Matt LeMay: Practical Wisdom, Business Impact, and Ethical Dilemmas in Product Management

Floating Questions welcomes Matt LeMay, a product leader, musician, and author of two books: Impact First Product Teams and Product Management in Practice. With experience at Spotify, Mailchimp, Bitly, and beyond, Matt shares his thoughts on navigating ethical dilemmas in big tech, driving real impact in product teams, and the essential traits of a great product manager.

Beyond work, we dive into his love for music, how therapy shaped his leadership, and the experiences that have shaped his approach to product management. Join us for a candid conversation on personal growth, career evolution, and finding balance in an ever-changing world.

Check out his latest book - Impact First Product Teams HERE

Transcript

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[00:00:00] 

Matt: Welcome to Floating Questions, the podcast where curiosity leads, we follow, and stories unfold. My name's Rae, simply asking questions. Shall we begin?

Rui: good evening, Matt.

Matt: Hello, Ray, how are you?

Rui: I am great. Um, I really couldn't imagine that I'm actually in this recording with you right now.

Rui: I read your book. it was recommended by a co worker. Sam, thank you very much, uh, for the recommendation. the book is called Product Management in Practice. for context, recently I transitioned into product management, from data science,

Rui: and your book gave me so much tips and I'm really, really grateful for that. I love your humor. I love the authenticity [00:01:00] that you have in the book.

Rui: and I'm just making a lot of notes that immediately become very practical guidance for me. So thank you very much for that. 

Matt: you're so welcome. I'm always really happy to hear when the book resonates with people. it's the book I wish I had had when I was transitioning into a product role myself. So it's always really gratifying to hear that folks have found it helpful.

Rui: Yeah, well, you find the product market fit. I am one of your audience Anyway, Maybe let's just get into a little bit self introduction

Matt: So I'm Matt, I wrote this book, Product Management in Practice, which is now in its second edition via O'Reilly. I got into product management by accident 15 years ago, as I think a lot of product people get into product management by accident. I had been a music writer and musician before that. I still moonlight as a musician.

Matt: I've actually got some of the records I worked on and shows I've played as kind of artifacts of another life behind me. I just finished my next book, [00:02:00] Impact First Product Teams. It's an interesting moment to be thinking about what it means to make sure that product teams are delivering impact for businesses while a number of businesses seem to find themselves in Positions of questionable ethics, especially in the big tech world right now um, so it's an interesting moment, I think to be doing this kind of product work 

Matt: and to be a human being living in the world trying to do their best.

Matt: So, really happy to be talking to you today.

Rui: Yeah, awesome. Maybe let's just talk a little bit more about A lot of companies find themselves in ethical dilemma, Is there a specific example that you have in mind that prompt you to think in that direction?

Matt: I mean, I think there are two ways you can look at it, right? One is kind of the obvious examples of technology companies that have taken questionable political stances that have, Comported themselves and whose leadership have comported [00:03:00] themselves in ways that I think run counter to the ethics of a lot of people who have worked for them.

Matt: I think there's also the broader question of, you know, We tend to operate within economic systems that privilege growth at all costs. And I think if you look at the state of the world right now, there's a very good question about, is growth at all costs a sustainable model? Is it helpful for ecosystems and humans and communities, or is it simply reinforcing existing disparities?

Matt: who are we ultimately serving when we build things and deliver things? I think it's a really important question to answer. Or at least a really important question to ask, I certainly am not going to pretend to have answers to any of these big macro level questions, but I think that for folks, especially folks who've worked in tech for a long time who kind of grew up through this utopian promise of tech being something that will make everybody's lives immeasurably better.

Matt: I think there is a [00:04:00] moment of kind of collective reflection happening in terms of Do we think that the things we're working on are delivering those promises? Are they making the world better? Are they making the world better for some people and worse for some people who is actually benefiting from the things that we build?

Matt: i've been really feeling that the kind of tension between that and this message that i'm writing about in terms of product teams being Aware of and contributing to business impact. So I think that's a challenging top of my intention for a lot of folks working in this industry at the minute.

Rui: There is a lot to unpack in what you just said, maybe company could either take stance. Uh, and make it extremely explicit about what is their political attitude, or they can choose, no position position, meaning like you just make it extremely apolitical, And focusing [00:05:00] on, the business model, the customer user experience, and building a product, right.

Rui: or maybe you don't really see that clean cut between these two camp. And if there is somewhat, difference between these two camp, which one would you prefer the company, to be, 

Matt: Yeah, no, it's it's a tough question. I think one thing i'm becoming more aware of And there are other folks in the product community who've been been saying this better than I have for a long time Uh, the business model is intrinsically political, right? I don't think there's any such thing as an apolitical business model like the question of where the money comes from who the money goes to whether the goal is, growth, whether the goal is sustainability, what compromises are willing to be made for what outcomes.

Matt: And I think As we see what the consolidation of technology in the hands of a small number of players who want to continue expanding their [00:06:00] share what that looks like that's intrinsically political you know, i'm doing a little bit of reflection personally where i'm like, I think I was much less critical of the power certain companies and people had when I ostensibly agreed with them politically.

Matt: and it's much more like, oh wait, but was that power always bad? Was this business model always going down a path that would inevitably have to do harm in order to achieve its own stated goals? And I'm really struggling with that to be honest. It's a really tough one.

Rui: Do you have a specific company in mind that you have a lot of very complicated feelings about?

Matt: Yeah, I mean, if you look at any big tech company, if you look at Meta, if you look at Amazon, if you look at Google, if you look at any enormous technology company, I use their products all the time. I use Instagram to look at videos of cute cats and keep in touch with my friends. I use Gmail for [00:07:00] everything.

Matt: I use these. Products ecosystems, but again, I feel like my experience as a user and the macro implications of the business model are at odds with each other in some ways and It's hard to reconcile that. I mean as a musician I use spotify but I recognize that spotify has Not had a great impact on the ability of artists to make a living It's a great business model for listeners in a sense, but it comes at the cost of providing sustainable impact to Artists the streaming model in general does that you know, I think spotify is always the easiest one to point out but it's not like apple music or Amazon music are an intrinsically more sustainable business model.

Matt: It's just an incrementally better payout for artists within a fundamentally unsustainable model. So I certainly feel the weight of being within [00:08:00] ecosystems that as a user I benefit from the very scale I think in a sense makes these companies worrisome to me it's a strange thing.

Matt: And how do you reconcile those things? In your day to day And then how do you reconcile those things as a product person, right? How do you contribute to the success of your business while also being able to acknowledge the trade offs that go into that success?

Matt: Um, that is really really hard to do 

Rui: uh, relate to that statement a lot because at one point I also got an offer from Robin hood. the intrinsic business model is that if you have transaction volume. the company get a very small cot, and then that's how you make money, right? But I believe in value investing so It goes against my belief to build an app to try to prompt people, especially People who probably don't really have that much financial literacy to [00:09:00] keep trading granted you can provide a lot educational material through that channel But at that point in time I was thinking how do I really feel about prompting people to do more trading?

Rui: When I inherently don't really believe in that Approach of investment. that's one of the reasons why I just, didn't take the offer and choose the company I'm working for right now.

Matt: I think you touched on something really important there, which is that you needed to understand the business model to understand the ethics of the company. and I think that's really key and part of why I encourage product people to really understand the business model of the companies they work for.

Matt: you know, The mission statement might say one thing but the business model might say something very very different And it's usually the business model that really gets to the ethical realities of the business you work for And I think empowers you to make decisions like the one you made where you can look at it and say Okay, I understand the ostensible [00:10:00] goals of this company as they wish to understand them being more positive but if you look at how they make money, I would be optimizing something that I don't believe should be optimized that way.

Matt: I would be optimizing something for an outcome that I don't believe is a just outcome. And I think it's really hard to know that and understand that unless you understand the business model of the business you're working for.

Rui: Yeah, absolutely. I love this articulation. 

Rui: that also ties to personal motivation at work too. Cause if you fundamentally feel agonized about a product, you probably also don't have that much motivation to really work for it 

Matt: Yeah, exactly. I think the reality of product work, and this is something I've been thinking about a lot, is that it is a business accountable role, right? You are ultimately accountable to driving the success of the business, to taking that business model and making it more effective in whatever way, whether that's by driving more volume or by reducing cost or whatever it is.

Matt: And if you fundamentally believe that the more effective the business model is, [00:11:00] the more harm is done in the world, then I don't think You can really do that job effectively, nor necessarily should you. So, the way I kind of framed it in this book is that understanding the business model is key to really knowing whether this is the kind of work you want to be doing.

Matt: I think it's fair to say the mission statement, the vision will almost always be some version of, we want to make the world a better place. There are very few companies that come out and say, We want to exploit ignorance to drive as much profit as possible for our shareholders Like we want to get people addicted to these like little dopamine hits so that they Drive more advertising revenue for us, even if it destroys their mental health That's not how the ceo opens the town hall.

Matt: I think if you look at the funding model too, that also tells you a lot about what you can expect, right? if a company has raised a whole lot of venture capital and has pressure to deliver at a certain way in a certain time frame, that's really important to [00:12:00] know.

Matt: If a company is, bootstrapped and Wants to grow more slowly and deliberately And grow in a way that's sustainable and profitable. That's also important to know These are really the critical pieces for understanding what success means to a business which you need if you're going to be a product manager because you are ultimately Evaluated on whether or not your team is contributing to the success of the business.

Rui: 100%. let me maybe throw a little bit curveball here. Um, don't you think anything that just keep growing bigger and bigger and more and more volume in general, anything that goes to one end of the extreme, ultimately will become something potentially evil and harmful.

Matt: I don't know I I think there are some businesses that i've seen and worked with that are You know delivering real value for people that aren't necessarily trying to like destroy all their competition or capture You know [00:13:00] an entirety of a market without any thought to their users and what's possible.

Matt: Certainly there are companies that have become horrifically terrifyingly big this is ostensibly why we have antitrust law, 

Matt: When checked and constrained by healthy well regulated market dynamics is not intrinsically evil But I think that once those checks and balances fall away And you have companies that are that have effectively limitless access to capital And can use that access to capital in whatever way they see fit it raises a lot of really Tough ethical dilemmas, especially when those companies can contribute to political campaigns and can influence the decisions made by the folks who whose job should be to Regulate and put those constraints on those companies to make sure that at the very least there are some opportunities in the market [00:14:00] for new players could be offering a better and Less growth obsessed approach to actually succeed.

Rui: I see. Interesting. Um, there is actually another question that I just had it in my mind. I just like completely blanked out for some reason. do you feel each book that you're writing it's almost like, um, an encapsulation of different stages of your product management career, like how, accumulation of the things.

Rui: Until that point in time, push you to the next stage of thinking. And have you noticed any big themes in your thinking and development along this 13 years of journey, as a product manager?

Matt: That's a great question. So product management and practice, the first edition came out in 2017 when I had spent about five years kind of working full time and then year or two working as a [00:15:00] consultant. Um, so I think it was really written from that place of just starting to feel confident in my approach and just starting to feel like I had figured it out.

Matt: The second edition, you know, I had spent more time working with more product managers and more teams. I think I had a kind of stronger opinion about some things. 

Matt: this new book, I think really came out of the last three years of consulting work for me, where so much of the time I spent with teams was about helping them understand what success looked like for the business and what success looked like for them and whether the things they were working on really stood any chance at all of delivering that success.

Matt: You know, I had worked with a lot of teams who Had been asking me about how do we do prioritization? What framework should we use? How do we do this? How do we do that? And then once I actually understood what the business expected of them, it was like, Oh, none of this matters. Like you're you're evaluating three different things all of which are going to deliver this like very tiny incremental value When the business has actually made a pretty huge investment in [00:16:00] this team and wants to see much more value than that so I hit this point where I realized that so much of the work I was doing was about reconnecting product teams with the impact of their work and 

Matt: you realize at a certain point that the conversations you've been having have certain themes and threads that run through them.

Matt: And then if you can take those threads and kind of weave them into something more self contained, then that's the goal. So hopefully that's what I did.

Rui: Yeah, that's great. Actually, when I was reading your book, product management in practice, a theme that stood out to me the most is humility, um, Keep your ego low, and also sometimes In order to do the right things, you need to do the hard things.

Matt: Yeah.

Rui: for example, it's easy to push. the last minute request on to, you know, this is something that come from the upper [00:17:00] management,

Matt: Got to do it. 

Rui: me, we're just going to have to do it.

Rui: that's the easy thing to do, but the right thing to do is to help the team really understand why we have to do this right now. I'm always curious the journey going to a point where that level of humility is present, that level of clarity is present.

Rui: do you do a lot of reflection in your personal time? Like, does the music really help you? 

Matt: Yeah, I mean, I think in a funny way, my music career humbled me before I even started working in tech. when I started my band, we were at university and in a very small world, we were very cool. But once we started. touring and playing real venues.

Matt: we were just Tuesday night's band playing to three people in a club in Omaha and, you know, begging for ten dollars for gas money to get to the next city. So I, I think one of the things you learn Pretty quickly is that if you want to grow you can't be comfortable and a [00:18:00] lot of people have said this again better than I have right that if you are Optimizing for a situation where you feel in control and you feel like you're the best and smartest You're probably not learning anything um I see a lot of product folks go through this when they're really good early on And then they get promoted and they really struggle because they were good at Sort of being that IC product manager and getting things done.

Matt: They got a reputation as the person who really does stuff. And then when they have to manage a team, they have no idea what they're doing. Um, I was lucky in a sense in that I was not very good when I started. Um, I really struggled a lot. I don't think I thought of myself as like a good product manager at first.

Matt: I think I thought of myself as a very bad product manager and I. Really struggled to understand why I wasn't doing a good job. The journey for me of writing product management and practice was largely a journey of acknowledging the mistakes I had made and reclaiming the things that I didn't think I had done well, but I had [00:19:00] actually done well.

Matt: Um, I think a lot of the communication pieces, a lot of the things where I didn't push my own vision, but helped synthesize some other people's visions, and help support other people at the time I was like, Oh, I'm not being a real product manager. I'm not owning the roadmap. I'm not pushing the vision.

Matt: But in retrospect, I was like, No, I was actually doing a pretty good job there. you know, if anything, the pattern I fell into that was easy for me was a pattern of self deprecation and not owning those decisions of going to the team and being like senior management is making us do this.

Matt: It's so hard to be us so unfair, rather than being like, Hey, this is really important to the business. Here's why we have to do it. Or going back to senior leadership and saying, cool, here's what we're working on. Here's how much capacity we have. If we need to do that, something else has to fall out. And what is it?

Matt: so I think for me, it was almost the other. Direction that felt really comfortable for me, where, I somewhat passive aggressively would just hide behind, Meh, I'm bad at this. I have no idea what I'm doing. there was [00:20:00] a moment that really stuck with me. Where I had been relying on that flavor of self deprecation a lot.

Matt: And I got an email from one of the engineers I work with that was like, Hey, are you doing okay? You seem really down on yourself.

Matt: Like, do you really think you're doing that bad a job? And I was annoyed. I was like, no, of course, I don't actually think I'm doing those. Oh, that's terrible. Like I'm manipulating this person. I'm Using self deprecation as a as a strategy to like get people not to challenge me on stuff Because i'm afraid that I can't step into that space And hold confident in what i'm asking people to do So that was a big part of the journey for me.

Matt: It was recognizing that, I wasn't actually helping anybody by being like, I'm terrible. it wasn't making anything better. I had to actually step into like, no, I need to really take this seriously. I need to stand in what i'm doing when i'm doing it. I need to be accountable to my team even if They're not going to be happy with me and there will be times when they're not happy with [00:21:00] me.

Rui: Yeah, sometimes I experience similar thinking or feeling the self deprecation is also another way to crave for recognition

Rui: and 

Matt: Yep

Rui: for validation. You want other people to almost like prop you up

Matt: Right. You want to be like, Oh no, you're doing great. And it's like, Oh, I am. Oh, I didn't know, but like, yeah, it's really hard to let that go. but I needed to, to 

Matt: get to the next level. 

Matt: I think one of the really tough lessons I learned along the way was that in my attempt to, get my team to Like me I had kind of cast the business itself as a common enemy Business is what pays all of our bills like the business is The entity that we collectively work for and a lot of the folks who are giving us things to do Know things that we don't know and have information that we don't have so I think I did nobody any favors by Attempting to protect my team from the business that they actually work for it turns out that Doesn't actually help very much.

Rui: Yeah, so far we [00:22:00] talked quite a bit about how you have been trying to see your own ego and manage that and grow out of it. but everybody is at a different stage in this journey, right? So how do you manage others potentially, you know, problematic behaviors or ego?

Matt: It's really tough, I mean I've given a few talks about this in the last couple years, it's defensiveness that's driving a lot of this bad behavior You have a lot of people who are not bad people who are not bad product people But who are insecure and defensive and put up their armor and aren't listening and aren't reflecting I think A lot of product folks, especially a lot of product folks who Started in a kind of chaotic environment and got promoted a lot quickly, which was definitely me um kind of exist on this razor's edge between like I have no idea what i'm doing and I can't acknowledge that.

Matt: I don't know anything and I have to pretend like I know everything um, which is a really hard place to [00:23:00] be because on the one hand you're like I might be doing everything wrong, but on the other hand, it's like I can't admit that I'm doing anything wrong Because then the whole thing might come collapsing down around me and everyone might see that.

Matt: I don't know what i'm doing You know i've had the pleasure of working with a few product managers who've actually managed to turn themselves around there um, I don't think I was able to do it until I changed jobs, but i've worked with some product people who've Really, really impressed me with their ability to say like, woof.

Matt: Okay. this is real. I was beloved by senior leadership when I was a junior product manager. Cause I just worked really hard and got everything done. But now that I'm working as the lead of a team or with other teams, I can't do that anymore.

Matt: I can't just jump in and do everything myself. And that's where I see a lot of people fall down. Um, because it does require a different kind of humility and a different kind of openness and a different kind of, just way of relating to the world to an open exchange of information and to work with people rather than just [00:24:00] pushing stuff.

Rui: I see. what is your way to really get there besides those aha moments or things that just like hit you?

Matt: Yeah, I mean, therapy is a short answer. therapy for a really long time. I think over time, you start to get a better sense of what you're kind of default stress reactions are, you start to get a sense of the narratives in your head and the things that pull you out of touch with the reality of your situation.

Matt: I'm very hard on myself when I feel like I've made a mistake and I tend to dramatically overcorrect for that mistake rather than just letting it exist in the world. You know, when I was younger, I would try to convince people, like, that wasn't a mistake. It was actually the right thing, which was even worse, um, in a sense.

Matt: when I was working with my business partners in the States, I remember there were a few times where I would feel like I made a mistake and I would get so upset with myself and so angry at myself. I'm going to make such a big dramatic [00:25:00] show of overcorrecting it that one of my business partners eventually said, look, you've made this a lot worse.

Matt: Like, I barely noticed the mistake you made, but now we're all dragged into this like mellow drama like, you're making it worse. I was like, Oh no, my old coping mechanism is not working anymore. What am I going to do? I had a therapist in New York who basically told me.

Matt: Part of what you're trying to do is create a little pause, a little space before your unregulated reaction to something, you know, one of the pieces of advice I give in, in product management and practice is if you're having a difficult conversation, just take a moment to like, okay, great, like, give yourself a little buffer, just that little moment.

Matt: So you don't blurt out the defensive reaction or the unregulated reaction, or, you know, for me, it tends to be a lot of like, well, I'm trying really hard. Why are you being unfair to me? Which is not helpful to anybody. so again, I think a lot of it has been working with, good therapists, we're having, people in my life who can reflect those things [00:26:00] back to me.

Matt: Um, building partnerships with people and teams Ways I have worked in the past that are no longer serving me are revealed to me as such. And I work with people who can help reflect that back and help me, you know, get to that next level, whatever that is.

Rui: That's great. And sometimes it's kind of interesting to think about the co worker. Maybe you have so much problem with today my actually end up being a very different person a few years down the road

Matt: Yeah.

Rui: you know with the time people morph and change and sometimes when we're not super good at certain job at certain time maybe Sorry, like, just at that point in time that we're not the best version we could be.

Rui: I mean, we were the best version we could be at that point in time. It's just not the better version that we could be in the future. potentially people just really need that space and [00:27:00] time to grow.

Matt: And I think you need to make mistakes. I think that's one of the challenging things about You know, one of the things I tell the product managers I coach is like, you will make mistakes that will have a real negative impact on the people you work with and the business you work for. That is an unavoidable part of this job and to whatever extent you can be emotionally prepared for that, be emotionally prepared for that, because that will happen.

Matt: It's not a question of if it's a question of when and how much Um, so it's really important to prepare people for the fact that there's no perfect way to do this job There's no way to do this job that will mean you made the right choice every time Um, there'll be a lot of times where there is no clear right choice And the more you try to defend or insist that it was the right choice The more information you're taking off the table that should probably be on the table it's, you know, emotionally challenging work in a lot of ways because you're facilitating conversations and decision making among people who have a lot of [00:28:00] different personalities, beliefs, goals, needs, expertise.

Matt: I think, over time for me anyhow it's helped me be a little bit more reflective because I, I've had to be like I just couldn't do this job effectively if I hadn't worked on my own stress reactions to things and learn to put a little bit more space between. What's happening and how I perceive it in the moment.

Rui: Right. So to some extent, I would say if you really talk about what product management is, or who is a fit for this type of job, sometimes I'm thinking probably if you have the courage to really face yourself honestly and keep just growing as a person, that's the key to really unlock your career, 

Matt: Yeah, I mean, you're never gonna know everything you need to know to do a product job well. Like, you're gonna need to learn new things all the time. 

Matt: I showed up and I was like, I know some PHP, I'm technical. And I was working for a company that was not. Writing code and PHP and [00:29:00] people were like, who cares? can you solve these problems for us? Do you understand this? And it turned out for me that, my instinct was I don't want to look stupid.

Matt: I want to impress everybody. I want to be cool. but. It was always more helpful to learn in context from the people I work with. 

Matt: when I work with people who are like i'm not technical i'm like that's fine You don't have to be technical, but you have to be curious.

Rui: Well, at this point, we already talked about product management, for quite a bit. And honestly, not so much about product management, but rather the traits you need to develop in order to be a really good product manager. 

Rui: we can take a turn and maybe just talk a little bit more about, how did you really get into music and how does that really morph you as a person? impact your career besides the part that you already mentioned,

Matt: I grew up in New York City. And, you My best friend in high school, his dad was a music librarian at NYU, and he would take us to concerts all the time. [00:30:00] So I grew up just Totally head over heels in love with music going to, you know, the knitting factory downtown in New York, which was always all ages so we could get into shows there.

Matt: Going to other music which was a record store in New York and every Tuesday finding out what the new releases were writing about music, internet, you know, I wrote for pitchfork before anyone really knew what pitchfork was when it was just this like nerdy kind of niche indie rock website. I just loved being around.

Matt: I loved Being around music and being around musicians Um when I got to university I started a band and it was so thrilling for me to get to make music with people and one of the things you learn making music Which I think is very similar to product management is how to Align and motivate people who have skills that you don't have, right?

Matt: Like I couldn't play drums as well as our drummer. I couldn't play bass as well as our bassist. There were a lot of things I couldn't do in the same way that the people I was working with [00:31:00] could do them, but I had to figure out how to get us all aligned, how to get us on the same page, how to figure out what we were doing together.

Matt: Um, and I think that really helped me when I got into product management. Um, because I was comfortable working with people where I couldn't tell them exactly what to do, you know I couldn't get in there and say You know, especially when you get into more esoteric stuff like mastering engineers and people who were into really, you know very detailed audio decision making Like I could tell them at a high level what success looked like to me But I couldn't tell them what to do and I think Being experienced in that was really really really helpful to me as I moved into a product management role because I understood that I could help people understand and align on what we were working towards, even if I didn't understand and even if I couldn't control every facet of the work that they did.

Matt: Um, 

Rui: share a specific story that you still have in mind when you were trying to [00:32:00] play the band and there is a specific outcome that you were trying to like present.

Matt: So I remember one time we were working on a song for our second record and, you know, I had put together a lot of the demos and the early versions of these songs and I could tell that something wasn't working. Like something in this song just wasn't clicking. And I told my bandmates, I was like, go practice without me.

Matt: I want you to surprise me, like something's not working, but I've reached the limits of my ability to hear what should be going on here. Like, I'm stuck in my own understanding of what this song needs to be, and it's not working. So you guys go, practice, show me what you came up with, but I want you to just kind of do what you do if I wasn't, um, they changed the rhythm of the song.

Matt: in a sense, I think being locked into very like traditional rock rhythms was one of my big limitations as a songwriter. So, when the band got together, the dynamic was really different without me there. the way that they kind of went through this push and [00:33:00] pull of the different players, like who was leading, who was following, who was moving things in what direction, it came to something really different and it was great.

Matt: I came to the next practice and they showed me what they came up with and I was like, Yeah, it's perfect. but I think it was that ability to recognize the limits of my own perspective, and to say, like, I know this isn't doing what it needs to do, but I don't know what it needs to do. Like, I know that this isn't right, I don't know where to go from here, so show me where to go.

Matt: I wish I had done more of that, to be honest. But I think it was a good lesson for me, in terms of recognizing that. When you have this idea in your mind of what something can be, you sometimes don't see other options, you sometimes don't see those other opportunities, and it's important to give folks space, not just to say, go do this, or even how do we go do this, but to also say like, is there a better way to do this?

Matt: Is there another way to achieve the goals we're trying to achieve? Are the goals we're trying to achieve the right [00:34:00] goals? that if you open things up at that higher level, more interesting things are going to happen.



Rui: I really, really, really like this story. also the part of like, just taking yourself out of that room and the courage again. To remove yourself. to let a better outcome to emerge without you. That, that is a lot.

Matt: It's entirely possible that I just couldn't make band practice that night because of scheduling and I've rewritten this in my own history to be like an example of me doing something smart and brave, but regardless of what motivated it, the outcome was really good.

Rui: I see. Um, it sounds like you grew up in, New York, but now you're in London.

Rui: what motivated you to just move cross continent?

Matt: So I left 2017 and moved to Santa Fe, New Mexico. 

Matt: it was interesting because I left New York in part because I was having a lot of anxiety. My anxiety was really out of hand. And I thought that Being in New Mexico, like [00:35:00] being in the desert with the sunsets and the nature would calm me down.

Matt: And it did not, um, you know, there's that great expression, wherever you go, there you are. And there I was. So I was just anxious in the desert, rather than being anxious in the city. I remember once, um, I was cooking ravioli, because I did get much better at cooking, but I was making homemade ravioli and I got really frustrated and just started throwing the ravioli at the wall, and I was like, what is my life here?

Matt: I'm like throwing these ravioli against a wall in the middle of the desert. Um, so I think It was a good experiment. I don't think I would have left New York if I hadn't left it for something really different. that is one thing about New Yorkers is that we tend to see every other city as just a worse version of New York.

Matt: So I think I needed to get away from that to appreciate other places on their own terms. But, you know, I do think it gave me space to do work that I needed to do, but it certainly didn't do that work for me.

Rui: [00:36:00] Interesting. And I, I love the part where you, revealed that the anxiety basically just follow you wherever you go.

Matt: Yeah, I mean there's a book, um, by Jon Kabat Zinn, who's a great author about mindfulness called Wherever You Go, There You Are, it's worth reading, I found, because, especially when I was earlier in my career, I think I was in a pattern of burning out and running away, like I'd burn out, then I'd go on vacation, then I'd burn out, then I'd go on vacation, and trying to bring more balance to my life, like trying to just figure out What I want to do and what that looks like has been a really good challenge for me.

Rui: You know, the environment it's a huge factor in shaping how you feel, like, whether it's sunny today or not. But how you intrinsically feel about yourself, um, whether you can really at peace is. a huge thing that determines your mood all around.

Rui: Um,

Matt: the thing, right, is that those moments when you react poorly as a product manager are usually because of some deeply held [00:37:00] narrative about yourself that is being activated or challenged in the moment. if I'm at work and someone says something that makes me feel like I made a mistake and I hear like I'm a failure.

Matt: I'm stupid. I don't know what I'm doing. That's not what they're saying. That's the narrative that's been activated in my own psyche. So being able to understand that and say, Okay, that's not what they actually said. That's not what's happening here. I remember once when I was working, um, as a product manager at a company, I was like convinced that one of the engineers was mad at me.

Matt: Because I had kind of not handled, facilitating something super well. And I was convinced she was mad at me, and three days later I was like, Hey, can we talk about what happened the other day? And she was like, What are you talking about? I was like, Oh, you know that conversation? I didn't facilitate it really well.

Matt: She was like, I literally don't remember what you're talking about. I was like, Oh, I've spent three days being like, How do I bring up this horrible mistake I made that this person is clearly furious at me about? she was like, Yeah, you probably could have done better, but who cares?

Matt: Have more important things to worry about. Why are we talking about this? And I was [00:38:00] like, uh, Bye bye So that was a good reminder for me that you know, we all see things through our own particular lenses and I I think we all have a tendency to at times, Overestimate the impact of our own minor mistakes On other people.

Rui: for sure. And also I think there is an interesting part as you progress. you are able to take on a little bit more complicated problem. Um, when I was reading your second book, the draft, 

Rui: and 1 thing that you are trying to clarify is what exactly is a really a low versus high impact team. Um, and 1 point that was a little counter counterintuitive to me was, people in general, including me, would want to shrink away from metrics that you don't really have full control over project that will implicate coordinating, across many different teams that also probably have very [00:39:00] strong opinions.

Rui: And then it's very, very hard problem to really take on. And it's terrifying to take on those. but you pointed out, that's what potentially is required of you to help the business get to the next level, 

Matt: Yeah. I think that's another area where like therapy has helped me write product management books is that, that sense of control is so comforting and so addictive in a sense. And when I've worked with teams to set goals, one of the main issues that I've had is I'll say, well, this should be our goal.

Matt: And they go, well, we can't control that. And I'm like, of course you can't, if you could, you just would. But, Most goals that are worth achieving are outside of your immediate control. Otherwise every team would achieve their goals and every business would be infinity successful. That's just not how this works.

Matt: And I think the risk of not acknowledging the things out of your control. Is much greater than the risk of taking on things out of your control, you know when I was working with a company a while ago and they wrote somebody was like [00:40:00] well We can't achieve this without support from marketing and I was like good go talk to marketing Share this goal with them and explain that you need their help to achieve this and if they don't want to do it Escalate it if you need to and say we can't achieve this ambitious goal that matters to the business without these resources But in the absence of those ambitious goals, you're just wrangling for resources in a vacuum and I've worked with teams that are like, we can't do enough because we don't have enough engineers. I'm like, well, what could you do if you have more engineers? We don't know. Well, of course you're not going to get more engineers. Like, why would the business give you more, more resources if you can't describe how you are going to use those resources to deliver more value for the business? 

Matt: I think it comes down to the simple fact that any goal worth achieving Depends on customer and market behaviors that we cannot control Right, you can't go make a million people sign up for your product You can't decide if your competitors are going to launch something that's well funded that is going to eat away your market share Those those are [00:41:00] things outside of your control.

Matt: That's the reality of your situation um And part of what that means, which I tried not to belabor too much in the book, but is also true is that like sometimes businesses are going to shrink. Sometimes, you know, businesses are going to lay people off because things outside of their control happened, and they need to shift the way that they allocate and deploy resources.

Matt: That's, that's a reality of working for a business. And I think In most cases when both product managers and company leaders try to insulate folks from that reality It doesn't work because eventually that reality wins um And I cannot tell you how many product people i've worked with Who've worked for companies that have either gone out of business or laid people off where they had said If I understood the situation we were in I would have made really different decisions.

Rui: yeah, I guess what you were trying to say here is what brings the business value is sometimes the really tough challenge that you have to solve for [00:42:00] and this reminds me of, this monkey pedestal, brought up by Astro Teller, who work on special projects for Google, essentially it's about if you can have a monkey juggling Torches on a pedestal, you have a show business that you can sell tickets for.

Rui: now the most difficult part of putting together this show business isn't about building that pedestal. It's about getting that monkey to do exactly what you want it. To do, and you should tackle that monkey first instead of the pedestal. And if you feel like you cannot really get the monkey do exactly what you want to do, then you realize that maybe this is not feasible, at least at this point in time.

Rui: And you should just move on instead of illusion of you're making progress by trying to find a pedestal and build it up and building so many different pedestal But you just [00:43:00] don't have that monkey on the pedestal to do the show business,

Matt: Yep, I mean one of the analogies I use in the book is that it's like If you're building a car And the car doesn't run but you keep adding more and more decorations on the hood of the car and you're like oh we're gonna put like some diamonds on it we're gonna make it really pretty and then eventually you can't lift the hood of the car because there's so much crap on it and it's actually harder to get the car to run again so I mean you could take that further right and say that if you've made like a really ornate pedestal then like It might be harder, like the monkey might only know how to perform on that pedestal or might destroy the pedestal, who knows.

Matt: But if you put too much resources and too much time into optimizing and iterating on something, which is, which never stands to have the impact you need, it actually makes it harder to do the really impactful work.

Rui: let's say when you were taking a very ambitious goal and in general you really believe this is what's right for the business 

Rui: but you don't have the number to really, really [00:44:00] back it up. So how do we really convince other teams to join you in that goal and convince the company that, you know, other team could abandon whatever.

Rui: That's on their hand to join you. Um, a lot of times you don't really see that number until you actually do it.

Matt: So there's a story I told in the book of a team I was working with that was responsible for basically building the new version of an HR management platform that had, let's say, 50, 000 users on it. They were told, your job is to build the new version and get the old users onto it. And I was like, cool.

Matt: How many of the old users by when? And they were like, we can't answer that. Like, we don't know yet. I was like, well, then how do you decide what to do? Like, how can you decide? If you're building for 50, 000 users in a week, or for 50 users in a month, you're building really differently. Like, it's not just that those goals exist to, to communicate importance.

Matt: They also guide what types of trade offs you make and what kinds of decisions you make. So, I asked the team, [00:45:00] you know, what would you feel good about? You know, let's just make up a number. Like, what would you have to achieve by the end of the quarter to feel like the business got a return on this team?

Matt: And they were like, we don't know. And I was like, alright. Let me give you three orders of magnitude. We don't have to be precise, right? Like ten, a hundred or a thousand. And one of the engineers on the team said like, gosh, if we did a thousand, I would feel so awesome about the work we've done this quarter.

Matt: I was like, cool. Do we think we could get 10, 000? Everyone's like, no. I'm like, okay, cool. So it's a thousand. Like a thousand is our number. Let's go to this chief product officer and say we're committed to getting a thousand users on this platform by the end of the quarter. And what was really interesting to me was once we had the number in place, all the other decisions cascaded pretty naturally.

Matt: So then it was, all right, well, which thousand? What user profile are we going after? Are we going after people who signed up recently who might not be as entrenched in the old system? Are we going after people who are kind of our power users because we want to make sure that [00:46:00] we're getting them the best service as we build into the new?

Matt: But until we had a number, we couldn't actually unblock those decisions. Um, so I think part of the challenge is even if you're making up the number, Having a number is really important. This is really counterintuitive to me, as a person who's always thought of myself as like a qualitative person, but having that number, um, is really important.

Matt: Even if you are kind of reverse engineering it from vibes, like, if it was this many, that would mean that I'm kind of right about my instincts or whatever, then just commit to the number. Um, but if you don't have that specificity, I find it really, really hard to make decisions and also you run the risk that someone else has a number in mind that is completely different from your number.

Matt: And when you say, hey, we successfully launched this thing and got 100 users on boarded, they say, well, we thought we were trying to get 10, 000 users on boarded. What are you talking? Which is again, a very tenuous position to be in.

Rui: I like to measure things by numbers, [00:47:00] but a lot of times I find myself in a difficult position because I couldn't really make up the number. It's so hard for me to utter the number of something that I didn't do experiment over, right.

Rui: That I couldn't really tell you. With confidence that, hey, we're going to be able to achieve 10 million impact, So I would just say probably both qualitative driven and quantitative driven people have this issue, especially if you always want to anchor things in a little bit of reality. It's really hard to say, you know what?

Rui: I don't know, but I guess this is what we're gonna try to achieve.

Matt: Yeah, I mean if the business needs a 10 million dollar impact, then the business needs a 10 million dollar impact, right? I think that's part of why in the book I kind of start from understanding what the business needs via its business and funding models and then getting to how your team is going to contribute to that.

Matt: Because again, it really, you know, I've worked for venture backed companies where they're like, we don't want to be profitable. We want growth. We want to demonstrate traction in this market. Do not think about making money. [00:48:00] We do not want to make money right now. I've worked for publicly traded companies where We have a quarterly projection we've made that we have published to the market.

Matt: We need to hit this. I've worked with, you know, private companies that are like, we've promised investors that we're going to expand into this market. Doesn't really matter how much traction we get there, but we need to be able to come back to them at the end of the month and say, we're in this market. If you can understand that, then you can understand how your team is going to contribute to it.

Matt: but it's been interesting to work in situations, you know, work with nonprofits and other. Organizations where, you know, success doesn't always mean more money. there are a lot of different ways that businesses can define success. And again, the more specifically you understand that the better position you're in.

Rui: Yeah, for sure. We've chatted a really long time now. a wrapping question that I have is What is the stage that you're in right now? in your life and in career like what are you looking forward to? uh, or what are you trying to figure out 

Matt: Yeah, that's a great question. I mean, I think it's been a lot of [00:49:00] change in my life over the last five years. You know, I moved to London, I got divorced, my dad passed away. There's been a lot going on, a lot of change and a lot of upheaval. And I think the big question for me is like, what do I want to settle into? What do I want and how much do I want to settle into? 

Matt: Um, I just moved in with my girlfriend in London, which is wonderful. I wrote this book, which I'm really proud of. I'm excited to travel. I'm excited to be out there in the world and talking to people and doing this. One thing that I've been really enjoying, and you wouldn't know it from this t shirt I'm wearing, but I've gotten really into fashion. I have my whole closet of suits over here. I really like putting on a well tailored suit to give a talk. It kind of started as a little bit of introvert armor, but it's become part of my joy, 

Matt: Hold on. I'm gonna see if I can pull this

Matt: This like 90s Moschino. Um Which has this really cool zipper detail around the whole thing I [00:50:00] buy pretty much everything second hand this was something I saw online and took a risk on and it fits perfectly. So i'm really excited to wear this Um,

Rui: that's meant to be

Matt: yeah you know, I've been again working on this book at home a lot, so, dressing up and being in the world a little bit feels good.

Matt: I've also been doing, Reformer Pilates, like getting a little more comfortable in my body. I was in a meeting the other day and I was like, Oh, I sit up straighter now. so that was good. Just trying to, exist as a balance of, like, body and mind, travel and domesticity, self and community.

Matt: I think balance is the word that I'm trying to cultivate and figure out for this coming year.

Rui: This could be the last episode of Floating Questions, or it may not be. Either way, I hope you enjoyed flowing along with us today. [00:51:00] If you liked our journey, please consider subscribing. Thank you for listening, and may the questions always be with you.