YouSaid · the spoken record

Maggie Crowley

lines on the record: 95
first: 2023-11-05
most recent: 2023-11-05
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“Thinking about LinkedIn, 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.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. 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 speeds 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. And you learn how to grind. You learn how to focus.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“Sure, there's models I could say that would be aspirational models, but the real one is if it's worth doing, it's worth doing well. And 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 I've lived my life.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“Your whole team. It's fantastic. I'm really enjoying it. So that's one more of a funny one. And the second one, not to 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 or snow side quests. I'm a new mom. There's this app called pump log. 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.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“I use it three times a week. 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.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“I did. 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 know, you have some humor. You're 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.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 on TV. But I think my favorite one that I've watched recently was Slow Horses. Gary Oldman is incredible. Highly recommend.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“First, most common one is probably the presentation secret. 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. That's one. Thinking in bets by Annie Duke is the second one. 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 and it just sits on my desk and I reference it every once in a while, especially as manager.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. I think that also that 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 makes it all very entertaining. So I've always found a lot of joy in the job.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 presentation slides or whatever. And 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 the slide. And it 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 this took me 75% less time than it would have taken me otherwise. And I was like, I may do 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 a stuff.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, people can absolutely tell. And the other thing is there's a little bit of too cool for school mixed in here. And there are definitely people who will. Tell you your content is 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, 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 or for worse, like I love working in product. 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. It's all 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. But this is what I do all day long. So like I'd like to get better at it.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“So, yeah, first get over the fact that it's going to be cringe, it's going to be cringe, you just have to get started and it'll fade away eventually and you don't have to think about it. 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 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 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 is because I was actively a PN. And 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.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, the clickbait. Thread situation. You know, I think step one is going to be cringe like your first 10, 20, however many posts are going to be bad. I 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? Natural.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“Those things has been that 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. 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, 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 have if I wasn't, if I didn't have to write something down.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“Also, 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. 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 I've always had this in the back of my mind. Like 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 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. 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”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, it's probably the best thing I've ever done for my career. And I'm so grateful for the people whose idea was who supported me, especially a drift 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.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“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, like, how am I ever going to do that thing that they get to do at this magical company? But 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 when you're in a situation from 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-pager, the only way you can run an experiment is more like you can do it in many different ways.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“Love that one. Use that one all the time. And so, yeah, I mean, the 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.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“I mean, it's helpful. I think all of the, there's some people who create, I mean, there's many things at my last role. We all had your newsletter 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 moments where 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 like product review template for Fig Jam.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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 roadmap? And then you're the asshole who's sitting there being like, well. Like a little more complicated than that, and that was a fun take that I had, but I actually need to understand where we're doing because we're planning and I need to figure out what my budget is, blah, bl”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“Really, if you're going to make good content, 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, 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 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 I throw them out. 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'm”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. Like stop, stop it. Like stop doing all the stuff that you're doing. Like stop with these numbers, like whatever it was 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. And I've always thought about that, but like you can just do the obviously better thing.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. 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. One quick story on this. I remember really early on in my career Adam Medros, who was a VP Roddy TripAdvisor. We were in a room. We had this meeting called product review that was amazing when I first joined.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 an executive who's saying things like, oh, we're so data driven. We make all our decisions with our dashboards. To me, that says that the team is overemphasizing quantitative data at the expense of 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 via a 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.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. Sunk cost fallacy, just the worst. And it's because, A, 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”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“This is so dumb. I 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 decided we needed to do a rewrite red flag number one of a existing product and engineer who I'd worked with many times. We had a really good relationship. And this person was like, yeah, yeah, it's going to take six months. No problem. 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.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“Might be foreshadowing, but a question I ask in every product interview is what's the worst product you've 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. And I remember.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 none of that matters. Like I didn't know what I was like, it was just people would say the wildest stuff and I would sit there as a PM and just think What, like, 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. Like nothing goes the way you want it 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.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 in a bigger company. And so the why now is an important question to answer because if not, somebody's going to ask you. So you may as well think about it”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“I don't think these templates have to be very complicated. It's like background and context, the problem. 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 to smart people around you to take shots at it. I should have mentioned this earlier with the strategy. The first person I go to is 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 you need people to like poke holes in it”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“So, 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 a link off to all the different artifacts and research and things is helpful.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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 at 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.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“Okay, yeah, the one major, I don't think I have much to say about this that has 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 product design engineering, your little squad. And 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 a PMs do. A lot of people might say nothing. In theory, we write at least this document, right?”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“What do we do? Like, 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.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“And they're never the same. And the roadmap is just bloated with all of us 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 delayed, 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.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 there's a moment where you take this strategy and then you look at your roadm”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“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? 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.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“And we will know that the post PR department would be really unhappy with me. It's questions like if you're a director product somewhere, right? Maybe you're running a section of a business and its annual planning. We're in Q4. What are you going to do next year?”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I think, I mean, it's obviously. Product content gets really challenging because I obviously can't really talk about the stuff I'm currently working on.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“Okay, sure. 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 like it didn't really matter”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“Comes back to the reason why I write the document in the first place, and that's for me. So it's my homework to do my job effectively. I just make sure to share it. And I find that 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 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 some people that'll skim the upfront part and either say, yeah, that looks great or you're dumb. I hate this.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“I've had some because The actual content I end up writing a summary to go back to the Minto principle. I end up 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. Can kind of get the whole point and the suggestion on what I think we should do or what the strategy should be summarizable in that section. But it can go 20 pages just because if you really want to get deep in a competitor or there's interesting market dynamics, interesting technological changes that are happening, like sometimes I'm screenshotting 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 it can be all kinds of different things that you might want to put in there.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. 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.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 every product needs a strategy. Like every feature doesn't need a strategy, for example. You don't need to do this if you're working on a tiny slice of a product and you have user feedback. don't overcomplicate 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 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 right”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“I've only ever done it in like a loose Google Doc and then 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.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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 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.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source
“And then, what would you do? Like, take a swing at writing down your solution, what you would need to build, how might it work, anything that you have. This is where I would say three bullets maybe of 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 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.”
2023-11-05 · Lenny's Podcast · Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor) · IDENTIFIED FROM THE TRANSCRIPT · source