one of the most challenging things about product management in general, is that it tends to accumulate a lot of irreducible complexity, shall we say, because it's a connective role. You're not only having to connect the roles and the systems that you're working with, but also the actual human people you're working with. And nothing is more complex than people in a system. So being a product manager is hard enough, but I feel like as you become a product leader, all that complexity kind of levels up to you. So all the complexity of all the work that all the teams are doing and all the individuals who are looking to you for guidance, who have different styles, who have different teams, they need to work with, who have different goals and different fears, and different parts of the product or user journeys they're working towards. All of that levels up to a point where you as an individual need to find the points of leverage, where you can actually impact this system that is so incredibly complex, that you can never really have a handle on all at once. And that is a really, really, really challenging thing to do.


JJ 03:59

Yeah, well, I love how you you couch that it's a connective roll, right? I mean, I think is the thing that I find in product management. I've been doing this forever and I am lucky enough to talk to folks constantly on product voices and and elsewhere and you know, you kind of get the we get it but sometimes it takes like a phrase or a you know a certain way of wordsmithing it that kind of makes it resonate and that did it for me that connective roll it which is so right I mean it's like everything comes together and we've got to you know piece all that together and that's incredibly difficult. And you know, it's not that organizational or you know accounting leadership or sales leadership or marketing leadership or what have you isn't difficult, but product is just unique enough to make it you know that that much more difficult for leader so, I want to ask you something and I want to obviously I want to get to two how how do product leaders do it? Well, you know, in such a difficult environment. But I think I might want to start with something that I think might get us there. You know, we've talked a lot about empower teams over the last, what 5, 6, 7 years. I mean, and I get it, right. I mean, it's empowered teams is a great goal. You know, it's a kind of like I just said, it's, it's a good kind of wordsmith, easy way to, for people to understand. But let's talk about that. What does that mean? What what makes a team empowered, does it lead to, you know, a leader, a product leader, having, you know, more success, because their team's in power. So let's start there. Like before we dig in more, what makes a team, quote unquote, empowered?


Matt 05:48

The number one thing that makes a team empowered is knowing what success looks like for that team. And that is the piece that is missing in so many cases. If you read some of Marty Kagan's writing about empowered teams, if you read Christina wonky on empower teams, it's very clear from the folks who are really doing a lot of thinking and working on this idea that an empowered team isn't just a team that you leave to do whatever they want. An empowered team is a team that has a very clear and specific sense of what success looks like. And then is given the freedom and leeway to pursue all different avenues to achieve that success. So it's a team that knows, for example, that they're responsible for driving an X percent increase in the number of users converting through a specific experience, or a Y percent increase in revenue. And you know, attribution is really hard. These things are aren't as much as science. But teams that know, okay, this is what success looks like for us. And not only are we empowered to, but we have to pursue every different type of thing we can to achieve this goal. Where I think this falls down a lot is leaders who say, Okay, well, an empowered team is a team that I leave alone to figure out what to do. So I'm just going to stand back and tell this team, do whatever you think is right, and then come back to me and show me what you did. And inevitably, that fails. Because number one, that team literally does not know what success looks like. And when a team doesn't know what success looks like. They go from building what leaders want to guessing what leaders want. And that is a really, really dangerous dynamic, that I have seen play out time and time again, when leaders don't understand the amount of work and thought that goes into actually empowering a team. They just say, oh, you know, do what you want, I trust you. And that team immediately goes off and starts kind of asking around like, well, what does that leader want? What do they like, what's going to be the thing that's going to make them feel like they got what they wanted, this entire kind of shadow network starts developing where people don't actually feel empowered, they don't actually feel safe, because they have not been given an absolute specific. And, you know, I'm hesitant to use the word impartial, but at least kind of external to the leader themself vision of success, which they can work towards. And in the absence of that, I don't believe a team can ever really be empowered. I think a lot of these quote unquote, empowered teams are actually disconnected and insecure teams, and insecure teams are incapable of delivering good results.


JJ 08:20

You know, what I see so often in in teams and organizations that are trying to, like, impart this, you know, agency and in power their teams is they do what you mentioned, they just kind of say, okay, you know, I believe in you go do it, without any structure without any success criteria. And I think that's, I think that's actually more prevalent than than what we would like to see you go from kind of taskmasters to the other end of the spectrum. And it's got to be somewhere in the middle. So I think that's, I think that's spot on, and a really, really great way to say it.


JJ 08:57

So tell me about like, obviously, one of the the biggest mistakes a leader can make when they're trying to create empower teams is to not set those success criteria. But what else? Have you seen kind of as they're trying to create this environment and truly empower their teams to, you know, use their creativity, but to meet some specific goals? What other mistakes have you seen people make?


Matt 09:20

Yeah, so the other big mistake I see leaders making is that they leave teams to go off in a direction for too long without checking in with them. I think clear goals clear guardrails, which is to say being clear with teams about what you don't want to see or don't think will work. And short feedback loops are really key to good product leadership. And that short feedback loops piece is super important. So for example, you know, a lot of product leaders as hotel team, like go off and come up with a product strategy for me. Those teams inevitably panic, spend several hours googling what is a product strategy and put together like a 300 slide deck because they're so afraid of getting it wrong, but they just want to cover it every possible angle for what they think a product strategy is, when they bring it back to the leader, the leaders like, well, this isn't, and nobody's happy, nobody's happy with this.


Matt 10:10

The most effective product leaders I work with, say, Hey, I'd love for you to come up with a product strategy, I'd love for you to write a product brief, spend no more than an hour on it and bring it back to me and let's walk through it together. Product leaders are still people, product leaders still have a sense in their head of what they want, they still will be disappointed and will be confused if they ask for something and get back something that's very different from what they expected. And it's very hard to solve for that unless you have those shorter feedback loops. Unless you are checking in regularly and saying, is this what I expected? Or Is this not what I expected? Are we speaking the same language? Are we talking about the same thing? Are we not talking about the same thing, one of my first really bad experiences as a product manager, I had a leader tell me, I want you to put together a website for an API contest were running. And I was like, Oh, I'm going to do such a good job. And I go off and come up with this thing and come back. And when I come back with it's going to be perfect, and so impressive, and exactly what they want it went off for a week and worked so hard on this and came back on this product leader said, Man, this isn't what I asked you for at all. And I got so upset and so angry. And I was like, I worked so hard on this, how could you do this? And I'm like, You know what, I could have really saved all of us a lot of trouble by just going back an hour or so and being like, hey, is this what you had in mind? And I knew that not every product manager is going to do that. So I think the best leaders set that check in point proactively and say, Hey, don't spend too long on this before you run it by me not because I want to micromanage you, or because I want to say like, No, this isn't what I wanted. And what I want is perfect and best. But rather because we are humans, and we never know if we're talking about the same thing, until we have some tangible sense of what that thing is. So I think good product leaders are always working in those shorter feedback loops, to make sure that folks on their team are understanding what they asked for and to help them as leaders get better at asking for things at the right altitude in the right language in a way that's going to be as clear as possible to the folks they're working with, about what they expect and what success looks like.


JJ 12:21

Yeah, I love that. I think that's amazing. So I want to turn this a little bit differently. So so obviously, if if a leader because there's there's no person out there that I've ever met product leader who doesn't want to be good at their job, who doesn't want to be successful, right. And so by virtue of being in product, which we've already established is not an easy job. The folks who are in product are the folks who you know, like a challenge and, you know, are ambitious and want to be successful, for the most part, right? So nobody wants to be a bad product leader. But we've established a few things that we can do as product leaders to be good to be, you know, helpful to our team, etc. But sometimes it actually helps to, to be self reflective and look at ourselves and find the things that need improvement, right?


JJ 13:13

So let's let's talk about some things that kind of are indicative of a bad product leader. So if someone out there is listening, and they don't have to, you know, they do it themselves in kind of a self reflective manner. But if someone out there is listening, and they want to kind of say, okay, Am I successful? Or can I improve myself? What are some things that I could find in myself? That may be indicate that I'm not as good as I want to be? What are some things that you've seen that, you know, again, would characterize a quote unquote, bad or less than successful product leader?


Matt 13:52

So I have a hot take on this one. Okay, which is, the number one characteristic of a bad product leader is also the number one characteristic that is likely to get someone promoted in most organizations? Oh, which is that they say yes to what their boss wants, and then leave their team to deal with the fallout? Oh, yeah.


Matt 14:12

So there's a story I once heard about somebody who is a friend of mine who worked at a famous product company with a famous CEO. And there was a product director at this company, who managed to secure an audience with this famous CEO, and this famous CEO said, I love what your team is working on. Do you think you'd be able to get that shipped by next Tuesday? And this product director says, Absolutely, you got no worries. Next Tuesday, it's going to be out the door goes back to their team and says everybody cancel your weekend plans. Tell your families you love them, but you're not going to get to see them you're staying through the weekend is Death March time we are making this happen. And the team stayed through the weekend. A few people wound up having really non negligible serious mental health problems as a result of this And they got it done on Tuesday and wound up happening as a result of this.


Matt 15:05

Well, a lot of the best engineers on the team quit. People had against serious non negligible downturns in their mental health in their their lives as human people as a result of this. And can you guess what happened to this? Director?


JJ 15:23

Not good.


Matt 15:24

Got promoted.


JJ 15:25

Yeah, exactly. Not good. Not good to the to the team. But he loved it. Or she loved it. Yeah.


Matt 15:33

I've, I've been in that situation. You know, I think honestly, a lot of the way I got promoted early in my career was by saying yes to leadership, and then going back to my team and being like, there's nothing we can do. They're forcing us to do this. Those dastardly company leaders are making us stay for the weekend and get this thing launched on Monday rather than Thursday. It usually does not matter whether you ship this new feature on Monday or Thursday. And good product leaders always stay and trade offs. They never say yes, reflexively. They never say no reflexively either, they say, okay, great. Here's what the team is prioritizing. Here's what we're looking at. Here's what we'd have to do in order to make that happen. Do we deprioritize? This other thing, is this more important to the goals we're trying to achieve? And it's worth remembering that that famous CEO just said, Could you get this done on Tuesday? Now I demand that you get? And I've asked this question to rooms full of product managers before, if that product director had said, you know, I really appreciate that the team has been working at capacity, assuming we continue full time work and don't go over I believe we could get it done on Friday, or Monday, would that person have gotten promoted? Nobody's Sure. So I think, again, a good product leader is somebody who is willing to take on at least the tiniest bit of personal risk to respect and, you know, hold somewhat seriously the well being of their team. And unfortunately, those are not always the people who get promoted, which is how you wind up with, I think a lot of product leaders who get promoted really quickly, who kind of burn out by promising and promising and promising until they get to a point where they can no longer deliver on those promises. And they're kind of revealed as being people who've maybe gotten to where they are, by promising big things, but not necessarily getting to a place where what they're promising is sustainable, or healthy, for the actual realities of the team they're working with. Right?


JJ 17:42

Yeah, that's a really powerful story, actually. And, you know, one of the roles or responsibilities of a product leader in an organization, again, because it is a connective role, as you say, it's, is to educate the other leaders on how it works, right? And that there, it's not black and white, it's not Yes, or No, it's not, you know, Tuesday, or, you know, Tuesday at five, or, you know, the product fails, right? It's, it's that kind of, you know, trade off scenarios that we, that we live in, and work in and need to, you know, be good at. And so the better we are as product leaders, and educating the rest of our pure executive team and leadership team on how good product works, good product management works collectively, I think the better we are, but but, you know, there are a lot of business leaders out there that don't understand that right. In fact, most of them, I would argue, and so, you know, it's, it's somewhat understandable to, to be in that scenario, but I love how you've just kind of put it out there that, you know, that is not good for the long run. And it's certainly not good for your team. And there, that's a kind of a hard, hard choice for a lot of people, especially when they're at a certain kind of early stage, early ish stage in their career where, you know, again, we've established we are competitive, ambitious people had product and wanting to promote it. And that's, that's, you know, kind of selling your soul kind of situation. It's not easy to do.


Matt 19:16

Absolutely.


JJ 19:17

Yeah. So one of the things I want to ask and so, I love this story, and I love your hot take, as you said, because part of being a good product person and a product leader is kind of that self reflection, right? That that constant learning to constantly look at looking at yourself and say, Okay, I did I'm really strong here, but I still have some work to do here or like you said, You've done it too. I've done you know, things like that where I put my team on on the line when I shouldn't have and, you know, every every leaders look could look back and say I wish I would have done that differently. But it's it's a different thing to kind of come in from coming from scratch, if you will, right. So so an individual contributor or product manager or a lot A lot of us, you know, want to become product leaders and want to transition. And, you know, again, looking back on my career, I would have loved to have, you know, known what I know now back then, and been better as I progressed when we all have that. What would you? Yeah, right? And wouldn't that be amazing if we could do that? But what advice would you give? So there are a lot of people listening right now who are product managers, they have their individual contributors, they have ambitions to move up and get promoted in the right way, in a successful way, what advice do you give to people who want to move from ICs to leaders?


Matt 20:43

Yeah, I was talking to my friend, Ken Norton, who's one of my favorite thinkers and writers about product. And I love his answer to this, which was like, as you ascend into product leadership, you really have to think about leverage in a different way. It's not enough to just be in the problem solving the problem, you have to think about the steps you can take to solve the problem at a systems level. In other words, as that complexity increases, as you're responsible for more people and more parts of the product, and more goals and more outcomes, as the system grows in complexity, how do you find the points of highest leverage within that system? Because if you continue running around trying to put out every fire and make every decision and solve every problem, it's going to become unsustainable for you very, very, very quickly. And that question of, you know, what is the point of highest leverage here? What is the thing you can do that will have the most impact on this complex system? Is such a tough question to answer. And I think it also requires taking a step back and learning to kind of pick your battles and say, Okay, if I can move many parts of the system forward, but none of them wind up being perfect, or exactly what I think they should be, or exactly what I should should, or what do, I have made a greater impact on the system than if I really focus on one individual piece, and try to kind of polish it to perfection. So I think that ability to look at a system of ever increasing complexity and find points of leverage is really important. And in my experience, part of why I wound up doing things like this one page, one hour pledge, is that acting on those points of leverage requires subtraction more than addition, it requires really focusing in and saying, okay, given the complexity of the system and my role in the system, I can't just add stuff, I can't create more complexity in the system and add more things in, I need to really be able to find the shortest, most direct, most actionable, most accessible, clearest, most distilled and articulated way to have an effect on the system, which is part of why I'm such a big believer in time boxes, and I'm such a big believer in one pagers. I'm such a big believer, especially as one ascends into product leadership in these things that kind of force you into making a decision, having a point of view, deciding one thing, and not another thing. And I think that's where a lot of this stuff gets really, really interesting and really challenging. And we're again, you know, folks who have gotten to a point by just saying yes, and then equivocating, and stalling, have to learn a new way of relating, because if you want to have leverage in a complex system, you need to make decisions. You need to have clarity, you need to look at trade offs and decide to do one thing, not another thing when neither of those things are perfect. And it is very hard to do that. And it takes some courage. And it takes a lot of patience, and a lot of curiosity and a lot of listening and being willing to change your own perspective. And those are the qualities I see and good product leaders.


JJ 23:56

It's one of those things that you can't get right from day one, you can do Okay, from day one. But you can't be perfect, you can't be great. You learn along the way, you look back and you realize all the mistakes you made. Same thing, even if even if you're a great product manager, you're you're not starting from square one as a product leader, but you are looking at it from different perspectives and different leverage. So give yourself grace, but be very intentional about that. I love that.


JJ 24:23

So I want to talk a little bit about your your book, which is now in the second edition, their product management practice a real world guide to the key connective roll of the 21st century. Wow, that's like really impactful there. So tell me about tell me about kind of, you know, obviously it's in the second edition now tell me about what what led you to write the book but but also, you know, just kind of summarize for the folks out there who should go get the book by the way because you will learn a lot and kind of summarize the key things that they'll get out of this to become you know, better product people and better product leader.


Matt 25:00

Yeah, so I knew I wanted to write a book about product management. Because I felt like there was a book missing. I read a lot of the books about the theory of product management, you know how to put together a roadmap, how to do discovery versus delivery. And then once I got into most role, I was like, none of this, like, this all feels like such a mess. And I feel like I'm doing a bad job, because things are supposed to be this neat, orderly framework driven thing. And instead, it just feels like one emergency after another. And I feel like I'm a facilitator, not a visionary. And I'm having all these conversations with people. And I don't feel like I own the roadmap. I don't feel like I own anything.


Matt 25:44

And I started talking to more product managers on working with more product managers, and realizing that the people I liked working with the most of who I trusted the most were the people who took that more facilitative and connective approach, that the ability to bridge Theory and Practice is really important. And something that I wish I had received more guidance on when I started. So I remember having a conversation with a mentor of mine, he was like, Well, what do you want this book, to be?


Matt 26:13

Honest, honestly, I just want to dump out everything I think would be useful to a product manager in a book. And he was like, You can't do that. Like, you need to save something for that, like, that's too messy, that's not going to work, you have to save something for the second edition, or for another book. And I just remember in that moment being like, no, that's exactly what I need to do. I just want to it's so hard doing this job. And I want to literally just write a book, where I dump out everything that I think would be useful to a product manager. And that's the book, everything that I think would be useful, all the scenarios you might encounter, everything I think would be useful. And part of what was interesting about that was, you know, four years or so after the first edition was published in 2017. I was like, I know a lot more things that I think would be useful.


Matt 26:58

And some of the things I said before, I think are less useful, or are over simplified. You know, one of the things that's that's funny about writing a book is it fixes your perspective at a moment in time. And leading back over the first edition. There were certainly times where I was like, Gosh, I really oversimplify this. I think coming from a primarily startup experience when I wrote the first edition, I really over simplified, you know, using goals to make decisions, because in a bigger organization, you're going to have a lot of layers of goals that are in tension or in conflict with each other. What do you do that?


Matt 27:33

I think i i over simplified the idea of like, do the work you need to do no matter what, because people burnout, and that work gets applied unevenly to people in a way that's not particularly just particularly fair. So going into the second edition of the book, there were certainly things I wanted to sort of correct for as my own thinking had evolved and things I wanted to capture about the way that teams work in a remote or distributed environment about, again, the differences between working in a smaller company and a bigger company, lots of different things that I really wanted to keep in mind there. And I'm really grateful to the folks at O'Reilly for seeing the opportunity and given me a chance to update the book to incorporate a bunch of new stories from working product managers had to write something which I feel really speaks to the state of product management now, and is relevant and useful to product managers at this particular moment in time.


JJ 28:30

Well, it's a great book, and I highly recommend it for everyone. The first edition was amazing. Second Edition even better.


JJ 28:38

So Matt, thank you so much for joining me it has been a tremendous honor and a wonderful conversation. I very much enjoyed it. Matt LeMay thank you so much for sharing your wisdom and being on Product Voices.


Matt 28:52

Thank you so much for having me.


JJ 28:54

And thank you all for joining us on Product Voices. Hope to see you on the next episode.


Outro (the incomparable Sandra Segrest) 29:00

Thank you for listening to product voices hosted by JJ Rorie. To find more information on our guests resources discussed during the episode or to submit a question for our q&a episodes, visit the show's website product voices.com And be sure to subscribe to the podcast on your favorite platform.

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