Lenny's Podcast: Product | Career | Growth - Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor)

Starting point is 00:00:00 If you ever find yourself saying something like, that's not my job, that's probably a thing you should do. And you know, it probably isn't your job. And it probably is someone else's job. And you can spend your life getting frustrated at that or you can just get over and get the work done. And people who are willing to just get the work done will move faster, their products will be more successful. And they probably aren't carrying around all that anger and crappy emotion. Because as a PM, for better or for worse, and maybe this is a person. is not how we all want it to be, but you're oftentimes the emotional center of the team.

Starting point is 00:00:34 And it's your job to keep people motivated, keep people excited, keep them bought into the project. And you just have to keep that optimism going. And it's hard work. And part of it can be just like, you know what, let me take that on. I'll do this thing. I'll hop on this sales call. I'll implement this with the customer. You just have to do whatever it takes.

Starting point is 00:00:54 Today, my guest is Maggie Crowley. Maggie is currently vice president of product at Toast. Prior to this, she was VP and head of product at Charlie Health, senior director of product at Drift, director of product at Beth Spot, product manager at TripAdvisor. She's also got an MBA from Harvard Business School. She was also an Olympic speed skater, which is insane and incredibly cool. And in our conversation, we discuss the three most common threads

Starting point is 00:01:21 across the best product managers that she's worked with, hired, and managed, how to very tactically write out a product strategy to share with your team and manager, why being data-driven is a red flag for product thinking, why product content you find online can be dangerous, her best advice for how to break-ins product management, also the impact writing online has had on her career, and so much more, Maggie is amazing. I'm excited for you to learn from her like I did.

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Starting point is 00:03:53 head to composer.trade and use the code Lenny for an extra week, a free trial on your composer membership. That's composer.competre. Maggie, thank you so much for being here. Welcome to the podcast. Thanks for having me. I'm super excited. You put out so much content across podcasts, blogs, tweets. I'm sure there's other things I haven't even seen. And so what I've done is I've scoured all of your content as much as I could to find topics that we could dig into in our conversation today. And I thought it'd be fun to start with how to become a successful product manager and what it takes to be a successful product manager, especially long term in your career. You've worked with a bunch of PMs. You've hired a lot of PMs. You've managed a lot of PMs. And so I guess the question is just,

Starting point is 00:04:43 what are some common threads you've seen across the best product managers? Yeah, it's an interesting question. mostly because I've worked in, you know, startups, zero to one, scaling stage startups, enterprise, all that kind of stuff. And there's a lot of content out there, I think, on how those roles are different and how PMs are different across those different types of companies. But what I've seen is that there are some standard things that are the same across the role, no matter whether you're consumer, B2B, or startup, or a large company. And in particular, about what sets PMs apart from one another. and the things that I look for when I'm hiring or when I'm looking for promotion to promote people

Starting point is 00:05:26 or when PMs stand out, even when you're not looking, are three things. First, I think the best PMs are really good at breaking things down and simplifying things. So finding at any moment, like what is the really truly the only thing you need to do,

Starting point is 00:05:43 especially in a big company, there are 8 million priorities. There's 700 OKRs. There's 25,000 projects you could work on, and teams will get bogged down in that complexity. Similarly speaking, at a startup, you might think that it's easy to find the one thing to do, but at the same time, there's so many fires that are happening and so many things you could do in such a world of opportunity that even just picking one and sticking with it is really difficult. And so the best PMs not only can find the one thing to work on, but they can stay with that one thing long enough to actually finish it. I think that's a really interesting point because it sounds simple also, just this idea of simplifying.

Starting point is 00:06:19 But I think there's so much depth there, partly because within simplifying is prioritizing. And that's, you could almost boil down the job of the PMS. They're just prioritizing and telling people what is next. And so I think that's a really powerful point you're making. Prioritization is a tough word because there's so much wrapped up in that and what it means to prioritize. And, you know, I've worked for people who wanted to understand the formula for prioritization and why this thing and like, how can you prove that this is the right thing to work on and not. that thing and then, you know, a week goes by and then they're, they want to reevaluate the priority and they want to relitigate the priority. And so it's so much more than just a moment in

Starting point is 00:06:59 time deciding, but it's the ability to stay with it and to make sure that it continues to be the most important thing, that you finish it and actually see that it worked. And that you can get people to continue to stay excited and engage in that project because I think a lot of when we talk about product, it's like, oh, what should you build? What should you ship? But then you actually have to ship that and that can take a week, a month, three months, six months a year. And so as a PM, your job is to stay on that and be the person who's beating that drum over and over again. And the best PMs are the ones who can do that and have the resilience and that kind of like energy to stay with it. Energy. That's a really important part of that.

Starting point is 00:07:40 I'm going to ask you how you suggest people get better at these things. So either we can go into how you've found you get better at simplifying, or we go through all three and then we can come back. Let's just do all three really quick and then we can dig in. Sounds great. So yeah, first one, simplifying. I think the second one has to do at this point about sticking with something and it's following up on results.

Starting point is 00:08:02 So many people in the spec or the one page or something will say, okay, here's the metric that I care about. Here's what I want to move. Awesome. Maybe they'll even write a SQL query, get a dashboard going, figure out what the number is today. that gets you some extra points. But the really, really good PMs, remember to follow up.

Starting point is 00:08:20 Because especially when you're in management, a couple layers up in management, I'm not going to remember to follow up on that feature. But if a PM comes back to me and says, hey, remember we did that thing, here's what happened. I can't tell you how rare that is and how many times as a leader you might have to ask for that. And for the people you don't have to ask that of is one of the best things when I'm looking at PMs. And it's easy. Like, it's not hard to do that.

Starting point is 00:08:44 especially if you set up metric tracking or you know how to pull that information or you have somebody who can help you get that. It's pretty easy to do and it's really high, high value activity. And then the third thing, and I think maybe we'll talk about this later too, is that a phrase, actually we were talking about David Cancel before we started, carrying the water. And this was a big theme when I joined Drift. And this is about how you can't be a good PM if you're not willing to do the hard, boring, unglomerous work of, customer support, sales, marketing, writing, copy, project management. You have to do that stuff. It's your job. No one else is going to do it because at the end of the day, you're responsible for

Starting point is 00:09:24 outcomes and results. So you're the person that has to do that. And if you're willing to do that work, that's what's going to make your product successful, which is what makes you successful. It's such an interesting list because when you ask most people what you need to get better at to become a great product manager, it's always communication skills, collaboration skills, vision, strategy, and it feels like these are like input metrics to what it's normally what people think about. Those things to me, communication super important. Analytical ability, really, really important. The ability to look at a, especially if you're doing something and has a user experience component, the ability to look at that and understand if it's going to work and build up intuition around that,

Starting point is 00:10:05 also really important. Those are things that I would see as sort of basics of the role. These are the things that make you great, great at the role. And strategy to me, and hopefully we'll talk about strategy in a bit, it's one tiny slice. You do a strategy, but it's 5% of the work that you do. Yes, it's important because you want to get your strategy right and you need to pick the right products, but at the end of the day, the person who has a good strategy will not be as successful as the PM who ships more stuff, gets more reps, and has the ability to actually create impact. So to me, you could be great a strategy, but if you're not good at this stuff and your stuff isn't getting out the door, you're never going to be that great at the job. Yeah, and impact is the other one.

Starting point is 00:10:49 Everyone's always like, how do you, what makes a great PM? Oh, drive a lot of impact. But they never say how. Right, exactly. It's like, cool, let's do a strategy. Let's have impact. But then, and when I was starting off as a PM, I was hearing this advice and reading about it. And I was sitting there saying, awesome, I want to create impact. And I'm looking at my job thinking, how to what, now what? Like, yeah, impact. Let's do it. is it? How do I find it? Someone help me. I love it. Okay. So let's go back to these three and I'm curious just what you found helps you become better at these things and and also just like an example if you can share. So say with simplifying, how do you how does one build that muscle? This is a tough one

Starting point is 00:11:28 because some people, a broad generalization that I think comes up in things like when you're interviewing PMs for a job and you say things like are they a simplifier or are they complexifier? Do they make things complicated. And so some of it's a little bit of just who you are and how you think. But having said that, there's one tool that I use that I actually learned from my dad when I was in grade school, which is when you write something, for example, and a lot of what we do is PMS is written. When you write something, read it out loud. Literally just read the thing you wrote out loud. And half the time, you'll realize it's way too complicated. It doesn't make sense. Or what happens is when someone comes to me and they say, okay, I'm working on this thing,

Starting point is 00:12:08 you know, check it out. Can you read it? I read it. And then I put it down and I say, what are you trying to say? And 99% of the time they say, oh, users are really struggling with this problem. We found this in research and we think that the way to solve it is to do X. But that's not what the document says. And so my reaction is always, and if anyone who I work with is listening to this, they're going to laugh, is always, just say that. you know, just say that thing. The thing that you said to me in conversation is the thing you should write. There's no reason why your prose in a document has to be a certain way. We're not in school. Like, our goal is to get things done. So those are just some simple tricks that I've used to help

Starting point is 00:12:49 simplify what I'm, what I've already been working on. And as for how to boil things down and really find the most important thing to do, which is another part of simplification, I think the best thing you can do is just get as many reps in as you can, have people review your work and listen to them. There's a thing that happens, I think, with PMs where you join a company, and then all of a sudden it's like, my boss doesn't know what they, what they're doing, and, you know, highest paid person's opinion and, like, the founder wants to swoop in and mess everything up. But those people had an insight on the market that you're in that made the company worth founding, and they probably know more than you. And so you might want to listen to them. And so find people who

Starting point is 00:13:34 can review your work, listen to them and ask them to help you simplify. I'll share a couple other things that came to mind as you were talking, because this is like a very hard thing to teach and you kind of have to do it again and again. And honestly, I have this one manager who taught me to simplify in my writing and strategy docs, one pagers and things like that. And I think that actually had a big impact on my newsletter success is learning just to strip down as much as you can and kind of anything it isn't necessary. So there's a couple things that I'll share real quick. One is, there's this book I read called On Writing Well that is one of the most impactful books for writing for me. And the whole book is like, I don't know, 20 chapters and every chapter

Starting point is 00:14:12 is more things you should cut from your writing. And they show all these examples of like, here's a before and here's an after and all these words were cut and nothing changed. They're completely unnecessary. So I think that book can help. And partly it's just like what is not necessary. Like you think all these adjectives are important. Another thing I found really helpful is the rule of third, I guess, the rule of three. I'm just like always having three. Like try not to go beyond three when you're giving like strategy bets or priorities or things like that. Just like try to keep things under three.

Starting point is 00:14:44 Yeah, it's a very sort of business school ex-consultant point of view that I do agree with and share, which is there's always three things or fewer. Never more than three things. You have to have a nice round couple. And if you have a fourth, you've got to figure out how to squish it in there because it just doesn't look right if there's four. Yeah. Even though I've been guilty of more than three, but try hard to avoid it. Yeah, like you're using Notion and you have your three bullets expanding and there's sub-bullets,

Starting point is 00:15:12 but at least you have that top line. That's right. The other thing is I think there's just like a focus you need to get better and good at. Just like people often want to lump together a bunch of ideas and then every time you do that, it just deletes everything. So I think there's just a lot of power and like pick the thing. Pick the thing that's going to have the most impact and cut other stuff that may have some impact, but is much less important.

Starting point is 00:15:30 I think again, simplification as something in prioritization, which is sort of the same thing, gets tossed around a lot as a thing you have to get good at. But it's really challenging. Like getting to the one thing you should do is extremely difficult. And being able and having the gumption to say no to all those other things is really hard because there's probably at any given time 10 things you should do. But you can't do 10 things. You'll never be successful if you do that in a number of things. And so you have to pick one. And so it's both figuring out how to get confident in your decision and then be having the willingness, and maybe I should have added this to my what makes great PM's list, the willingness to make the bet and be responsible for it. And that's why I think separates the PM role from a lot of other roles and why it's such

Starting point is 00:16:19 a challenging job when done right is because you have to be willing to take responsibility. And it's your job to pick the thing. And it's your job to be accountable to your team for picking the thing. so you better get it right. Ownership. Such an important part of just being a PM. Again, coming back to this interview, I just did with an ex-Amazon guy, that's one of their principles at Amazon is just leaders,

Starting point is 00:16:42 basically ownership, feeling like you have ownership of what you're working on. I agree, but to me at least the word ownership doesn't have the same, like, oh, shit, feeling as you're making a bet. Like, you make a bet. That means you know that there's a chance of the thing you're working on is not going to work out, and you still have to be the one to like do the thing, jump off the ledge, like drop in on the ski run. So ownership to me never signaled that like risk that I think comes with being a PM.

Starting point is 00:17:10 Good point. On the Simplify concept, it reminds me at Airbnb. One of the core values at Airbnb for time was Simplify, is this idea that we should always try to be simplifying. And then it turned out the founders realized we're not actually great at this and it's unfair for us to say this is a value for not doing it. So they actually cut it as a core value because their feeling was we shouldn't have aspirational values. We should reflect who we actually are.

Starting point is 00:17:36 And they actually cut two different values to be more clear. Even though they still want to simplify, they're just like, we're not actually good at this. So why are we pretending like we are? I think maybe I'm good at it on paper, but there's been many times where I've been in situations where things are not simple. And you just have to keep fighting for it. Someone's trying to think about, okay, I want to get to become better as a PM. I'm going to try to start simplifying. What are examples of simplifying?

Starting point is 00:18:01 Like, is it reduce your email length? Is it one page or focus? Like, what are these buckets of things? And then also if there's an example of something you've simplified that comes to mind. On what to simplify and more specifics, I would say anything can be simplified and shortened. Maybe another way to say shorten it. Definitely emails.

Starting point is 00:18:22 Like, I read them sometimes. Don't love them. make them short. The Minto principle is something that I would recommend everyone do, which is like put the headline, the full conclusion first, and then you're supporting argument second. I have a newsletter post about that exact concept that people that will link in the show notes. That gives you exactly how you use the Minto Pyramid principle.

Starting point is 00:18:43 Yes. Everyone should do that. A lot of new PMs fall into the trap of thinking that they should like have some sort of buildup. Don't do that. Just tell me whatever the thing is. Everyone will thank you. Doing things like that. Things like you said,

Starting point is 00:18:55 limiting your strategy docs, your conclusions, your next steps to three things, maximum. I would generally say a rule of thumb would be pretty much every doc you write. You can delete the first two paragraphs that you've written. You don't need them. My dad, again, to go back to my dad, he, when I would write in the sounds cruel, but I promise it wasn't, when I would write a paper for school, he would just like, and this is bet we didn't really have computers, whatever, he would just take away the first page and he'd be like just start just start here everything he would go

Starting point is 00:19:27 everything on the first page is crapola don't use it and he wouldn't even read it which would drive me crazy he would just like oh it's crap I don't care about that so I would do that and then just get other people find there's probably somebody around you that's good and find people to edit your work and to look at it

Starting point is 00:19:45 I have a little Slack workspace that has three people in it me and two other women who are product leaders. And we oftentimes send each other our work still. And we say, like, hey, I'm struggling with this. Like, can you read it? Help me make it simpler. Can you help me fix this up? And we do that for each other. So find a peer, you know, maybe who's in a non-competitive space. You can do that for you. I mean, I still use those people to help me. That is extremely cool. Can you talk more about this group that you have? Yeah. I don't know if it's a group. It's like three friends. Shout out Alexa and Daphne.

Starting point is 00:20:20 Yeah, I mean, the three of us all worked together. when we were at Drift, we've stayed in touch. And I've just found that in order to be good at your job continuously, you need people who can help give you feedback in that. And the more senior you get, the harder that is. And so having people who can give you another point of view, who maybe you can vent to if it's not appropriate as a leader, who can give you other experiences that they're going through has been incredibly valuable.

Starting point is 00:20:45 And so we just have a little group chat that is focused on product. That is so cool. Is there like a tip you could share for someone that wants to create something like this? Is it important for you to have worked with them before? Is Slack a good way to communicate? Anything there that's just like, oh, yeah, here's a cool tip. Slack just work for us because that's where we are during the day. And I think having easy access to it was important.

Starting point is 00:21:06 You could probably use WhatsApp or a literal group text. There are small community. There's one I worked in healthcare for, you know, a year and a bit. And there's a Slack community that somebody organized for heads of products and healthcare startups that is similar to those really, really powerful and a really great space to be in. And so you just have to kind of suss out where these things are. You work with amazing people and there's people around you who are going to become your friends. And so keep an eye out for them and keep in touch with them when you leave a job because you never know when they

Starting point is 00:21:35 might become your little slack workspace. Oh, I love it. Okay. I'm glad we talked on that. Okay. Back on track, the second bucket you described as following up on results. How do you, is it just do that? Is there anything more you can add there? I put reminders in my calendar. I mean, yeah, it's just do that. But like, if you're launching a product, usually, you know, you release something and you have that initial push of a couple of weeks where you're finding bugs and maybe you're pulling metrics and everyone remembers it, then I would remember two weeks after that, a month after that, six months after that, put a reminder in your calendar to check your dashboard or check the metrics or check whatever it is that you were doing. A,

Starting point is 00:22:14 you won't forget and then share them with whoever. might care about it. And it's as simple as that. And is the reason this is one of the three things you think are most consistent across great PMs that it helps your manager see you like, wow, Maggie is so on top of everything? Or is it more that you learn from that experience and drive more impact? Or is it both?

Starting point is 00:22:35 It's definitely both. I don't, I'm not going to pretend like if you're just great at your job quietly that you're going to get what you want, right? You're not just if you're toiling in the background, doing a great job, getting results. If you have a great manager, maybe you'll be successful. Great managers are few and far between. And I'm of the opinion that I never wanted to rely on someone else to get what I want it. And so I would always make sure to share that.

Starting point is 00:23:04 Always make sure to share my progress because I didn't want to leave it up to chance that someone would notice. So I would just doing it for both reasons. And that's one of those things that, like, you know, people want to pretend that everything's perfect and we're all great and we're always going to get what we want and always going to get that promotion. But you have to work for it. I love that point. It reminds me one of the, what I find one of the most important traits of a great product managers, they create this aura that they've got this. They put something on their plate and they're not going to drop it. That the threads, threads are not going to be forgotten. And this connects to me there. They feel like Maggie's going to. tell me what happened with this experiment. I could not have to, I don't have to think about it as a manager. Yeah. That's a really good point. And then the, this, you mentioned this a little bit ago, the side benefit is that you learn more. You know, you, you'll go back and learn why something happened or why it didn't happen. And the more that you follow up on what you've been doing

Starting point is 00:24:02 and the more you learn, the better you get every time you ship something. To me, like the other answer of what makes a great PM is you shipped a lot of stuff. Like, the more you ship, the more you ship, the more you learn. And that's why it can take years to build up expertise, because you just have to ship a lot of stuff. There's a lot of people that are always frustrated. They're not getting promoted quickly enough as a PM. They're not moving up the ladder. Like, oh my God, I've been a PM for two years. I'm not a senior PM yet. Can you speak more to just that thought and just how long it takes to get actually good? I guess I'll share briefly in my experience. It's taking me four years to like actually know what the hell I was doing as a PM. And then things started to

Starting point is 00:24:38 really take off. What's your experience? I would say similarly, took a lot of years to feel confident that I knew what I was doing. My first PM job was a product management rotation job at TripAdvisor. I had no PM background. I was after business school. And I left that those two years thinking like, yeah, I've worked on four different teams over the two years. I've shipped all this stuff. Like I'm good. Went to a startup was free. There was another product person there. They left. Then I was the only product person at the startup. And I realized really quickly. I had no idea what I was doing. Like I had no one to learn from. I had only had two years of experience and I was not ready for that job. I didn't feel confident in the decisions

Starting point is 00:25:17 I was making. That's why I joined Drift is because that team had all these really incredible product thinkers on it. And they were shipping all sorts of stuff. They had all this momentum. And I thought, okay, that's where I'm going to go to learn. And so then, you know, two more years. So that's five years until I really felt like I knew what I was doing. And that's because it takes a long time to ship stuff. And so to people who want to progress, you can progress by job hopping. You can progress by, you know, going in and out of startups. But to me, staying at that's when I was a drip, I was there for almost four years, I got to see two or three cycles of the same product. And that, I learned more from that than I did out of the, you know, year or so I spent doing

Starting point is 00:26:02 other things each at a time because you got to see the consequences of, you know, the consequences of your decisions. And that's rare and people, you know, myself included. Of course you want to get promoted. Of course you want to, you know, move up. You know, I'm ambitious. Lots of people are ambitious. But for better, for worse, spending the time is really helpful. And I think allowed me to move faster later because I had just spent the time grinding it out for a while in order to be better later. So is that advice you often give of go deep into a company or product versus just bounce and try a bunch of different companies, or it depends? It depends. There are lots of really good reasons to bounce. I've done it. Many people have done it, but I was surprised at how much

Starting point is 00:26:49 I value that experience of having stuck around for a while and how much I learned from it was something I hadn't expected going into it, especially because you don't hear that point of view as much, or as I wasn't hearing that point of view as much when I was thinking about the sort of arc of my career, but I'm glad that I did it. And then, you know, of course, people always want to get promoted, always ask that question. And my answer is always create impact. And that can take time. Yeah. At my first job, I was there for nine years. And then I started a company for a year and a half. And then we sold it to Airbnb. And then I was at Airbnb for seven years. So I'm very much on that train of just like, not that I intended for that to happen. But I definitely went deep. And

Starting point is 00:27:31 I think there's pros and cons, but there's so many pros to that. So many reasons. Okay, let's talk about the last part, which is the third point you made, which is carrying the water, I think is how you described it. Yeah. This one, there's no tips and tricks. It's just do the work. If you ever find yourself saying something like, that's not my job, that's probably a thing you should do. And, you know, it probably isn't your job.

Starting point is 00:27:58 And it probably is someone else's job. And you can spend your life getting frustrated at that or you can just get over and get the work done. And people who are willing to just get the work done will move faster, their products will be more successful. And they probably aren't carrying around all that anger and crappy emotion. Because we touched on this earlier as a PM for better or for worse, and maybe this is not how we all want it to be. But you're oftentimes the emotional center of the team. And it's your job to keep people motivated, keep people excited. keep people excited, keep them bought into the project.

Starting point is 00:28:32 And you just have to keep that optimism going. And it's hard work. Like it's really hard work to stay positive and to keep people amped for that thing. And part of it can be just like, you know what, let me take that on, you know, let me grab that, whatever. I'll do this thing. I'll hop on this sales call.

Starting point is 00:28:51 I'll implement this with the customer. You just have to do whatever it takes. It reminds me of one of your lessons that you share, from in one of your podcast episodes, it was one of your PM lessons of 2021. And the lesson was when in doubt, it's your job as a PM, which I think relates very much to what you just shared. Can you speak to that? It might actually make sense to put this in the context of the other roles that are part of the team. So as an engineer, your job is to write the code to really reduce this down and build the thing and make it work to spec. As a designer,

Starting point is 00:29:25 maybe your job is to design the thing, design the solution, design user experience. obviously there's a lot more complexity in that role. Design, you're amazing, engineering, you're amazing. TLDA, or caveat, whatever. But as a PM, you don't have that thing, right? It's not like, oh, my job is just to write the one-pageer. Like, that's not true. Your job isn't just to pick the problem.

Starting point is 00:29:46 Your job is to deliver a business result. And so you're uniquely positioned to have to fill in all the gaps because no one else is incentivized to do that. Like, you could, as an engineer, you can finish your work. and hand it off and say, I did it. And you don't, the good ones care, but you don't have to care, right? As a PM, like, you're not going to do your job unless that problem gets solved for the customer or the user at the end of the day. And so your job is to make sure everything happens for that product.

Starting point is 00:30:17 It reminds me of another interview you did where you talked about how a lot of the PM job sucks. It's not as glamorous as people often think. and most of the job is these really boring, annoying things. I guess is there anything you want to add there? A lot of people, see Lova want to get into PM. Are like, oh, I'm going to run the show. It's going to be so great. I'm going to be a product manager and tell people what to do.

Starting point is 00:30:39 But that's not how it is. It's just one of those things that like people. And when I joined product, it was just sort of becoming a cool job. It wasn't like the hot job on campus when I was in business school. That was more like private equity venture capital. and now there's a sense of cachet around it. But again, it comes back to that earlier point, which is you do get to do cool stuff.

Starting point is 00:31:02 You get to decide what gets built. Like, that's cool. You have a lot of ownership like we talked about. You could see it as you have a lot of power. But at the same time, you're responsible. And so with that comes this responsibility to get it right to make the right bets, ship the right products, get them out the door.

Starting point is 00:31:19 And that's, there's a lot of bullshit work you have to do. You know, again, project management is one everyone hates on. Qua is a really good one. You should QA your products. Like, that's great. If you have a QA team, you should cuea them. You should know how they work. You should implement with your customers. You should be able to sell them. You should be able to, you know, find users. All that stuff is stuff that you should be able to do. And none of it is above you. If someone is listening and they're not a PM and they are not convinced to not get into product manager, they still want to become a PM, what is your best advice for someone that is trying to

Starting point is 00:31:52 get into product management of how to actually break into product management? I thought about this one a lot, and I consulted the Slack workspace team because it's been a long time since I tried to get into product. And so I didn't know what was going on these days because it's hard. And I hadn't, I didn't, I don't know if things have changed. You know, I went to business school and that's how I got in. There was a program that took MBA students. I think there are some entry level programs out there at big tech companies. if you can get them, I think they're really hard to get because they're very few and far between.

Starting point is 00:32:26 And so the most common two paths that I've seen are people who switch laterally within a company. Again, challenging but can be done. Are people who join startups. So when I was at my last startup, I did hire someone who was coming out of business school who hadn't been into product into a PM role. And like, I can't say I wouldn't do it because it was awesome and she was amazing. But it takes a lot of work. The reason why people don't do it is because as a manager, it takes a lot of work.

Starting point is 00:32:52 because there's so much that these people need to learn. And what we ended up doing is she and I spent four months working together in a we work in person to help her onboard really quickly into the role, which was so rewarding. And I loved every second of it. And I wish I could do that again and again and again. But to get that, she basically just hounded me. Christina, if you're listening, you emailed me a lot. We talked a lot.

Starting point is 00:33:17 And we waited until the time was right. And then you finally convinced me to do it. So I don't know. I don't know if there's a reliable, if there's a reliable path that I can say, like, this is what my advice would be, other than, you know, try a startup, network, see what you can do.

Starting point is 00:33:33 And you've made it at this point elsewhere, which I think is an additional key piece. As once you have a PM title on your resume, everything gets easier. Because as a hiring manager, I'm just like, I look at a resume, like, oh, they've never been in PM. I'm not, I'm not, like, I'm not, this isn't the role.

Starting point is 00:33:47 It's like rarely that does someone want someone that's never been in PM? Yeah, and I tell people, I do unsurprisingly talk to lots of people who either are in product or want to be in product. And that's one of the things I always tell them, because they're, you know, if they're deciding between roles and they have an opportunity to do something. And my advice is always, if you can get someone to stamp you with the product manager role, take it. Because to your point, it's what we screen on. It's for better for it. It's just like you just have to, you have to get that first job. And then once you get that first job, it all gets easier because you can get in and then you can talk about your experience.

Starting point is 00:34:21 because then the second question I have is, what have you shipped? Right? So it's like, have you been at PM before? What have you shipped? And it's fascinating how quickly people can't answer that question. And the people who can are always several steps ahead of the people. Let's shift topics and talk about product strategy. Many people are told, you need to get better about product strategy.

Starting point is 00:34:45 You're not great at strategy. A lot of people are also just confused. What is strategy? How do we get better at strategy? How do we describe a strategy? And you have a really great explanation and overview of how to think about this stuff. So I'd love to hear your take on just how do you actually write out and describe a strategy? Sure.

Starting point is 00:35:05 Yeah. Another thing that happens, and I'll give the outline, but another thing I hear, especially as you get further in your career, and unfortunately, if you're maybe an underrepresented person in tech, is that you need to be more strategic. And so that's feedback that almost always happens, especially if you're a woman in product and tech who's knocking at the door of a leadership role, you've probably gotten that feedback. And so I made it my mission to figure out like what the heck is this thing? How do I do it? How can I do it in a way that is demonstrable so that I'm never getting that feedback that's like, oh, she's not strategic?

Starting point is 00:35:40 And so what I did was something that I kind of did in the background because I had an engineer who I worked. with who really wanted to understand why we were doing what we were doing. And he was not satisfied with sort of a surface level answer. And he was just pushing and pushing and pushing. And so what I did was I just wrote out a Google Doc. And I started with like, okay, and not fancy. These are just bullets. What is the mission? Like what is the point of the company? What are our goals? Maybe we have some sort of high level framing of what we're working on. And then I had this big section that was just like the landscape. And in that section, I put in, you know, what's going on with our business, what's happening with our product, what's our point of view on the market, who are our competitors,

Starting point is 00:36:25 you know, a SWAT analysis, key risks that we might be facing, just dump that all on paper. Then what are the current quarters, business goals, or whatever, however you do planning, like, what are the current things that your company is working on? Then I put in, all right, that's sort of the context that we're operating in. Then I wanted to understand where are So what is an honest accounting of the current state of your product, you know, the business overall and then the specific area that you're working in? What works? What doesn't work? What are your customers saying? Bottoms up feedback users, customers, teams. What are your support tickets? Get that all out on paper. And then really importantly, where are your technical hurdles? Like what are the big pieces of tech debt? You know, what are your engineering and technical teams always harping on that they want to invest? And then, what are, what are the big pieces of tech debt? You know, what are, what are your engineering and technical teams always harping on that they want to invest? invest in, you know, are there some like big things coming down the pipe that you need to think about? Just get everything on paper. And then usually in the process of writing all that down, you'll start to see, okay, I kind of get where we are. I kind of get what the challenge is. And then you write a

Starting point is 00:37:33 section that's like, what's the opportunity? From all of that, what's going to bubble up as the top one or two opportunities for your team? Where do you want to play? Where can you win? you know, where's the unique, based on like your unique competitive advantage, where do you think you all should be and why? And then based on that opportunity, what are the challenges, right? So like, what's going to be the hardest about taking advantage of that? What has to be another way to frame it is, you know, what has to be true about the world for that to work? That's a one that's been helpful. And then what would you do? Like, take a swing at writing down your solution. you would need to build, how might it work, anything that you have. This is where I would say

Starting point is 00:38:16 three bullets, maybe, what you might want to do. And then a plan. Like, if no one else had an opinion, how would you go about it? How would you sequence it? What would you do? How might you get the team to work on it? What would your team have to look like? How much would it cost to do it? All that. You can start to layer in all that kind of stuff. And then I just share the doc. Like, share it with everybody. There's no, there should not be any secret. and you should be able to walk all the way from your company's mission down to the individual priority on your team and see the logic chain and why you got there. And if anyone doesn't agree with it, they can call out where their disagreement lands in that landscape. But at least then

Starting point is 00:38:57 you've put everything on paper, you understand how you got to where you're going, and then you can have an argument about the different pieces and points of data and feedback that you're getting, but at least people understand how you got where you got. And then it doesn't become like, I don't agree with you. It becomes I don't agree with this point. This is such a cool way of doing it. By the way, is there a template that we can point people to that has this sort of? There's not.

Starting point is 00:39:23 It's just, I've only ever done it in like a loose Google Doc. And then, you know, it just grows and changes. I can maybe try to write up those bullets. It's just like, I just make headers. And then I just start dumping content in it. That's all people need. If you end up creating that before this comes out, We'll throw it in the show notes.

Starting point is 00:39:40 And if not, people can just bother you on Twitter and ask Maggie, where is that template that we talk? Yeah. I'm happy to, like, write it on a piece of paper and take a photo of it and send it around. Just make it really grainy and like an artifact. We found Maggie's template. This is awesome. So I've never heard of a version of this with so much depth into the landscape. And I think that's so smart because so much of conflict and disagreement comes from, you just don't have the same information.

Starting point is 00:40:06 or the manager, exec or whatever, is like, doesn't think you have the information. So if you just lean into, here's everything that I know and here's what's happening. And if you disagree with this,

Starting point is 00:40:14 call tell me, and then it'll change the plan. Right. Yeah. And part of it's also that typically speaking, when you're doing a strategy, you're doing it at a higher level.

Starting point is 00:40:26 So I don't think like every product needs a strategy. Like every feature doesn't need a strategy, for example. Like you don't need to do this if you're like, working on a tiny slice of a product and you have user feedback like don't over complicate it, just do the stuff that makes sense. But, you know, especially as I've gotten more senior in my career, the questions are bigger and the impact is broader and the timelines

Starting point is 00:40:50 are longer. And honestly, it was also because I wanted to get it right. Like I didn't want to make a bet on something and put a bunch of resources against a problem and get it wrong. And so this was also like homework that I wanted to do for myself to know that I was going to do the right thing. for some reason I'm always paranoid that other people have more information or like doing it better than I'm doing it. And so I was like, okay, I have to write it all down and then make sure I got it right and share it with everyone and make sure that they agreed with me so that I didn't screw this thing up. And it just was such a useful exercise that I kept doing it. And of course, people don't read it. People only read a tiny section.

Starting point is 00:41:26 And like, you'll run to the same problems. You run in with everything else. But at least I knew that I had done the work and if people cared to engage with it, it was there. So on those lines, I was going to actually ask. How long do you find this should be depending either on the time scale? Say you're doing a quarterly strategy or a year. How many pages should this doc be any, any guide? It's long.

Starting point is 00:41:46 Okay. It gets real long. Like what is long? I've had some, because the actual content, I end up writing a summary to go back to the Minto principle. I end up like doing the whole thing, then putting a summary at the top. So that there's one within the first above the fold, if you will, you can kind of the whole point and the suggestion on what I think we should do or what the strategy should be should be summarizable in that section. But like it can go 20 pages just because if you

Starting point is 00:42:16 really want to get deep in a competitor or there's interesting market dynamics, interesting technological changes that are happening. Like I sometimes I'm screenshoting other companies marketing websites and like dumping that in there and that might be some interesting content. So there's all like it doesn't have to just be words or can be all kinds of different things. you might want to put in there. And you made the point that it's not like you expect people to read this whole thing. There's the summary that gives them a conclusion. And in theory, if they want to really dig into it, they can. But I guess how do you find that balance of writing everything you know and making it so long that no one's ever going to read it to like, here's, it's actually

Starting point is 00:42:54 going to be useful to someone and plus here's a summary? It comes back to the reason why I write the document in the first place. And that's for me. So it's my home. work to do my job effectively, I just make sure to share it. And I find that my, especially my engineering and design counterparts, if you're working in a true triad, will almost always engage really deeply on the dock because they're pretty much also on the line and they want to make sure that when they sign their teams up to do whatever it is, that they believe in the thing that you're working on. And so I find that those people will engage pretty deeply. Sometimes you'll have more junior folks on the team that'll just be interested and like they'll get really into it too

Starting point is 00:43:36 and then there's you know some people that'll skim the upfront part and either say yeah it looks great or you're dumb I hate this and like okay sure there's always those people so it never really matter to me that people read the whole thing it was more I knew I had to do it to be confident in my own decisions and then it can facilitate a conversation so like it didn't really matter this episode is brought to you by Epo Epo is a next generation A-B testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams. Companies like Twitch, Muro, ClickUp, and Draft Kings rely on Epo to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the

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Starting point is 00:44:58 Epo powers experimentation across every use case, including product, growth, growth, machine learning, monetization, and email marketing. Check out Epo at getepo.com slash lenny and 10x your experiment velocity. That's get ePPO.com slash Lenny. Is there an example of a strategy you were thinking about recently or that you worked on in the past just to give people something concrete of like here's what Maggie thinks of as a question she's going to develop a strategy around? Yeah, I think, I mean, so obviously this is where in product content.

Starting point is 00:45:32 think it's really challenging because I obviously can't, I can't really talk about the stuff I'm currently working on. Just tell us all of the secrets and nobody will know. The Toast's PR department would be really unhappy with me. It's questions like, you know, if you're a director of product somewhere, right? Maybe you're running a section of a business and it's annual planning. We're in Q4.

Starting point is 00:45:54 What are you going to do next year? How do you answer that question? How do you back up your choices for that? You use a doc like this. maybe you are realizing that the product that you're working on doesn't really matter. It's not really making an impact. You're kind of treading water. I would use this as a tool to figure out, okay, well, what else could you do?

Starting point is 00:46:17 So, yeah, quarterly planning, annual planning, if you feel like your team needs to make a pivot, or if you think that there's a really interesting new opportunity that your business or your team should go after is another time I might use something like this. Awesome. This reminds me a little bit of, I just, I keep mentioning this chat with, Bill Carr that I had who was an early Amazon exec and how the narrative approach at Amazon, one of the benefits of that and the reasons they go there is partly for you to realize this is a bad idea before anyone even needs to give you feedback. And that's why they force you to write six pages in depth about your idea. And then it goes in these concentric circles through

Starting point is 00:46:52 the company. And ideas like, here's, okay, and this is just not a good idea. Here's all the reasons why. So I think there's a lot of similarities there. Yeah, there are many, many times. when if you combine this artifact and process with the point about simplification, where through that process, you just start cutting so many things. Because then what happens is, let's say you've gone through this exercise and you're like, okay, I know exactly what my three things are that I want to work on. Then you, there's a moment where you take the strategy and then you look at your roadmap. And they're never the same.

Starting point is 00:47:29 And the roadmap is just bloated with all of this random stuff that like, oh, well, we have to do that because of this or we have to do that because of that. This thing we're still working on. This is like six months to late. So we're still going to do the thing. And then all of a sudden, you've got 90% of your resources committed to things that don't track against your strategy. And it's a really interesting moment as a leader, especially to sit there and go, well, what do we do? Like, what do you when you have that problem? And especially if you're a PM, you probably don't have the agency to say, scrap the entire roadmap and work.

Starting point is 00:47:59 kind of my new strategy, but at least it allows you to think about critically about whether you should be doing what you're doing and allows you to evaluate whether those things are still the most important things to work on. I'm going to summarize the template real quick, and then I'm going to have another question kind of along the line. So if you're trying to create your own little template, you start with the mission, the business, and then I imagine you also show the mission of your team, because oftentimes it's a little more specific if you're working on it like a product team strategy.

Starting point is 00:48:25 Then there's a landscape of what's happening. So you include competitive, like SWAT analysis of competition, risks, product state, business state, things like that. And then you share the current goals of what you're trying to achieve as a team slash business. And there's an honest accounting of what's happening in the product and technical hurdles and things like that that'll keep you from moving, I guess, achieving some of these goals. And then you share, here's the opportunity I see how we win and how we actually achieve this opportunity. where we place bets and things like that, or we could place bets, then challenges of doing this, what needs to be true for this to be possible. And then you actually, then you finally get to here's what I think we should do, essentially the solution, ideally three bullet points.

Starting point is 00:49:13 And then the plan. And I imagine the plan is step one, gets line off from exec, step two, resource the team. Step three. Start on this design research sprint. Pretty much. All right, amazing. Somebody will create this template if you don't end up doing it. There's another. I hope somebody does. Okay, that'd be awesome.

Starting point is 00:49:35 If they do, I will tweet it and we will put it in the show notes. So many promises already from this podcast. Along the same lines, you also have a one-pager template and process that I think people find really useful. So how about we chat about that one briefly? And then I'm going to go in a whole different direction. Okay. Yeah, the one-pager, I don't think I have much. much to say about this that has not been said by many people many times,

Starting point is 00:50:00 but whether it's a spec, a PRD, a one-pageer, I don't even know what else people call it, it's the document that you use to define the thing that you're doing as a product team. And that means like product design engineering, like your little squad. And what I think is really useful about this process is that it's the PM's artifact. So, you know, designers produce designs, engineers write code, you know, what do PMS do. A lot of people might say nothing. In theory, we write at least this document, right? And it can be a pain.

Starting point is 00:50:41 I've seen lots of ways where it hasn't been done very well. But when I think it's done really well and when it's really effective is it's a tool that allows the PM to start with why. And if you structure it correctly, the most important section, in my opinion, in the document, in is the first part, which is like, what is the background and context? What is the problem? Why does it matter? And why does it matter now? And if you get those things right, the rest gets really easy, but it gives you a chance as a PM to center the team around the problem, you know, why that problem exists, whether it's created by, you know, your own product or it's something the user is experiencing and why that problem is worth solving. That's a part that I think people

Starting point is 00:51:24 sometimes forget to think about and like why it's worth solving right now versus all the other problems you could be solving. And then it can become the home base of the decisions that you make along the way. So I think it's best when you have those sections and then also best when you you write down, okay, on this day, we made this decision or we decided not to do this or we decided only to solve this part of the problem, not this part of the problem, keeping a running list of that and the link off to all the different artifacts and research and things is helpful for a routine. So just to summarize, what would be the headings again, just if someone's taken notes and wants to create their little template? I don't think these templates have to be very complicated. It's like background and context, the problem.

Starting point is 00:52:03 I would literally write why this problem matters and why this problem matters now. Like, don't make it complicated. Just answer those questions. And if you can do that. And then, again, it's only really helpful if then you bring that document before you go any further to your team. and you use it to have a conversation, and you get the smart people around you to take shots at it. I should have mentioned this earlier with the strategy. The first person I go to was typically speaking, my engineering counterpart, and I say, like, shred this. Like, go through it, rip it apart, vomit comments on it, like, tear this down because that's how it gets better. And as a PM, you can't be, like, precious about your work. You have need people to, like, poke holes in it.

Starting point is 00:52:48 The Why This Matters Now point is so interesting. I don't often, hear that. And I think it's such an important part of specs and plans and strategies, because there's so many things you can do. And there are certain things that are perishable that you can only do now, that if you don't do now, you miss a big opportunity. And so I think that's a really interesting element that most people don't include. And it reminds me of, I think I've done enough podcast episodes now where I'm just connecting all these things as people are talking. It's like the John Nash thing happening, where Kari, the founder of Linear, talked about this concept of side quests as a founder because he's so good at staying focused.

Starting point is 00:53:24 And I was just like, how do you stay focused and just get stuff done? You have so many people coming out. He's just like, there's the main quest and there's the side quests. And side quest I don't need to do right now. There's the main quest, which is build a really successful business. And I feel like this is a good example of that in action. Yeah, I love his take on quality and taste too. Yeah, what a jam.

Starting point is 00:53:44 Yeah, big fan of that. But yeah, I mean, it's really hard to stay disciplined. It's hard to stay focused. And to your point, there's a million things you could do at any given time, especially if you work at a bigger company. And so the why now is an important question to answer because if not, somebody is going to ask you. So you may as well think about it.

Starting point is 00:54:01 Yeah, it's interesting. Why now comes up a lot in investing in startups, but rarely in product building. And it feels like it should. Although I will say in the research I've done, why now ends up not being that important for startups being successful or not. So I think there's two sides of that coin. Anyway, I'm going to move on to a different topic. and this might become a new thing that we do,

Starting point is 00:54:21 and I'm going to call it Contrarian Corner. I asked you if you have contrarian opinions about things before we started recording this episode, and you had some really good ones. So there's a couple topics I'm going to chat about, and we'll see if this becomes a recurring theme, and you're laughing and nodding your head. What are you thinking as I say this?

Starting point is 00:54:39 I'm thinking about when I had a podcast, you would do a show on a topic, and we would click the end recording button, and then every single guest would be like, I had no idea what I was doing. I made it all up. It was waterfall. It was just like that,

Starting point is 00:54:53 none of that matters. Like, I didn't know what I, like, it was just people would say the wildest stuff. And I would sit there as a PM and just think like, what? Like,

Starting point is 00:55:01 we just talked about this framework. We just talked about this thing. And like, that's how you're supposed to do it. And then they would get off the, get off the official part and just say, yeah, it's wild.

Starting point is 00:55:09 Like, nothing goes the way you wanted to go. Like, we're all just kind of making it up as we go. And so I hope that you get more of those, in this part of the show. I'm very sensitive to that point right now because someone just tweeted about how they're just finding that

Starting point is 00:55:23 many of my newsletter posts about how companies write product are like the ideal version of what they do. And I rarely, or they rarely share, here's all the challenges we're having, which I think there's truth of that, but I also get into a lot of failures on this podcast. Actually, I think the podcast is a lot more of just like,

Starting point is 00:55:40 here's things that go wrong versus the newsletter. So I'm just like, shit, I need to do more of that. So I love that you mention that. and let's yeah let's see what we can get into. But I guess maybe before we get there, is there an example of something that didn't go right just along the lines of some sort of failure slash mistake? I might be foreshadowing,

Starting point is 00:56:00 but a question I ask in every product interview is, what's the worst product you ever shipped? And that's because I don't think you're a good PM if you haven't shipped something that's really shitty. Like you just haven't had enough reps, you haven't done enough time. And it's not only that you've done it, but that you can admit it and you know which one it is. Like that's so important.

Starting point is 00:56:21 And I remember, this is so dumb. I'm still so mad about this that we did this. It was, I won't name which team, which company I'm not going to call that out. But we decided we needed to do a rewrite red flag number one of a existing product. And, you know, engineer who I'd work with many times. We had a really good relationship. And this person was like, yeah, it's going to take six months. No problem.

Starting point is 00:56:47 Core part of the product, been around for forever. Like one of those things that the code is still the code written by the founders kind of thing. It didn't take six months. It took two and a half years. It still wasn't done. It almost never, like, it went on for so much longer than it should have. It took us forever to get to feature parody. It was the worst project. Like so many people rotated in and out of it. Everyone thought it was dumb. Like sunk cost fallacy. just the worst. And it's because, A, we got arrogant and we thought we could do it.

Starting point is 00:57:20 B, we skipped discovery. We didn't really write a one-pager. We just went for it. We didn't do enough technical and design research into what the requirements would actually have to be. And there you have it. And it did not work out. Where was it a huge success in the end?

Starting point is 00:57:36 It changed the trajectory of the business. Absolutely not. But you know what? I didn't get fired. So, like, it's fine. I feel like I've gone through those experiences and then like three, four years later, it's like another, maybe this rewrite and redesign may work because just we haven't updated this thing in a long time. Just don't do it. Don't rewrite. If anyone ever tells you to do a rewrite, don't do it. A side-by-side rewrite, nope. Yeah, I've never had a, like what I run into is once you get too far down a redesign slash rewrite, everything is building in that new world. And then you launch it and the experiment's negative. And then it's just like, oh, we just got to launch it. We're going to claw back. We're going to figure out how to get back to new.

Starting point is 00:58:12 someday. Yeah. Yeah. Yeah. Don't do that. Good times. Okay, well, maybe we'll start a failure corner. That could be a new segment. We'll even have a little sound and theme music. But this time we have contrarian corner. And you have a couple contrarian opinions about a couple topics. The first is product management. What is something that you believe about product management that maybe other people are less convinced by? The one I like to have in this area is, that people who are really excited about being data-driven, to me, that is oftentimes a red flag for their product thinking. Especially if it's, you know, an executive who's saying things like, oh, we're so data-driven. We make all our decisions, you know, with our dashboards.

Starting point is 00:59:02 To me, that says that the team is over-emphasizing quantitative data at the expensive qualitative data, and they're not using good judgment. They probably don't do a lot of direct user research. They don't really understand the humans who are using the thing, what they need, what they care about, and they're managing via a dashboard. And maybe if they got really, really good at picking metrics, it would be fine.

Starting point is 00:59:29 And oftentimes maybe it is fine. Maybe you have a high-volume business that's really easy to run experiments on, and that works for you. But most PMs, most jobs, most products, you're going to be better off talking to 10 users and you'll get more and better insights out of why things are happening than you would with any dashboard. So the takeaway there is just like be careful when someone is saying they're so they're super data driven. Our team is

Starting point is 00:59:57 super data driven or company's super data driven. Yeah. And maybe it's true, right? And that's great. Like I'm not saying that you don't need data. You you absolutely do need to instrument your products and understand if it's working at scale. But you can't forget that you need to know why. Like, it won't tell you why anything is happening. If you don't understand why it's happening, I don't think you can come up with good insights about what you should do next.

Starting point is 01:00:19 One quick story on this, I remember really early on my career, Adam Medros, who was the Vee Fioront at your trip advisor. We were in a room. We just had this meeting called Product Review that was amazing when I first joined. And someone was like justifying this project. And he just, and I hope he is a,

Starting point is 01:00:36 okay, I'm saying this, because this is my memory of this moment. He was just like, this is an obviously better thing. Like, just do it. Like, stop, stop, stop it. Like, stop doing all the stuff that you're doing. Like, stop with these numbers, like, whatever it was that they were doing. Like, if it's obviously better, if it's logically better, use your good judgment to do that thing and, like, let's move on.

Starting point is 01:00:52 And I've always thought about that, but, like, you can just do the obviously better thing. Yeah, I love that. I pull that card sometimes. But I think you almost have to do it that way. Just like, okay, everyone. This one's just like obviously a good idea. Let's just do it. Enough research.

Starting point is 01:01:10 Okay. Another topic that you have some interesting opinions about is product content, very close to our hearts, both my heart and your heart. Do share. Really, if you're going to make good content, like you have to sanitize and framework guys, the thing that you're working on. And then slowly, I think, for a lot of people who are reading it

Starting point is 01:01:35 and looking at it, they, like, their thinking starts to become, well, look how well I did this framework. Look how well I implemented this thing. And they lose touch with the point, which is, like, creating impact. And so all of this content makes it really noisy and then makes people think that, like, oh, if I just do these things, that I'll get what I want. And now I'll just check off my list. And then I checked it off. And then I should get my promotion at the end of the day. But it's like, the best PMs have built up so many different frameworks. and they can apply them in different ways, and then sometimes they throw them out.

Starting point is 01:02:08 And they say nothing I have in my toolkit makes sense for this moment, but I know what to do because I have intuition and I have data and I've talked to users or whatever. And so content sometimes can get in the way of the impact because you're trying to apply it and you think that the point is the framework or the point is the one-pageer

Starting point is 01:02:24 or whatever it is that you're doing when it's not. And then if you're a leader, and maybe if you've had the good and ill-fortune of having published content, someone comes to you and says, well, you said in that one podcast episode that you don't believe in Roadmap, so why are you asking me for a roadmap?

Starting point is 01:02:39 And then you're the asshole who's sitting there being like, well, it's like a little more complicated than that. And that was a fun take that I had. But like, I actually need to understand what we're doing because we're planning and like I need to figure out what my budget is, blah, blah, blah. That's so funny that I didn't think about like you as a leader having put stuff out that people put back at you.

Starting point is 01:02:56 And I think your point about one for you, for people to consume content online about how to do product management. You have to like really distill it. And to your point, yeah, it often loses the nuance. Because if you had all the new ones, no one's going to even read it because it's so complicated and long. Right. And then the other point of there's also just like, it has to be interesting.

Starting point is 01:03:17 So if it's another just like, here's how to roadmap really successfully. And it's like what everyone's already done. No one's going to read it. So you always have to kind of have a new take. And with that, it comes like, it's not actually always true. I just kind of wanted people to react to this idea. Yeah. I mean, it's helpful. I think all of the, there's some people who create, I mean, I, there's many things at my last role, we would, you're, we all had your newsletter and we listened to the show and then people would bring, I can't, I can't, I can't have found a clip, but I can't remember. There were a couple of moments where we, we would listen to a piece of it or find an article and say like, oh, like this could help or what if we did it that way. I think there was a newsletter article about Figma and they had some templates. They're like product review template for, for,

Starting point is 01:04:03 fig jam. Love that one. Use that one all the time. Amazing. And so yeah, I mean, this stuff's really useful. It's just like you have to be smart about when you apply it. And then if you're a leader and there's all this content available, you have to be, you have to know why you're not following the rules. Right. Like if they're just like, hey, look at this newsletter post lighting right. We should be doing it this way. Versus like, I think people assume these are the one way to do it or innately will work at your company. And I really like your important, which, you know, maybe counter to what I do, but I think it's an important nuance that I feel like I should add to every

Starting point is 01:04:36 newsletters. This isn't necessarily going to work at your company. Like sometimes there's, the culture is different and this won't fit or this isn't a complete version. As much as I try to give people, here's everything you need to do this thing. Well, there's always a little bit missing. With, and it can be a little, I think if you don't have that context, it can be a little demoralizing because it's like, well, how, like, how am I ever going to do that thing that they, that they get to do at this magical company? But again, if you, you've, it as more like, hear all the tools that you can add to your toolkit and you pull them out when you're in a situation for which they can be useful. That's how I think about it versus like

Starting point is 01:05:12 this is the one way to do it. Like you said, you know, the only way you can write a one page or the only way you can run an experiment, it's more like you can do it in many different ways. Yeah, and I find myself, I'm not actually, I rarely tell people here's the way to do it. Usually what I tried to describe is here's how the best companies do it as much as I can get into and leave it to the reader to decide is this going to be a fit for me? Should I try to implement it? But still, I think there's an implication. This is the way to do research.

Starting point is 01:05:39 Here's the way to do roadmaping. Here's the way to prioritize. But I think it's interesting that you also yourself create a lot of content. And you actually found a lot of value from being a, let's not call you a content creator because I don't want, I don't like being labeled as a creator myself. Someone wants called me a product influencer and died like a little bit. That's how I feel. I'd love to hear just the impact you've seen from spending time, creating podcasts and blog posts and tweeting about really great stuff because a lot of people are thinking about investing in this stuff.

Starting point is 01:06:10 Yeah, it's probably the best thing I've ever done for my career. And I'm so grateful for the people who, whose idea was, who supported me, you know, especially adrift when that, when that became such a part of what we were doing at that time. And it's been helpful for a couple of reasons. One is just networking and access. Like, I probably wouldn't be here today if I hadn't done that. And if, you know, friend of a friend, had read the thing, you know, it's like it just creates so many more connections. And so access to people and networking is one of the first benefits. Also, you know, building a personal brand is really helpful if you want, one of the things that I always wanted to do with my career is try to make it so that I'm always employable. You know, I didn't, I just didn't want to like, you know, I'm an 08 grad not to put my age out there. And it was a hard time. And so, So I've always had this in the back of my mind. Like you want to be able to have a solid career.

Starting point is 01:07:13 And so I thought that like investing in my personal brand would be a way to help help me, you know, get access to roles. It helps in recruiting as well when I'm trying to hire people because a lot of my job now is like bringing people in. And because I've been vocal about how I like to work and who I am, a lot of people self-select. And they will send me a note and say, I want to work with you or I want to work on a team like that.

Starting point is 01:07:35 And that's huge because if my job is to hire people, then that's great. And people can get a sense of who I am. you know, without needing to be on the phone with me. My favorite benefit outside of those things has been that I've, it's helped me learn more from the work I've done than I otherwise would have been able to. Because in order to make content, you have to think through what you did. You have to summarize it, process it, make it interesting for people. And then, you know, especially if it's in a podcast medium, talk to somebody about it.

Starting point is 01:08:06 And the process of doing that means that you're paying attention to what you're learning along the way. And so often we don't do that because we're busy working. We have our lives. Things are happening. And that to me is I think what's made me a better product person faster is because I spent the time to think about what I was doing in a way that I wouldn't know if I wasn't, if I didn't have to write something now. Something that comes across in your content that you've somehow figured out is to avoid it being cringy and very thirsty for followers. and I think when a lot of people here build a personal brand, it's like, ah, I don't want to. It's like, yeah.

Starting point is 01:08:42 I know. It's like makes me ill even saying that. Yeah. Like, I never, I never thought of it or wanted to think of it that way. And I'm just curious what advice you'd give to people that want to go down this route without feeling. I guess one is just feeling like they're being cringy into avoiding content people will be like, oh my God, I can't believe. Yeah. Yeah.

Starting point is 01:09:02 Yeah. Yeah. Clickbait. Yeah. tweet thread situation. You know, I think the step one is going to be cringe. Like your first 10, 20,

Starting point is 01:09:12 however many posts are going to be bad. I would imagine if you went back and listened to your first episode, you would be cringing just because you've learned so much since then, right? Like, it's natural. Although randomly, the second, the first episode ever is the most popular

Starting point is 01:09:26 episode, yes, with Shreos, which I could see why it was so popular. Yeah, so you started, like, went really hot with your first guest. That's right. So yeah, first get over the fact that it's going to be cringe, it's going to be cringe. Like anything, you just have to get started. And it'll fade away eventually and you don't have to think about it.

Starting point is 01:09:46 To be, this is such gross advice, but like you have to be authentic. It has to be real. And I think what came through in the show that I did was like, those were my real questions that I was really working on. So we joked about how we would turn off the recording and then we would get the real story. but I would turn the recording off, then I would say, okay, we talked about this thing. Here's what's actually happening in my job today. What would you do? And so those were real questions that I had, real processes that I was working on and real

Starting point is 01:10:15 advice that I needed at that time. And I think that's why it was valuable. It's because I was actively a P.N. And the way that I'm still actively in product, that was always something that I wanted because it meant that the content had to be relevant for me and wasn't just for, you know, likes and shares. I think there's some two really important points there that stood out to me. One is your stuff's going to be terrible if you don't actually have any background or experience in the thing. So you're just like pretending. It's like you're acting like someone that

Starting point is 01:10:45 knows about this thing, but you don't actually. And so I think that's an incredibly important part of this is don't try to become an online creator person if you haven't done the thing because people will see that you don't know what you're really talking about. And you'll run out of stuff and he'll be like, okay, well, I did it for two months and I have nothing more to say. Right. Right. And then the other piece is there's a guest who shared this quote that has stuck with me from Einstein, which is something like seek not to be successful, but of value. And I find that that's a really good framing for sharing stuff. It's just like share things that are interesting to you and useful and come at it from like, this is useful, not from I'm trying to build a following. Because

Starting point is 01:11:28 people can tell if that's the... Yeah, people can absolutely tell. And the other thing is there's a little bit of like too cool for school mixed in here. And there are definitely people who will tell you your content as cringe or make fun of you or whatever because that's what they want to do. And maybe I'm not even going to get into psychology of that,

Starting point is 01:11:52 but like people will do that. And I've always been of the mind that the really interesting people out there are people who are unashamedly interested in stuff and who are like, yeah, I'm nerding out about this and I'm sharing it because I'm interested in it. And for better, for worse, like, I love working in products. I love the job. Even all the gross stuff you have to do. It's super interesting. You meet really cool people. You get to ship stuff. You get to see the stuff get used by people and solve problems. It's a really cool job. And I've always been interested in how to do it better. And it doesn't matter to me that some people might think that's cringe because like, that's cool.

Starting point is 01:12:22 But this is what I do all day long. So like I'd like to get better at it. I think that's such such a big part of it. I didn't even mention that just like, it needs to feel like really authentic and clearly for you is just like, there's just stuff I want to share it because it's really interesting to me. Yeah. The way I actually started writing was exactly the two reasons. You just shared. One is I wanted to learn the thing and so writing helped me figure things out. And then two is I just thought it was interesting and I found it useful and I just assume other people might find it useful. So I did also learn and I wonder if you found this too, is that

Starting point is 01:12:57 you think the things you know are not going to be that interesting or useful to people because they're so basic for you. But people are finding the most basic stuff so interesting because there's always more to learn about how to roadmap, how to prioritize, how to hire, how to talk to have difficult conversations, performance review. All of that is absolutely true. And I think one of the first pieces of content that I was really happy with was like I was working with somebody and they were making a PowerPoint present your slides or whatever. And I just wrote out in my notebook like, okay, here's how

Starting point is 01:13:31 I do that. Like, right? I start with an outline on paper and then I draw little boxes for the slides and I write out the headline of the slides. And then once I have a tight outline and I have the literal text that will go across the top of each of those things, then I sketch out how I want the slides to go. And then I go into Google Docs and I actually make the slide. And it was like some silly little thing and this person

Starting point is 01:13:54 sat there and said, holy shit, you just totally changed the way I did this. And I, this took me 75% less time than it would have taken me otherwise. And I was like, I made you this dumb drawing. Like, why is this a big deal? And yeah, that's when I realized that like the stuff that's easy for you might be the stuff that is most interesting because it's something that maybe you're really good at that you don't realize.

Starting point is 01:14:13 I think people need to really internalize that point. Like, if there's something that you're doing that you consistently find useful and works, often that is going to be really useful for someone to hear. So that could be a good place to start. Yep. Maggie, we've gone through everything that I was hoping to get through and more, which is awesome. Before we get to our very exciting lightning around, is there anything else that you want to share, touch on, think might be useful to leave folks with? I hope that people, my hope is always that people listen to stuff like this and realize that it's messier than you think you can fail a lot and still be successful and that they should have fun.

Starting point is 01:14:51 I think that also gets missed in a lot of the product content is like have fun, enjoy it. People are weird. People do weird stuff. And you build stuff for people, which it makes it all very entertaining. So I've always found a lot of joy in the job. And to your point of carrying the water as a PM where you're kind of doing all the things, it's like you can create that fun. You can make the team you're on fun and change the culture, create the culture. I find that so underappreciated for a PM. Absolutely. Okay. Well, with that, we reached our very exciting lightning round. Are you ready? I'm ready. Maggie, what are two or three books that you've recommended most to other people? First, most common one is probably the presentation secrets of Steve Jobs.

Starting point is 01:15:31 It's a little tiny one. Really great way to improve your speaking skills and your presentation skills and to get distracted executives to agree with the point you're making. So that's one. Thinking in Betts by Annie Duke is the second one. I'm coming back to the point about being able to make bets. I think that one's a really interesting one. And then bonus third one, this is more like a desk reference that I now have on my desk. The Scaling People book by Claire Hughes-Johnson, I really enjoyed the way that one is working,

Starting point is 01:16:06 and it just sits on my desk, and I reference it every once in a while, especially as manager. I have it both under my laptop right where I'm sitting and then also way behind there. And it's one of the most popular episodes I've done with Claire, so if folks haven't listened to that one, I highly recommend. She's incredible. Great choice. What is a favorite recent movie or TV show? You've really enjoyed. Okay. So my husband is in the industry, as we say, here in L.A. And so we watch a lot of good and bad shows and TV. But I think my favorite one that I've watched recently was Slow Horses. Gary Oldman is incredible. Highly recommend. Wow. I haven't heard that one yet. Good tip. What is a favorite interview question you really like to ask, which I think you already

Starting point is 01:16:49 gave away, but let's touch on it again. Yeah, it is what is the worst product that you've ever shipped. I think the best answers are ones, and I don't even care if someone listens to this, and then I do this in an interview. People immediately laugh a little bit. They remember the horrible thing they did, and then they share that horrible thing with you. And it tells me, you know, you have some humor. You're humble and you can point out when you've made a mistake, right?

Starting point is 01:17:16 you've done enough to be able to confidently say, like, of course, I've made a mistake because none of us are perfect. And you know how to spot those mistakes and you can learn from them. And I've always found that those conversations are the most interesting. What is a favorite product you've recently discovered that you really like? One, because I've seen you on Twitter, you're a future fit guy. Yeah, I am. Is that correct? I use it three times a week.

Starting point is 01:17:38 Yes. Yes. I was also a future fit person. I think it's great. It's a great product. I'm now on ladder fit. I've heard of that. And personally, I love not being, I don't have to talk to the coach every day.

Starting point is 01:17:52 I don't need the accountability. So that's not a thing that I needed as an ex-athlete. So for me, that didn't serve me. And I like the anonymity of it. And it comes with a totally unhinged group chat for your whole team. It's fantastic. I'm really enjoying it. Sweet.

Starting point is 01:18:08 So that's one, more of a funny one. And the second one, not to like get real niche, but I think good products are products that are focused. They do one thing incredibly well, and they're not, to your point about side quests, there's no side quests. I'm a new mom. There's this app called Pumplog. I have never seen an execute so well on one problem. There's not a single thing where I think, oh, I wish it did this. It does it.

Starting point is 01:18:35 It's like I paid $14 for it. I've never paid for an app like that in my life. Okay. I'm downloading it right after we finish. Do you have a favorite life motto that you either repeat yourself often to share with folks find useful in just kind of living life? I'm sure there's models I could say that would be aspirational mottos. But the real one is like if it's worth doing, it's worth doing well. And, you know, from, again, from being in sports to, you know, going to school to being in product.

Starting point is 01:19:07 In my opinion, if you're going to do something, do it to the best of your ability. because that's what you do with your day. You spend so much time working. You may as well be good at it or trying to get good at it. And that's always how I've lived my life. I so love that message. I always think about that. Final question.

Starting point is 01:19:25 You are an Olympic speed skater, which I don't think people would know necessarily that's insane. My question is, is there something about speed skating that would surprise people? That would be like, what? Ooh, that is one I've never been asked before. The whole experience, I've obviously learned a ton from it. And I think what might surprise people about being a small sport athlete is that you have to think in four or eight year chunks.

Starting point is 01:19:54 And so it's one of those things where you grind for so long in like a dark corner and then, you know, you get a chance to come, you know, sort of get the light to shine on you. And you learn how to love the process. and especially for speed skating, I was a long track speed skater. It's a 400 meter rink. You just are always turning left and going in a circle. Like there's not a lot going on. It's just you and your thoughts. And you just really, really learn how to get good at perfecting something over and over again.

Starting point is 01:20:26 And you learn how to grind, you learn how to focus. And I think it's also cool. You get to go super fast. But yeah, I don't know if that would surprise people about speed skating. But I think just about being a small sport elite athlete, It's really about like years and years and years of toiling and silence to get maybe, maybe one shot at something great. So much of what you just said would apply 100% to product management. And I love that.

Starting point is 01:20:51 Maggie, you are awesome. Two final questions. Where can folks find you online if they want to reach out and maybe ask you any follow-up questions? And then two, how can listeners be useful to you? You can find me on Twitter for sure. I LinkedIn, but just being of cringe, like I just can't get into the LinkedIn post. LinkedIn's gotten better. I'd give it a shot. It's like actually pretty interesting now. Yeah. I'm thinking about it. I go back to work in a couple of weeks and thinking about LinkedIn.

Starting point is 01:21:21 But yeah, Twitter for sure, LinkedIn for sure. And I've always tried to be helpful to other people. So I don't have an answer for how people can be helpful to me. My goal is really to share what I've been doing, the rooms that I get to be in, the access to the content and the people and the learning that I've had. So hopefully I can find ways. to keep sharing that. Maybe check out toast and use toast when they're at restaurants. Oh, yes, plug, toast, come work with us. We're the best. I get to work with John Cutler. It's phenomenal. Legendary previous guest. Are there roles you're hiring for just for folks that are listening and just like, hey, maybe I should go do that. There are always roles that are open. I don't know what the most open roles are right now, but yeah, check it out. It's a great place. We'll link to the careers page. Maggie, thank you again so much for being here. Thank you, honey. It was awesome. Bye, everyone. Thank you so much for listening.

Starting point is 01:22:11 If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lenniespodcast.com. See you in the next episode.

Lenny's Podcast: Product | Career | Growth - Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor)

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