Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor)

23:53You 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 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 if you have to ship a lot of stuff. Like 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.

24:26I'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 on my experience. It took me four years to like actually know what the hell I was doing as a PM. And then things started to really take off. What's your experience? I would say similarly it 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. Had no PM background. I was after a business school. And I left that those two years thinking like, yeah, I've worked on four different teams over the two years.

25:00I'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 my decisions 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.

25:29And 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 Drift. With 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 other things each at a time. Because you got to see the consequences of your decisions.

26:08And that's rare. And people, you know, myself included. Of course, you want to be up promoted. Of course, you want to, you know, move up. You know, I'm ambitious. Lots of people are ambitious. But for better or 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 budget different companies or depends? It depends. There are lots of really good reasons to bounce. I've done it.

26:45Many people have done it. But I was surprised at how much I value that experience, have 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, I, people always want to get promoted, always ask that question. And my, my answer is always create impact. And that can take time. Yeah. I am my first job. I was there for nine years.

27:20And then I started the company for a year and a half. And then we sold to Airbnb. And then I was at Airbnb for seven years. So I'm very much on that train of just like, but not that I intended for that to happen. But I definitely went deep. And I think there's just 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, 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 seeing something like, that's not my job.

27:54That'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 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 them bought into the project.

28:32And you just have to like keep that optimism going. And it's hard work. Like it's really hard work to stay positive and to keep people amp 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 the sales call. 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 shared 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.

29:10Can 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, 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 your amazing engineering. You're amazing. TL, they are caveat whatever. But as a PM, you don't have that thing. Like it's not like, oh, my job is just to write the one page. Like that's not true.

29:44Your job isn't just to pick the problem. 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. It reminds me of another interview you did where you talked about how a lot of the PM job sucks.

30:23It's not as glamorous as people often think. And the most of the job is these really worrying, annoying things. I guess is there anything you want to add there of just like, you know, a lot of people see love 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. But that's not how it is. It's just one of those things that like, people and when I joined products, 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.

30:56And now there's a sense of caches around it. But again, it comes back to that earlier point, which is, you do get to do cool stuff. You get to decide what gets built. Like, that's cool. You have a lot of ownership. Like we talked about, you can 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. And that's so there's a lot of bullshit work you have to do. You know, again, project management is one of everyone hates on. QA is a really good one.

31:27You should QA your products. Like, that's great. If you have a QA team, you should QA 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 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 get into product management or how to actually break into product management? I thought about this one a lot.

31:57And I consulted the work, 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 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. Big tech companies, if you can get them, I think they're really hard to get because they're very human far between. And so the most common two paths that I've seen are people who switch laterally within a company.

32:31Again, challenging, but can be done. Or people who join startups. So now 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. 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 on board really quickly into the role.

33:03Which is 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. And we waited till the time was right. And then you finally convinced me to do it. I don't know. I don't know if there's a reliable path that I can say. Like, this is what my advice would be other than, you know, try and start up network, see what you can do. And you've made up this point elsewhere, which I think is an additional key piece is once you have a PM title on your resume, everything gets easier.

33:40Because as a hiring manager, I'm just like, I look at a resume like, oh, they've never been a PM. I'm not. I'm not. This isn't the role. It's like, rarely that to someone wants someone that's never been a 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.

34:13It's for better force. 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. Because then the second question I have is what if you should? Right? So it's like, have you been a PM before? What if 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 at product strategy. You're not great at strategy.

34:46A lot of people are also just confused. What is what is strategy? How do I 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. Yeah. And another thing that happens, and I'll give that 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.

35:28And so I made it my mission to figure out what the heck is this thing. What 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. 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.

36:05These are just both. 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 competitors? 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's working on?

36:40Then I put in, all right, that's sort of the context that we're operating. Then I want 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? What are your engineering and technical teams always harping on that they want to invest in?

37:17Are there some 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 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? Where's the unique based on your unique competitive advantage? Where do you think you all should be and why? And then based on that opportunity, what are the challenges?

37:54What's going to be the hardest about taking advantage of that? What has to be another way to frame it is? 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, and what you would need to build, how might it work? Anything that you have, this is where I would say, 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?

38:33How much would it cost to do it? All that, you can start to layer and all that kind of stuff. And then I share the doc, like share it with everybody. 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 they're where they're disagreement lands, like in that landscape. But at least then 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.

39:09But 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. It's just, I've only ever done it in like a loose school doc. And then it just grows and changes. I can maybe try to write up those bullets. I just make headers and then I just start to think constantly. Yeah, it's all people need. If you end up creating that before this comes out, we'll throw it in the show notes.

39:40And if not, people can just bother you on Twitter and ask, Maggie, where is that template that we talked about? Yeah, I'm happy to like write it on a piece of paper, take a photo of it and send it around. There we go. Just make it really greeny and like an artifact. We found Maggie's template. This is awesome. So I've never used for her to have 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. Or the manager, exactly whatever, it's like, doesn't think you have the information.

40:10So if you just lean into it, here's everything that I know. And here's what's happening. And if you disagree with this, cool, tell me in the middle change of 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. 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 -complicated. 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.

40:49And the timelines 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 like 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.

41:19And 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. And like you run to the same problems, you run them with everything else. But at least I knew that I had done the work and 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 guy? It's long. Okay. It gets real long. Like what is long? I've had some because the the actual content I end up writing a summary to go back to the Minto principle.

41:57I end up like doing a whole thing then putting a summary at the top so that the one within the first above the fold, if you will, you can kind of get the the whole the point. And the suggestion on what I think we should do or what the strategy should be is should be a summarizable in that section. But like a keynote 20 pages just because if you really want to get deep into competitor or there's interesting market dynamics, interesting technological changes that are happening. And like I sometimes I'm screenshotting other companies marketing websites and like dumping that in there and that might be some interesting content.

42:32So there's all like it doesn't have to just be words or it can be all kinds of different things that you might want to put in there. And you've 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 this actually going to be useful to someone and plus zero to summary. It comes back to the reason why I write the document in the first place and that's for me.

43:04So it's my homework 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 doc 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. And then there's you know some people that'll skim the upfront part and either say, yeah, they'll look greater.

43:43You're done. I hate this. And like, picture. There's always those people. So it never really mattered 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 I could facilitate a conversation so it didn't really matter. This episode is brought to you by Epo. Epo is a next generation AB testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams. Companies like Twitch, Miro, ClickUp and DraftKings rely on Epo to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features.

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44:58Epo powers experimentation across every use case, including product, growth, machine learning, monetization, and email marketing. Check out Epo at getepo .com slash Lenny and 10X your experiment velocity. That's getepio .com slash Lenny. Is there an example of a strategy you were thinking about recently or that you worked on the past just to give people something concreative like here's what Maggie thinks of as a question she's going to develop a strategy around? Yeah, I think, I mean, it's obviously this is where a product content gets really challenging because I obviously can't, can't really talk about this stuff.

45:35I'm currently working on this. Tell us all of the secrets. Yeah, I know. But the toast care department would be really unhappy with me. It's questions like, you know, if you're a director of products somewhere, right? Maybe you're running a section of a business and it's annual planning, we're in Q4. What are you going to do next year? How do you answer that question? How do you put, 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.

46:12I would use this as a tool to figure out what else could you do. 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's an early Amazon exec and how the narrative approach in 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.

46:46And that's why they force you to write six pages in depth about your idea. And then it goes in these concentric circles through the company and the idea is like, here's, okay, 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, 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 to this exercise and you're like, okay, I know exactly what my three things are that I want to work on.

47:22Then you, there's a moment where you take this strategy and then you look at your roadmap. And they're never the same. 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 away. It's 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?

47:53Like, what do you do 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 on 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 of the business. And then I imagine you also share the mission of your team because oftentimes it's a little more specific if you're working on it like a product team strategy.

48:25Then 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 account, 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, things like that, or we could place bets.

49:02Then 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. And then the plan. And I imagine the plan is step one gets line off from exec. Step two, research 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. Yeah. There's another. I hope somebody does. Okay, that'd be awesome. If they do, I will tweet it and we will put it in the show notes.

49:39So 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. You're the one -pager. I don't think I have much to say about this that is not been said by many people many times. But whether it's a spec, a PRD, a one -pager, 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, you're a little squad.

50:17And what I think is really useful about this process is that it's the PM's artifact. So, you know, design, 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. 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, is the first part, which is like, what is the background in context?

51:00What 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 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.

51:34So, I think it's best when you have those sections. And then also best when 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 has helpful for a team. So just to summarize what would be the headings again, just if someone's taken notes in one secret, they're a little template? I don't think these templates have to be really complicated. It's like background in context. The problem.

52:03I would literally write why this problem matters and why this problem matters now. Like, don't make it complicated. Just put 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.

52:38Like 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 to need people to like poke holes in it. 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's certain things that are perishable that you can only do now. That if you don't do now, you miss the 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.

53:12Where I'm just connecting all these things as people are talking. John Nash, they happening where um, Kari, the founder of linear talked about this concept of side quests as a founder. He's so good at staying focused. And I was just like, how do you stay focused and just get stuff done. We have so many people coming. I use 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 up really successful business. And I feel like this is a good example of that in action. Yeah, I love his take on on quality and taste too.

53:43What a jump. Big, yeah, big thing to 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 can do at any given time, especially if you work at a bigger company. And so the why now is is an important question to answer. Because if not, somebody's going to ask you. So you may as well think about it. Yeah, it's interesting why now comes up a lot in investing and 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.

54:13So I think there's a 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. 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 of 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? 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.

54:46And 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. 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? We just talked about this framework. We just talked about this thing. And that's how you're supposed to do it. And then they would get off the official part and just say, yeah, it's wild. 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 takes in this part of the show.

55:18I'm very sensitive to that point right now because someone just tweeted about how they're just finding that 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 to 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, here's things that go wrong. Where's these letters? So I'm just like, shit, I need to do more of that. So I love that you mentioned that. And let's, yeah, let's see what we can get into.

55:50But I guess maybe before I 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 may be foreshadowing, but a question I ask in every product interview is what's the worst product you ever shipped? And that's because I, 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 it enough time. Like, 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. And I remember one was so dumb.

56:25I can't, 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 wanted, 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. Core part of the product, been around forever. Like one of those things that the code is still, is still the code written by the founders kind of thing. It didn't take six months. It took two and a half years.

56:58It 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 future parity. 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 we got arrogant and we thought we could do it. 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 then now we're out. Where was it a huge success in the end?

57:37Changed 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 or four years later, it's like another. Maybe this rewrite and redesign may work. Because we have an 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. Aside by side, rewrite. Nope. Yeah, I've never had a... Like what I ran into is once you get too far down a redesigned slash rewrite, everything that's building in that new world and then you launch an experience negative.

58:07And then it's just like, oh, we just got a launch. We're going to claw back or get a figure out how to get back in neutral someday. Yeah. Yeah. Don't do it. Good times. Okay. Well, maybe we'll start a failure corner. That could be a new segment. You may have a little sound and theme music. But this time we have a contrarian corner. And you have a couple contrarian opinions about a couple of 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.

58:58We do every make all our decisions, you know, with our dashboards. 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 don't 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 the dashboard. And maybe if they got really, really good at picking metrics, it would be fine. 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.

59:37But 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 or team of super data driven or company 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 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.

1:00:12Like, 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. One quick story on this. I remember really early on in my career, Adam Medros, who was the VP Rada distributor 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 okay with me saying this because this is my memory of this moment. He was just like, this is an obviously better thing. Like, just do it.

1:00:42Like, stop, stop it. Like, stop doing all the stuff that you're doing. Like, stop with these numbers. Look, whatever it was they're 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. 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 like, 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. Okay. Another topic that you have some interesting opinions about is product content.

1:01:15Very 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 and looking at it, they're 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.

1:01:56And 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. And they say, nothing I have in my toolkit makes sense for this moment. But I know what to do, because, you know, 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.

1:02:23And the point is the one -pager 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 roadmaps. So, like, why are you asking me for a road map? And then, you're the asshole who's sitting there being like, well, it's like a little more complicated than that. And, you know, 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.

1:02:50Bob, Bob. 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. 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, you know, it often loses the new ones. Because if you add 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. So if it's another just like, here's how to roadmap. Really, it's successfully.

1:03:20And it's like what everyone's already done. No, it's going to read it. So you always have to kind of have a new take. And with that 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 that my last role we would, you're, we all had your news letter. And we listened to the show. And then people would bring, I can't, I should have found a clip. But I can't remember. There were a couple of women's reviews. We would listen to a piece of it or find a article and say, like, oh, like, this could help or what if we did it that way?

1:03:55I think there was a newsletter article about Vigma and they had some templates. They're like product review template for Vigjam. 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 route. We should be doing it this way versus like, like, I think people assume these are the one way to do it or the innately will work at your company.

1:04:29And I really like your point, 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 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 in 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 get to do at this magical company?

1:05:02But again, if you view it as more like, here are all the tools that you can add to your toolkit and you pull them out in your next situation for which they can be useful. That's how I think about it versus like, 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 try 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?

1:05:34Should I try them, commented? But still, I think there's an implication. This is the way to do research. Here's the way to do, wrote my plan. Here's the way to purchase. But I think it's interesting that you also, yourself create a lot of content. You actually found a lot of value from being a, let's not call you content creator, because I don't want, I don't like being labeled as a creator myself. Someone once called me a product influencer on dive 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.

1:06:11Yeah. 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 a drift 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. 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.

1:06:52Also, building a personal brand is really helpful if you want, one of the things that I always wanted to do with my careers, try to make it so that I'm always employable. You know, I just didn't want to like, you know, I'm in the O8 grad, not to put my age out there. And it was a hard time. And so I've always had this in the back of my mind. Like, you know, you want to be able to have a solid career. 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.

1:07:26Because 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. And that's huge because if my job is hired, 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.

1:08:02And then, you know, especially if it's in a podcast medium, talk to somebody about it. And the process of doing that means that you're paying attention to what you're learning along the way. And like, so often we don't do that because we're busy working, we have our lives, we're just, you know, 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 down. Something that comes across in your content that you've somehow figured out is to avoid it being cringey and very thirsty for followers.

1:08:37And I think when a lot of people hear, build a personal brand, it's like, I don't want to. I know, I can't make it, it makes me ill even saying that. Yeah, okay. I mean, like, I never, I never thought of it. I wanted to think of it that way. And I'm just curious what advice you'd give to people that want to go down the threat without feeling, I guess one is just feeling like they're being cringey and to avoiding content people will be like, oh my god, I can't believe this stuff. Yeah, the like clickbait. Yeah. Tweet thread situation. You know, I think the step one is going to be cringe. Like your first 10, 20 however many posts are going to be bad.

1:09:14I would imagine if you listened to, 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 episode. Yes, with Shreya's, which I could see why it was so popular. Yeah, you so you started it and we're 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, like anything, you just have to get started. And it'll fade away eventually and you don't have to think about it.

1:09:46To 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 this 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 and 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 I those were real questions that I had, real processes that I was working on. And real advice that I needed at that time. And I think that's why it was valuable because I was actively a PM.

1:10:21In the way that like 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, for, you know, likes and chairs. I think there's some two really important points there that stood out to me. Your stuff is going to be terrible if you don't actually have any background or experience in the things you're just like pretending. It's like the, like you're, you're acting like someone that 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 it'll be like, okay, well, I did it for two months and I have nothing more to say.

1:11:02Right. Right. And then the other piece is there's a guest who shared this quote that is stuck with me from Einstein, which is something like seek not to be successful, but of value. And I find that that's really good framing for sharing stuff is 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 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 crammed or make fun of you or whatever because that's what they want to do.

1:11:48And maybe I'm not I'm not even going to get into psychology of that, 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. 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 that you use by people and sell problems. It's a really cool job.

1:12:16And 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, but the suit 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 even mentioned that just like it needs to feel really authentic and clearly for you is just like, there's just stuff I want to share because it's really interesting to me. 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.

1:12:49And I found it useful. And I just assumed other people might find it useful. So I did also learn and I wonder if you found this too is that 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 like more to learn about how to roadmap, how to prioritize, how to hire, how to talk to, how to have different conversations, performance reviews. 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 presence in your slides or whatever.

1:13:29And I just wrote out in my notebook like, okay, here's how 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 and I sketch out how I want the slides to go. And then I go into Google Docs and I actually make this line. And I was like some silly little thing and this person 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.

1:14:03And 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 stuff that is most interesting because it's something that maybe you're really good at that you don't realize. 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 round.

1:14:34Is there anything else that you want to share, touch on, think might be useful to leave folks with? I hope that people, I'm I hope is always the 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. I think that also that gets missed and 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 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.

1:15:08You 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. 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 bets by Annie Duke is the second one.

1:15:50I'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 enjoy the way that one is working. It just sits on my desk and I reference it real swell, especially as manager. I have it both under my laptop where I'm sitting and then also way behind there. And it's one of those popular episodes I've done with Claire. So it's folks have to listen to that one. I highly recommend she's incredible. Great choice.

1:16:23What is a favorite recent movie or TV show you really enjoyed? Okay, so my husband is in the industry as we say here in LA. 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. Well, 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 gave away, but let's touch on again. Yeah, it is what is the worst product that you've ever shipped? I think the best answers are ones and if I don't even care if someone listens to this and then I do this in an interview.

1:17:01People 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 know, you have some humor, your humble and you can point out when you've made a mistake, right? 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 they really like? One because I've seen you on Twitter.

1:17:34You're a future fit guy. Yeah, I am. I used it three times a week. Yes. Yes. I was also a future fit person. Love. 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. I don't need the accountability. So like, that's not a thing that I needed as an ex -athlete. So for me, that didn't serve me. And this is... 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. So that's one more of a funny one.

1:18:09And the second one, not to like get real niche, but I think good products or 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. 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 finished. The other favorite life motto that you either repeat yourself often, like to share folks find useful and just kind of living life.

1:18:50I'm sure there's models, I could say, that would be aspirational models. 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. 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 like you may as well be good at it or trying to get good at it. And that's always how, how I've lived my life. I so love that message. I always think about that. Final question. You are an Olympic speed skater, which I don't think people would know necessarily that's insane.

1:19:32My question is, is there some bad speed skating that would surprise people? That would be like, what? Oh, that is one I've never been asked before. The whole experience, I've learned, obviously, learned a ton from it. And I think what might surprise people about being a small sport athlete is that you, you have to think in four or eight year chunks. 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 a speed skating, I was a long track speed skater.

1:20:12It'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 that, perfecting something over and over again. 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 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.

1:20:45So much of what you just said would apply 100 % to product management. And I love that. Maggie, you are awesome. Two final questions. Working folks finding online if they want to reach out and maybe ask you any follow questions. And then two, how can listeners be useful to you? You can find me on Twitter for sure. I linked in, but just being of cringe, like I just can't get into the LinkedIn posting. LinkedIn's gotten better. I'd give it a shot. It's like actually pretty interesting now. Yeah. I'm thinking, I'm thinking about it. I go back to work in a couple of weeks and thinking about LinkedIn.

1:21:21But 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 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 guests are your, their roles you're hiring for just for folks that are listening and just like, hey, maybe I should go do that.

1:21:55There 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 great. 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. 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 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 Lenny's podcast .com.

1:22:29See you in the next episode.