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

1. 0:00 – 4:06

   Maggie’s background

   1. MCMaggie Crowley0:00

      If you ever find yourself saying something like, "That's not my job," that's probably a thing you should do. And it- you know what? It probably isn't your job and it probably is someone else's job, and you can spend your life getting frustrated with that or you can just get over it and get the work done. And people who are willing to just get the work done will move faster, their products will be more successful, and they probably aren't carrying around all that anger and crappy emotion. Because as a PM, for better or for worse, and maybe this is 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, and you just have to, like, keep that optimism going and it's hard work. And part of it can be just like, "You know what? Let me take that on. I'll do this thing, I'll hop on this sales call, I'll implement this with the customer." You just have to do whatever it takes.

   2. LRLenny Rachitsky0:55

      (instrumental music) Today, my guest is Maggie Crowley. Maggie is currently vice president of Product at Toast. Prior to this, she was VP and head of Product at CharlieHealth, senior director of Product at Drift, director of Product at BevSpot, product manager at TripAdvisor. She's also got an MBA from Harvard Business School. She was also an Olympic speed skater, which is insane and incredibly cool. And in our conversation, we discuss the three most common threads across the best product managers that she's worked with, hired, and managed; how to very tactically write out a product strategy to share with your team and manager; why being data-driven is a red flag for product thinking; why product content you find online can be dangerous; her best advice for how to break into product management; also, the impact writing online has had on her career; and so much more. Maggie is amazing. I'm excited for you to learn from her like I did. With that, I bring you Maggie Crowley after a short word from our sponsors. This episode is brought to you by ProductRoadmap.ai and Ignition. ProductRoadmap.ai is the first AI roadmapping suite. It helps ensure roadmaps drive revenue by instantly aligning product with your sales and marketing teams to capture upsell opportunities. Built by early leaders from Rippling and Craft, it automatically identifies feature gaps from your CRM data and your customer conversations, adds them to shareable roadmaps easily prioritized by revenue impact, and then seamlessly closes the loop with sales reps via targeted notifications when feature gaps are closed. As part of Ignition's broader go-to-market operating system, ProductRoadmap.ai can also help create better handoffs and collaboration with product marketing teams by giving both teams the tools to research, plan, orchestrate, and measure the process of building products and going to market. Packed with integrations, AI automation, and communication tools, it's truly a one-stop shop for product and marketing to bring things from concept to launch. To sign up, go to ProductRoadmap.ai and use promo code Lenny to get 75% off your first year. This episode is brought to you by Composer, the AI-powered trading platform now with retirement accounts. Algorithmic trading has historically been reserved for the hedge fund elite. Now, with Composer, you can automate your trading with a library of over 1,000 strategies that are easy to understand and tweak using an AI assistant and visual editor. Composer is the first ever algorithmic trading platform where you don't need any coding experience. It includes a full range of trading indicators for you to get creative, and a Discord community of 2,500 traders to discuss your ideas with. Composer also has a powerful back tester to see the historical performance of your strategies, and you can then invest with a single click. Once you invest, Composer will automatically trade for you based on the logic of your strategy. With one billion dollars in trading volume and over one million trades executed, Composer already has many big time investors using the platform regularly. Head to composer.trade and use the code Lenny for an extra week of free trial on your Composer membership. That's composer.trade.

2. 4:06 – 9:33

   Three common traits among the best PMs

   1. LRLenny Rachitsky4:06

      Maggie, thank you so much for being here. Welcome to the podcast.

   2. MCMaggie Crowley4:10

      Thanks for having me. I'm super excited.

   3. LRLenny Rachitsky4:12

      You put out so much content across podcasts, blogs, tweets. I'm sure there's other things I haven't even seen. And so what I've done is I've scoured all of your content as much as I could to find topics that we could dig into in our conversation today. And I thought it'd be fun to start with how to become a successful product manager and what it takes to be a successful product manager, especially long term in your career. You've worked with a bunch of PMs, you've hired a lot of PMs, you've managed a lot of PMs. And so I guess the question is just what are some common threads you've seen across the best product managers?

   4. MCMaggie Crowley4:50

      Yeah, it's an interesting question, mostly because I've worked in, you know, startups, zero-to-one, scaling stage startups, enterprise, all that kind of stuff. And there's a lot of content out there, I think, on how those roles are different and how PMs are different across those different types of companies. But what I've seen is that there are some standard things that are the- the same across the role no matter whether you're a consumer, B2B, or startup, or a large- large company, and in particular about what sets PMs apart from one another. And the things that I look for when I'm hiring or when I'm looking for promotion, to promote people, or, you know, when PMs stand out even when you're not looking are three things. First, I think the best PMs are really good at breaking things down and simplifying things. Uh, so finding at any moment, like, what is the- really truly the only thing you need to do? Especially in a big company, there are eight million priorities. There's 700 OKRs, there's 25,000 projects you could work on, and teams will get bogged down in that complexity. Similarly speaking at a startup, you might think that it's easy to find the one thing to do, but at the same time, there's so many fires that are happening and so many things you could do in such a world of opportunity that even just picking one...... and sticking with it is really difficult. And so the best PMs not only can find the one thing to work on, but they can stay with that one thing long enough to actually finish it.

   5. LRLenny Rachitsky6:15

      I think that's a really interesting point, 'cause it sounds simple also just this idea of simplifying, but I think there's so much depth there, partly 'cause within simplifying is prioritizing. And that's, you can almost boil down the job of a PM as they're just prioritizing and telling people what is next. And so I think that's a really powerful point you're making.

   6. MCMaggie Crowley6:33

      Prioritization is a tough word, because there's so much wrapped up in that and what it means to prioritize.

   7. LRLenny Rachitsky6:39

      Mm-hmm.

   8. MCMaggie Crowley6:39

      And, you know, I've worked for people who wanted to understand the formula for prioritization, and why this thing, and, like, how can you prove that this is the right thing to work on, and not that thing? And then, you know, a week goes by, and then they're, they want to re-evaluate the priority, and they want to re-litigate the priority.

   9. LRLenny Rachitsky6:56

      Mm-hmm.

   10. MCMaggie Crowley6:56

       And so s- it's so much more than just a moment in time deciding, but it's the ability to stay with it, and to make sure that it continues to be the most important thing, that you finish it and actually see that it worked, um, and that you can get people to continue to stay excited and engaged in that project. Because I think a lot of when we talk about product, it's like, oh, what should you build, what should you ship? But then you actually have to ship that, and that can take a week, a month, three months, six months, a year. And so as a PM, your job is to stay on that and be the person who's beating that drum over and over again. And those, the best PMs are the ones who can do that and have the resilience and the kind of, like, energy to stay with it.

   11. LRLenny Rachitsky7:38

       Mm. Energy. That's a really important part of that. I'm gonna ask you how you suggest people get better at these things. So, either we can go into how you found i- you get better at simplifying.

   12. MCMaggie Crowley7:49

       Okay.

   13. LRLenny Rachitsky7:49

       Or we go through all three and then we can come back. Whatever you prefer.

   14. MCMaggie Crowley7:51

       Let's just do all three really quick.

   15. LRLenny Rachitsky7:53

       Mm-hmm.

   16. MCMaggie Crowley7:53

       And then we can dig in.

   17. LRLenny Rachitsky7:54

       Sounds great.

   18. MCMaggie Crowley7:54

       Um, so yeah. First one's simplifying. I think the second one has to do with this point about sticking with something, and it's following up on results.

   19. LRLenny Rachitsky8:02

       Mm.

   20. MCMaggie Crowley8:02

       So many people in the spec, or the one-pager or something, will say, "Okay, here's the metric that I care about. Here's what I want to move." Awesome. Maybe they'll even write a SQL query, get a dashboard going, figure out what the number is today. That gets you some extra points. But the really, really good PMs remember to follow up, because y- especially when you're in management, couple layers up in management, I'm not gonna remember to follow up on that feature. But if a PM comes back to me and says, "Hey, remember we did that thing? Here's what happened." I can't tell you how rare that is and how many times, as a leader, you might have to ask for that. And for the people you don't have to ask that of is one of the best things when I'm looking at PMs. And it's easy. Like, it's not hard to do that, especially if you've set up metric tracking or you know how to pull that information, or you have somebody who can help you get that. It's pretty easy to do, and it's h- really high, high value activity. And then the third thing, and I think maybe we'll talk about this later too, is that a phrase actually we were talking about, David Cancel, before we started, um, carrying the water. And this was a big theme, uh, when I joined Drift, and this is about how you can't be a good PM if you're not willing to do the hard, boring, un-glamorous work of customer support, sales, marketing, writing copy, project management. Like, you have to do that stuff. It's your job. No one else is gonna do it, because at the end of the day, you're responsible for outcomes and results. So, you're the person that has to do that, and if you're willing to do that work, that's what's gonna make your product successful, which is what makes you successful.

3. 9:33 – 11:14

   Strategy is an important but small part of the job

   1. MCMaggie Crowley9:33

   2. LRLenny Rachitsky9:33

      It's such an interesting list, because when you ask most people what you need to get better at to become a great product manager, it's always, "Communication skills, collaboration skills, vision, strategy." And feels like these are, like, input metrics to what is normally what people think about.

   3. MCMaggie Crowley9:50

      Those things, to me... Communication, super important. Um, analytical ability, really, really important. The ability to look at a, especially if you're doing something that has a, a user experience component, the ability to look at that and understand if it's gonna work and build up intuition around that, also really important. Those are things that I, I would see as sort of basics of the role. These are the things that make you great, great at the role. And strategy, to me, and hopefully we'll talk about strategy in a bit, it's one tiny slice. You do a strategy, but it's 5% of the work that you do. Yes, it's important, because you wanna get your strategy right, and you need to pick the right products. But, at the end of the day, the person who has a good strategy will not be as successful as the PM who ships more stuff, gets more reps, and has the ability to actually create impact. So, to me, you could be great at strategy, but if you're not good at this stuff and your stuff isn't getting out the door, you're never gonna be that great at the pro- at the job.

   4. LRLenny Rachitsky10:48

      Yeah. And impact is the other one. Everyone's always like, "How do you... What makes a great PM?" Oh, drive a lot of impact. And again, I think-

   5. MCMaggie Crowley10:52

      But they never say how.

   6. LRLenny Rachitsky10:54

      Right. Exactly.

   7. MCMaggie Crowley10:54

      It's like, "Cool. Let's do a strategy. Let's have impact." But then e- and when I was starting off as a PM, I was hearing this advice and reading about it, and I was sitting there saying, "Awesome. I want to create impact." And I'm looking at my job thinking, "How do- what... Now what?" Like, yeah. Impact. Let's do it. Where is it? How do I find it? (laughs) Someone help me.

4. 11:14 – 15:13

   How to get better at simplification

   1. MCMaggie Crowley11:14

   2. LRLenny Rachitsky11:14

      I love it. Okay. So let's, let's go back to these three. And I'm curious just what you found helps you become better at these things, and, and also just, like, an example if you can share. So, say, with simplifying. How do you, how does one build that muscle?

   3. MCMaggie Crowley11:27

      This is a tough one, 'cause some people... A, a broad generalization that I think comes up in things like when you're interviewing PMs for a job and you say things like, "Are they a simplifier or are they com- complexifier? Do they make things complicated?" The... And so some of it's a little bit of just who you are and how you think. But having said that, there's one tool that, that I use that I actually learned from my dad when I was in grade school, which is when you write something, for example, and a lot of what we do as PMs is written, when you write something, read it out loud. Literally just read the thing you wrote out loud, and half the time you'll realize it's way too complicated, doesn't make sense. Or, what happens is when someone comes to me and they say, "Okay, I'm working on this thing. You know, check it out. Can you read it?" I read it, and then I put it down, and I say, "What are you trying to say?"And 99% of the time they say, "Oh, users are really struggling with this problem. We found this in research and we think that the way to solve it is to do X." But that's not what the document says. And so my reaction is always, and if anyone who I've worked with is listening to this, they're gonna laugh, is always, "Just say that. You know, just say that thing. The thing that you said to me in conversation is the thing you should write. It do- there's no reason why your prose in a document has to be a certain way. We're not in school, right? Our goal is to get things done." So, those are just some simple tricks that I've used to help simplify what I'm, what I've already been working on. And as for how to boil things down and really find the most important thing to do, which is another part of simplification, I think the best thing you can do is just get as many repeti- reps in as you can.

   4. LRLenny Rachitsky13:08

      Mm-hmm.

   5. MCMaggie Crowley13:09

      Have people review your work and listen to them. There's a thing that, uh, that happens, I think, with, with PMs where you join a company and then all of a sudden it's like, "Oh, my leader doesn't, my boss doesn't know what they, what they're doing," in the, you know, highest paid person's opinion, and like the founder wants to swoop in and mess everything up. But those people had an insight on the market that you're in that made the company worth founding, and they probably know more than you and so you might wanna listen to them. And so find people who can review your work, listen to them and, and help, ask them to help you simplify.

   6. LRLenny Rachitsky13:39

      I will share a couple other things that came to mind as you were talking-

   7. MCMaggie Crowley13:41

      Yeah.

   8. LRLenny Rachitsky13:41

      ... 'cause this is like a very hard thing to teach and you kind of have to do it again and again.

   9. MCMaggie Crowley13:46

      Mm-hmm.

   10. LRLenny Rachitsky13:46

       And honestly, I, I had this one manager who taught me to simplify in my writing and strategy docs, one pagers and things like that, and I think that actually had a big impact on my newsletter success, is learning just to strip down as much as you can and cut anything that isn't necessary. So, there's a couple things that I, I'll share real quick. One is, there's this book I read called On Writing Well, that is one of the most impactful books for writing for me, and the whole book is like, I don't know, 20 chapters? And every chapter is more things you should cut from your writing. And they show all these examples of like, here's a before and here's an after, and all these words were cut and nothing changed. They're completely unnecessary. So, I think that book could help, and partly it's just like, what is not necessary? Like, you think all these adjectives are important.

   11. MCMaggie Crowley14:28

       Mm-hmm.

   12. LRLenny Rachitsky14:29

       Uh, another thing I found really helpful is this, the rule of thirds, I guess? The rule of three, of just like always having three. Like, try not to go beyond three when you're hearing like strategy bets or priorities or things like that. Just like try to keep things under three.

   13. MCMaggie Crowley14:44

       Yeah, it's a very sort of business school, ex-consultant point of view that I, I do agree with and share, which is a, there's always three things.

   14. LRLenny Rachitsky14:53

       Mm-hmm.

   15. MCMaggie Crowley14:53

       Or fewer.

   16. LRLenny Rachitsky14:54

       Yeah. (laughs)

   17. MCMaggie Crowley14:55

       Uh, never more than three things. You have to have a nice round couple, and if you have a fourth, you gotta figure out how to squish it in there 'cause it just-

   18. LRLenny Rachitsky15:00

       Yeah.

   19. MCMaggie Crowley15:01

       ... doesn't look right if there's four. Agreed.

   20. LRLenny Rachitsky15:02

       Yeah, even though I've, I've been guilty of more than three but-

   21. MCMaggie Crowley15:05

       Yeah. (laughs)

   22. LRLenny Rachitsky15:06

       ... but try, try hard to avoid it. The other thing is just like-

   23. MCMaggie Crowley15:07

       Yeah, like when you're using Notion and you have your three bullets expanding.

   24. LRLenny Rachitsky15:10

       Mm-hmm.

   25. MCMaggie Crowley15:11

       And there's sub-bullets, but at least you have that

5. 15:13 – 17:53

   Ownership

   1. MCMaggie Crowley15:13

      top line.

   2. LRLenny Rachitsky15:13

      Oh, yeah. (laughs) That's right.

   3. MCMaggie Crowley15:15

      Three. Yeah.

   4. LRLenny Rachitsky15:15

      Yeah. The other thing is I think it, there's just like a focus you need to get better, good at, just like people often wanna lump together a bunch of ideas and then every time you do that it just deletes everything. So, I think there's just a lot of power in like pick the thing, pick the thing that's gonna have the most impact and cut other stuff that may have some impact but is much less important.

   5. MCMaggie Crowley15:31

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

   6. LRLenny Rachitsky16:32

      Ownership. Such an important part of just being a PM. Uh, again, coming back to this interview I just did with an ex-Amazon guy, that's one of their principles at Amazon is just leaders, basically ownership, feeling like you have ownership of what you're working on.

   7. MCMaggie Crowley16:46

      I agree, but I, to me at least the word ownership doesn't have the same like-

   8. LRLenny Rachitsky16:50

      Yeah.

   9. MCMaggie Crowley16:50

      ... oh-shit feeling as-

   10. LRLenny Rachitsky16:51

       Mm-hmm.

   11. MCMaggie Crowley16:52

       ... you, you're making a bet.

   12. LRLenny Rachitsky16:53

       Mm-hmm.

   13. MCMaggie Crowley16:53

       Like you make a bet, that means you know that there's a chance that the thing you're working on is not gonna work out, and you still have to be the one to like do the thing, jump off the ledge, like drop in on the ski run. So, ownership to me never signaled that like risk-

   14. LRLenny Rachitsky17:07

       Mm-hmm.

   15. MCMaggie Crowley17:07

       ... um, that I think comes with being a PM.

   16. LRLenny Rachitsky17:10

       Good point. On the simplify concept, it reminds me at Airbnb, one of the core values at Airbnb for a time was simplify.

   17. MCMaggie Crowley17:18

       Mm-hmm.

   18. LRLenny Rachitsky17:18

       Is this idea that we should always try to be simplifying, and then it turned out the founders realized we're not actually great at this and it's unfair for us to say this is a value for not doing it, so they actually cut it as a core value, because their feeling was we shouldn't have aspirational values. We should reflect who we actually are, and they actually cut two different values to be more clear. Even though they still want to simplify, they're just like, "We're not, we're not actually good at this, so why are we pretending like we are?"

   19. MCMaggie Crowley17:45

       I think maybe I'm good at it on paper, but there's been many times where I've been in situations where things are not simple (laughs) and you just have to keep, keep

6. 17:53 – 19:39

   Examples of simplifying your work

   1. MCMaggie Crowley17:53

      fighting for it.

   2. LRLenny Rachitsky17:54

      Someone's trying to think about, okay, I want to get, uh, become better as a PM and I'm gonna try to start simplifying. What are examples of simplifying? Like, is it reduce your email length? Is it one pager focus? Like, what are, what are these buckets of things? And then also if there's an example of something you've simplified that comes to mind.

   3. MCMaggie Crowley18:12

      On what to simplify and more specifics, I would say-... anything can be simplified and shortened. Maybe another way to say short- shorten it. Definitely emails, like I ha- I read them sometimes. Don't love them. Make them shorter. Put the, the Minto Principle, um, is something that I would recommend everyone do, which is, like, put the, put the headline, the full conclusion first, and then your supporting argument second. Just-

   4. LRLenny Rachitsky18:36

      I have a newsletter post about that exact concept that people... That we'll link in the show notes, that gives you-

   5. MCMaggie Crowley18:40

      Okay, great. Fantastic.

   6. LRLenny Rachitsky18:41

      ... exactly how to use the Minto Pyramid Principle, yeah.

   7. MCMaggie Crowley18:43

      Yes, everyone should do that. A lot of new PMs fall into the trap of thinking that, that they should, like, have some sort of buildup. Don't do that. Just tell me whatever the thing is. Everyone will thank you. Doing things like that. Things like you said, limiting your strategy docs, your conclusions, your next steps to three things maximum. I would generally say, um, a rule of thumb would be pretty much every doc you write, you can delete the first two paragraphs that you, you've written. You don't need them. My dad, again, to go back to my dad, he, when I would write... And this sounds cruel, but I promise it wasn't. When I would write a paper for school, he would just, like, and this is back, we didn't really have computers or whatever. He would just, like, take away the first page.

   8. LRLenny Rachitsky19:24

      Mm-hmm.

   9. MCMaggie Crowley19:24

      And he'd be like, "Just start, just start here." Everything, he's-

   10. LRLenny Rachitsky19:26

       Yes.

   11. MCMaggie Crowley19:27

       ... he would go, "Everything on the first page is crapola. Don't use it." He would not-

   12. LRLenny Rachitsky19:30

       Such a-

   13. MCMaggie Crowley19:30

       And he wouldn't even read it-

   14. LRLenny Rachitsky19:31

       ... great point.

   15. MCMaggie Crowley19:31

       ... which would drive me crazy. Uh, (laughs) like, he would just, like, "Oh, that's crap. I don't care about that."

   16. LRLenny Rachitsky19:36

       Yep.

   17. MCMaggie Crowley19:37

       Um, so I would do that.

7. 19:39 – 21:37

   Maggie’s Slack support group

   1. MCMaggie Crowley19:39

      And then just get other people. Find... There's probably somebody around you that's good. And find people to edit your work and to look at it. Um, I have a little Slack workspace that has three people in it, me and two other women who are product leaders, and we oftentimes send each other our work still, and we say, like, "Hey, I'm struggling with this. Like, can you read it? Help me make it simpler. Can you he- help me fix this up?" And we do that for each other. So find a peer, you know, maybe who's in a noncompetitive space who can do that for you. I mean, I'm, I still use those people to help me.

   2. LRLenny Rachitsky20:10

      That is extremely cool. Can you talk more about this group that you have?

   3. MCMaggie Crowley20:13

      Yeah. (laughs) I don't, I don't know if it's a group. It's, like, three friends. Uh, shout out Alexa and Daphne. Um, yeah, I mean, the three of us all worked together when we were at Drift. We've stayed in touch, and I've just found that in order to be good at your job continuously, you need people who can help give you feedback, and the, and the more senior you get, the harder that is. And so having people who can give you another point of view, who maybe you can vent to if it's not appropriate as a leader, um, who can give you other experiences that they're going through has been incredibly valuable, and so we just have a little group chat that is focused on product.

   4. LRLenny Rachitsky20:49

      That is so cool. Any, uh, is there, like, a tip you could share for someone that wants to create something like this? Is it important for you to have worked with them before? Is Slack a good way to communicate? Anything there that's just like, "Oh, yeah, here's a cool tip"?

   5. MCMaggie Crowley21:00

      Slack just worked for us 'cause that's where we are during the day, and I think having easy access to it was important. You could probably use WhatsApp or a groups of, literal group text. There are small community, there was one, I worked in healthcare for, you know, a, a year and a bit, and there's a Slack community that somebody organized for heads of product in healthcare startups, uh, that is similar. It was really, really powerful and, and a really great space to be in. And so you just have to kind of suss out where these things are. You work with amazing people, and there's people around you who are gonna become your friends. And so keep an eye out for them and keep in touch with them when you leave a job, because you never know when your, when they might become your little

8. 21:37 – 23:23

   Following up on your work

   1. MCMaggie Crowley21:37

      Slack workspace.

   2. LRLenny Rachitsky21:38

      Ooh, I love it. Okay. I'm glad we talked on that. Okay, back on track. The second bucket you described is following up on results. How do you... Is it just do that? Is there anything more you can add there?

   3. MCMaggie Crowley21:49

      I put reminders in my calendar. I mean, yeah, it's just do that. But, like, if you're launching a product, usually, you know, you release something and you have that initial push of a couple of weeks where you're finding bugs and you're, maybe you're pulling metrics and everyone remembers it. Then I would remember two weeks after that, a month after that, six months after that. Put a reminder in your calendar to check your dashboard or check the metrics or check whatever it is that you were doing. A, you won't forget, and then share them with whoever might care about it. Um, and it's as simple as that.

   4. LRLenny Rachitsky22:20

      And is the reason this is one of the three things you think are most consistent across great PMs that it helps your manager see you like, "Wow, Maggie's so on top of everything"? Or, is it more that you learn from that experience and drive more impact? Or is it both?

   5. MCMaggie Crowley22:36

      It's definitely both. I, I don't... I'm not gonna pretend like if you're just great at your job quietly that you're gonna get what you want, right? You're not, just if you're toiling in the background doing a great job, getting results, if you have a great manager, maybe you'll be successful. Great managers are few and far between, and I, I'm of the opinion that I never wanted to rely on someone, someone else to get what I wanted. And so I would always make sure to share that, always make sure to share my progress, because I didn't want to leave it up to chance that someone would notice. So I would, I would suggest doing it for both reasons. Um, and that's one of those things that, like, you know, people want to pretend that everything's perfect and we're all great and, and we're always gonna get what we want and always gonna get that promotion, but you have to work for it, so.

9. 23:23 – 26:31

   PM time horizon

   1. LRLenny Rachitsky23:24

      I, I love that point. It reminds me, one of the, what I find one of the most important, uh, traits of a great product manager is they create this aura that they've got this. They put something on their plate and they, they're not gonna drop it. That the threads, threads are not gonna be forgotten. And this connects to me there. They feel like Maggie's gonna tell me what happened with this experiment. I could not have to, I don't have to think about it as a manager.

   2. MCMaggie Crowley23:45

      Yeah. That's a really good point. A- and then the, this, you mentioned this a little bit ago, the side benefit is that you learn more.

   3. LRLenny Rachitsky23:53

      Mm-hmm.

   4. MCMaggie Crowley23:53

      You know, you, you'll go back and learn why something happened or why it didn't happen, and the more that you follow up on what you've been doing 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 a PM who's shipped 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.

   5. LRLenny Rachitsky24:19

      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. They're like, "Oh, my God. I've been a PM for two years. I'm not 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?

   6. MCMaggie Crowley24:39

      I, I would say sim- 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. Uh, I had no PM background. It was after, uh, business school. And I left that, those two years thinking like, "Yeah. I've worked on four different teams over the two years. I've shipped all this stuff, like, I'm good." Went to a startup. Was bre- 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, the 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 gonna go to learn." And so then, you know, two more years, so that's five years until I really felt like I knew what I was doing and that's because then you just, 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- in and out of startups, but to me, staying at that st- uh, when I was at Drift, I was there for almost four years. I got to see two or three cycles of the same product and that, I learned more from that than I did out of the, you know, year or so I spent doing other things each at a time because you got to see the res- the consequences of your decisions and that's rare and people, you know, myself included, of course you want to get promoted, of course you want to, you know, move up. You know, I'm ambitious. Lots of people are ambitious. But for better 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.

10. 26:31 – 27:37

    Staying in your role vs. trying a new opportunity

    1. MCMaggie Crowley26:31

    2. LRLenny Rachitsky26:31

       So is that advice you often give of go deep into a company or a product versus just bounce and try a bunch of different companies or it depends?

    3. MCMaggie Crowley26:39

       It depends. There are lots of really good reasons to bounce. I've done it. Um, many people have done it. But I, I was surprised at how much I value that experience of having stuck around for a while and how much I learned from it was something I hadn't expected going into it, especially because you don't hear that point of view as much, or at least 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.

    4. LRLenny Rachitsky27:17

       Yeah. I, at my first job, I was there for nine years and then I started a company for a year and a half and then we sold to Airbnb and then I was at Airbnb for seven years. So I'm very much-

    5. MCMaggie Crowley27:25

       That's incredible.

    6. LRLenny Rachitsky27:25

       ... 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 pros and cons. But there's so many pros to that, so many reasons. Okay.

11. 27:37 – 28:56

    The importance of “carrying the water”

    1. LRLenny Rachitsky27:37

       Let's, uh, 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.

    2. MCMaggie Crowley27:43

       Yeah. This one, there's no tips and tricks. It's just do the work. Um, if you ever find yourself saying something like, "That's not my job," that's probably a thing you should do. And it, you know what? It probably isn't your job and it probably is someone else's job and you can spend your life getting frustrated with that or you can just get over it 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, 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, 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, and 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, to keep people amped for that thing and part of it can be just, like, "You know what? Let me take that on. You know, let me grab that, whatever. I'll do this thing. I'll hop on this sales call. I'll implement this with the customer." You just have to do whatever it takes.

12. 28:56 – 31:42

    Pros and cons of the PM job

    1. MCMaggie Crowley28:56

    2. LRLenny Rachitsky28:56

       It reminds me of, uh, 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. Can you speak to that?

    3. MCMaggie Crowley29:12

       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 the user experience. Obviously there's a lot more complexity in that role. Design, you're amazing. Engineering, you're amazing. Uh, TL;DR caveat, whatever. But as a PM, you don't have that thing, right? Like, it's not like, "Oh. My job is just to write the one pager." Like, that's not true. Your 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 could 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 gonna 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.

    4. LRLenny Rachitsky30:17

       It reminds me of another interview you did where you talked about how a lot of the PM job sucks-It's not as glamorous as people often think and the most of the job is these really boring, annoying things. I guess is there anything you want to add there, just like, you know, a lot of people see, 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.

    5. MCMaggie Crowley30:41

       It's just one of those things that like people, and when I joined product it was just sort of becoming a cool job. It wasn't like the hot job on campus when I was in business school, that was more like private equity venture capital. And now there's a sense of cache around it. But again, it comes back to the 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 a, there's a lot of bullshit work you have to do. You know, again, project management is one everyone hates on. QA is a really good one. You 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, you know, find users. All that stuff is stuff that you should be able to do and none of it is above you.

13. 31:42 – 34:36

    Advice on landing a PM role

    1. MCMaggie Crowley31:42

    2. LRLenny Rachitsky31:42

       If someone is listening and they're not a PM and they are not convinced to, to not get into product management, they still want to become a PM, what is your best advice for someone that is trying to get into product management about how to actually break into product management?

    3. MCMaggie Crowley31:55

       I thought about this one a lot and I, I consulted the work, the Slack workspace team.

    4. LRLenny Rachitsky32:01

       Mm. Mm-hmm.

    5. MCMaggie Crowley32:01

       Because it's been a, it's been a long time since I tried to get into product and so I didn't know, you know, what was going on these days because it's hard, and I hadn't, I didn't, I don't know if things have changed. You know, I went to business school and that's how I got in. There was a program that, that took MBA students. I think there are some entry level programs out there at big tech companies if you can get them. I think they're really hard to get 'cause they're very few and far between. And so the most common two paths that I've seen are people who switch laterally within a company, again, challenging but can be done, or people who join startups. So when I was at my last startup, I did hire someone who was coming out of business school who hadn't been into product into a PM role, and like I can't say I wouldn't do it because it was awesome and she was amazing, but it takes a lot of work. The reason why people don't do it is 'cause as a manager it takes a lot of work because you, 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, in a WeWork in person to help her onboard really quickly into the role, which was so rewarding and I loved every second of it and I wish I could do that again and again and again. Um, but to get that, she basically just hounded me. Uh, 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. So I don't know. I don't know if there's a reliable, if there's a reliable path that I can say like this is what my advice would be other than, you know, try a startup network, see what you can do.

    6. LRLenny Rachitsky33:33

       And you've made out this point elsewhere which I think is an additional key piece is once you have a PM title on your resume everything gets easier 'cause 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, I'm, like I'm not, this isn't the role. It's like rarely that, that someone wants someone that's never been a PM.

    7. MCMaggie Crowley33:51

       Yeah, and I, 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 'cause they're, you know, if they're deciding between roles and they have an opportunity to do something and my advice is always if you can get someone to stamp you with the product manager role, take it because to your point, it's what we screen on. It's for, for better or for worse 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 'cause you can get in and then you can talk about your experience because then the second question I have is what have you shipped? Right? So it's like have you been a PM before? What have you shipped? And it's fascinating how quickly people can't answer that question and the people who can are always several steps ahead of the people who

14. 34:36 – 39:55

    Step-by-step process for writing your product strategy

    1. MCMaggie Crowley34:36

       can't.

    2. LRLenny Rachitsky34:36

       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. A lot of people are also just confused what is, what is strategy? How do I get better at strategy? How do I describe a strategy? And you have a really s- 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?

    3. MCMaggie Crowley35:04

       Sure. Yeah, an- another thing that happens and I'll, I'll give, I'll give the outline, but another thing I hear especially as you get further in your career and unfortunately if you're maybe an underrepresented person in tech is that you need to be more strategic. And so that's feedback that almost always happens especially if you're a woman in product in tech who's knocking at the door of a leadership role. You've probably gotten that feedback. And so I made it my mission to figure out like what the heck is this thing? 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 it in the background because I, I had an engineer who I worked with who really wanted to understand why we were doing what we were doing and he was not satisfied with sort of a surface level answer and he was just pushing and pushing and pushing. And so what I did was I just wrote out a Google doc and I started with like okay, and not fancy, these are just bullets. What is the mission? Like what is the point of the company? What are our goals? Maybe we have a, 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 mar- our point of view on the market, who are our competitors, you know, a SWOT analysis, key risks that we might be facing. Just dump that all on paper.... then what are the current quarter's business goals or what- however you do planning, like what are the current things that your company's working on? Then I put in, all right, that's sort of the context that we're operating in. Then I wanted to understand where are ... so what is an honest accounting of the current state of your product, you know, the business overall and then the specific area that you're working in. What works, what doesn't work, what are, what are your customers saying? Bottoms up feedback, users, customers, teams.

    4. LRLenny Rachitsky37:01

       Hmm.

    5. MCMaggie Crowley37:01

       What is your support tickets? Get that all out on paper. And then really importantly, where are your technical hurdles? Like what are, what are the big pieces of tech debt, you know, what are, what are your engineering and technical teams always harping on that they wanna invest in, you know, are there some, like, big things coming down the pipe that you need to think about? Just get everything on paper. And then usually in the process of writing all that down, you'll start to see, okay, I kind of get where we are, I kind of get what the challenge is, and then you write a section that's like, what's the opportunity? From all of that, what's gonna bubble up as the top one or two opportunities for your team? Where do you wanna play? Where can you win? You know, where's the unique ... based on, like, your unique competitive advantage, where do you think you all should be and why? And then based on that opportunity, what are the challenges, right? So like, what's gonna be the hardest about taking advantage of that? What has to be ... another way to frame it is, you know, what has to be true about the world for that to work? Um, that's one that's been helpful. 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. Uh, and then a plan. Like, if, 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, 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's no, there should not be any secret, and you should be able to walk all the way from your company's mission down to the individual priority on your team and see the logic chain and why you got there. And if anyone doesn't agree with it, they can call out where their, where their 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, 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."

    6. LRLenny Rachitsky39:17

       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-

    7. MCMaggie Crowley39:23

       There's not. It's just ... I've only-

    8. LRLenny Rachitsky39:24

       ... Okay.

    9. MCMaggie Crowley39:24

       ... ever done it in, like, a loose Google Doc and then, you know, it just grows and, and changes. Um, I can, I can maybe try to write up those bullets.

    10. LRLenny Rachitsky39:32

        Okay. If you-

    11. MCMaggie Crowley39:32

        But it's just, like, I just make headers and then I just start dumping content in.

    12. LRLenny Rachitsky39:35

        Yes. That's all people need.

    13. MCMaggie Crowley39:37

        Yeah. (laughs)

    14. LRLenny Rachitsky39:37

        If you end up creating that before this comes out, we'll throw it in the show notes.

    15. MCMaggie Crowley39:40

        Okay.

    16. LRLenny Rachitsky39:40

        And if not, people can just bother you on Twitter and ask, "Maggie, where's that template that we talked about?"

    17. MCMaggie Crowley39:44

        Yeah. I will, I'm happy to, like, write it on a piece of paper and take a s- take a photo of it and send it around.

    18. LRLenny Rachitsky39:48

        There you go. Just make it really grainy and like an artifact.

    19. MCMaggie Crowley39:52

        Yeah.

    20. LRLenny Rachitsky39:52

        We found Maggie's template. Uh, this

15. 39:55 – 46:29

    Not every feature needs a strategy

    1. LRLenny Rachitsky39:55

       is awesome.

    2. MCMaggie Crowley39:55

       (laughs)

    3. LRLenny Rachitsky39:55

       So, I've never heard of a version of this with so much depth into the landscape, and I think that's so smart because so much of conflict and disagreement comes from you just don't have the same information, or the manager, exec, whatever is like, doesn't think you have the information. So, if you just lean into, "Here's everything that I know and here's what's happening, and if you disagree with this, cool, tell me," and then they'll change the plan.

    4. MCMaggie Crowley40:17

       Right.

    5. LRLenny Rachitsky40:17

       Um, yeah.

    6. MCMaggie Crowley40:18

       And p- part of it's also that typically speaking, when you're doing a strategy, you're doing it at a, 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 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, 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 gonna do the right thing. For some reason, I'm always paranoid that, like, other people have more information or are, like, doing it better than I'm doing it, and so I was like, okay, I have to wr- write it all, 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 and, like, you'll run into the same problems you run 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.

    7. LRLenny Rachitsky41:33

       So, along those lines, I was gonna 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 s- any guide?

    8. MCMaggie Crowley41:46

       It's long.

    9. LRLenny Rachitsky41:47

       Okay.

    10. MCMaggie Crowley41:47

        It gets real long. Like-

    11. LRLenny Rachitsky41:48

        Like, what is long?

    12. MCMaggie Crowley41:50

        I've had some ... 'Cause the, the actual content I end up writing a summary, to go back to the Minto principle, I end up, like, doing the whole thing then putting a summary at the top so that there's one within the first above the fold, if you will-

    13. LRLenny Rachitsky42:04

        Mm-hmm.

    14. MCMaggie Crowley42:04

        ... 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 summarizable in that section. But, like, it can go 20 pages just because if you really want to get deep in a competitor or there's interesting market dynamics, interesting technolo- technological changes that are happening, like, I, 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. There could be all kinds of different things that you might want to put in there.

    15. LRLenny Rachitsky42:37

        ... and you made the point that it's not like you expect people to read this whole thing. There's the summary that gives them a conclusion, and in theory, if they want to really dig into it, they can. But I guess, how do you find that balance of writing everything you know and making it so long that no-one's ever going to read it to like, here's, this is actually going to be useful to someone and plus here's a summary?

    16. MCMaggie Crowley42:58

        It comes back to the, 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 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 th- I find that those people will engage pretty deeply. Um, 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, it looks great," or, "You're dumb, I hate this." I'm like-

    17. LRLenny Rachitsky43:45

        (laughs)

    18. MCMaggie Crowley43:45

        ... "Okay, sure." There's always those people. So, it d- 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 it can facilitate a conversation, so, like, it didn't really matter.

    19. LRLenny Rachitsky43:58

        This episode is brought to you by Eppo. Eppo is a next generation A/B testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams. Companies like Twitch, Mural, ClickUp and DraftKings rely on Eppo to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features and Eppo helps you increase experimentation velocity while unlocking rigorous deep analysis in a way that no other commercial tool does. When I was at Airbnb, one of the things that I loved most was our experimentation platform, where I could set up experiments easily, troubleshoot issues and analyze performance all on my own. Eppo does all that and more with advanced statistical methods that can help you shave weeks off experiment time, an accessible UI for diving deeper into performance, and out of the box reporting that helps you avoid annoying prolonged analytic cycles. Eppo also makes it easy for you to share experiment insights with your team, sparking new ideas for the A/B testing flywheel. Eppo powers experimentation across every use case, including product, growth, machine learning, monetization and email marketing. Check out Eppo at GetEppo.com/Lenny and 10 X your experiment velocity. That's GetE-P-P-O.com/Lenny. Is there an example of a strategy you were thinking about recently or that you worked on in the past just to give people something concrete of, like, here's what Maggie thinks of as a, uh, question she's gonna develop a strategy around?

    20. MCMaggie Crowley45:28

        Yeah, I think, I mean, there's obviously this is where it it, product content gets really challenging because I obviously can't, can't really talk about the stuff I'm currently working on-

    21. LRLenny Rachitsky45:36

        Just tell us all of the secrets-

    22. MCMaggie Crowley45:37

        I, uh, yeah. (laughs)

    23. LRLenny Rachitsky45:37

        ... and already we'll know.

    24. MCMaggie Crowley45:38

        Yeah. The, the-

    25. LRLenny Rachitsky45:39

        It'll be between us.

    26. MCMaggie Crowley45:39

        ... Toast PR department would be really unhappy with me. Um, it's questions like, you know, what, 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 gonna do next year? How do you answer that question? What do you put, how do you back up your, your choices for that? You use a, 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? Um, 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 it, yes.

16. 46:29 – 48:09

    The value of working through the process

    1. MCMaggie Crowley46:29

    2. LRLenny Rachitsky46:29

       Awesome. This reminds me a little bit of a, just this, I keep mentioning this chat with Bill Carr that I had who was an early Amazon exec and how the narrative approach at Amazon, one of the benefits of that and the reasons they go there is partly for you to just realize this is a bad idea before anyone even needs to give you feedback-

    3. MCMaggie Crowley46:47

       Yes.

    4. LRLenny Rachitsky46:47

       ... and that's why they force you to write six pages (laughs) in depth about your idea, and then it goes in these concentric circles through the company and ideas 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.

    5. MCMaggie Crowley47:00

       Yeah, I, 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 through this exercise and you're like, "Okay, I know exactly what my three things are that I want to work on," then you, there's a moment where you take the strategy and then you look at your roadmap. And they're never the same, and the roadmap is just bloated with all this random stuff that, like, "Oh, well, we have to adapt 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 gonna do the thing." And then all of a sudden you've got 90% of your resources committed to things that don't track against your strategy, and it's a really interesting moment as a leader especially to sit there and go, "Well, what do we do?" Like, what do you do when you, when you have that problem and, and especially if you're a PM and you probably don't have the agency to say scrap the entire roadmap and work on my new strategy, but at least it, 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.

17. 48:09 – 54:16

    Maggie’s one-pager doc

    1. LRLenny Rachitsky48:09

       I'm gonna summarize the template real quick and then I'm gonna have another question kind of along the lines. 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, 'cause oftentimes it's a little more specific if you're working on a, like a product team strategy.

    2. MCMaggie Crowley48:24

       Yeah.

    3. LRLenny Rachitsky48:25

       Then there's a landscape of what's happening. So you include competitive, like, SWOT 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-

    4. MCMaggie Crowley48:41

       Mm-hmm.

    5. LRLenny Rachitsky48:41

       ... as a team/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. "Where we could place bets." Then, challenges of doing this. "What needs to be true for this to be possible." And then you act- 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, get sign off from execs. Step two-"

    6. MCMaggie Crowley49:20

       Yep.

    7. LRLenny Rachitsky49:20

       "... resource the team. Step three-"

    8. MCMaggie Crowley49:22

       Yes.

    9. LRLenny Rachitsky49:22

       "... start on this design research sprint."

    10. MCMaggie Crowley49:26

        Pretty much.

    11. LRLenny Rachitsky49:27

        Awesome. All right, amazing. Somebody will create this template if you don't end up doing it.

    12. MCMaggie Crowley49:30

        Yeah. (laughs)

    13. LRLenny Rachitsky49:32

        There's another-

    14. MCMaggie Crowley49:32

        I hope somebody does.

    15. LRLenny Rachitsky49:34

        Okay. That'd be awesome. If they do, uh, I will tweet it and we will put it in the show notes.

    16. MCMaggie Crowley49:39

        Great.

    17. LRLenny Rachitsky49:39

        So many promises already from this podcast.

    18. MCMaggie Crowley49:41

        (laughs)

    19. LRLenny Rachitsky49:42

        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.

    20. MCMaggie Crowley49:52

        Okay. Yeah, the one-pager, 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 S- a spec, a PRD, a one-pager, I don't even know what else people call it, it's the, you know, the document that you use to define the thing that you're doing as a product team and that means like product design engineering, like your little squad. And what I think is really useful about this process is that it's the PM's artifact. So, you know, designs, designers produce designs, engineers write code, you know, what do PMs do? A lot of people might say, "Nothing." Um, 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 s- the first part which is like, what is the background and context? What is the problem? Why does it matter? And why does it matter now? And if you get those things right, the rest gets really easy, but it gives you a chance as a PM to, 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, um, 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- it can become the home base of the decisions that you make along the way. So, I think it's best when you have those sections and then also best when you, you write down, "Okay, on this day, we made this decision." Or, "We decided not to do this." Or, "We decided only to solve this part of the problem, not this part of the problem." Keeping a running list of that and the link off to all the different artifacts and research and things is, is helpful for a team.

    21. LRLenny Rachitsky51:52

        So, just to summarize, what would be the headings again just so if someone's taking notes and wants to create their little template?

    22. MCMaggie Crowley51:57

        I don't think these, 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 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've 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 'cause that's how we- 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.

    23. LRLenny Rachitsky52:48

        The why this matters now point is so interesting. I don't often hear that, and I think it's such an important part of specs and plans and strategies because there's so many things you can do and there's certain things that are perishable that you can only do now, that if you don't do now you miss a big opportunity. And so I think that's a really interesting element that most people don't include and it reminds me of, I think I've done enough podcast episodes now where I'm just connecting all these things as people are talking-

    24. MCMaggie Crowley53:14

        Yeah. (laughs)

    25. LRLenny Rachitsky53:14

        ... it's like this John Nash thing happening where, um, Kari, the founder of Linear talked about this concept of side quests as a founder-

    26. MCMaggie Crowley53:23

        Mm-hmm.

    27. LRLenny Rachitsky53:23

        ... 'cause he's so good at staying focused and I was just like, "How do you stay focused and just get stuff done when you have so many people coming at you?" He's just like, "There's the main quest and then there's the side quests. And side quest I don't need to do right now. There's the main quest which is build a really successful business."

    28. MCMaggie Crowley53:36

        Yeah.

    29. LRLenny Rachitsky53:36

        And I feel like this is a good example of that in action.

    30. MCMaggie Crowley53:39

        Yeah, I love his take on, on quality and taste too. Uh-
18. 54:16 – 55:44

    Contrarian corner

    1. LRLenny Rachitsky54:16

       Anyway, I'm gonna move on to a different topic and this might become a new thing that we do, and I'm gonna call it Contrarian Corner. I asked you if you have contrarian opinions about things before we started recording this episode, and you had some really good ones. So, there's a couple topics I'm gonna chat about and we'll see if this becomes a recurring theme and you're, uh, laughing and nodding your head. What are you thinking as I say this?

    2. MCMaggie Crowley54:39

       I'm thinking about when I had a podcast, you would do a show on a topic and we would-... click the end recording button. And then every single guest would be like, "I had no idea what I was doing. I made it all up. It was waterfall." They were 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? Like, we just talked about this, this framework, we just talked about this thing and, like, that's how you're supposed to do it." And then they would get off of, get off the, 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, I hope that you get more of those takes in this part of the, part of the show.

    3. LRLenny Rachitsky55:18

       I'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 just like, "Here's things that go wrong," versus the newsletter. So, I'm just like, "Shit, I need to do more

19. 55:44 – 58:33

    The worst product Maggie ever shipped

    1. LRLenny Rachitsky55:44

       of that. ) So, I love that you mention that and, and let's, yeah, let's see what we can get into. Uh, but I guess maybe before we get there, is there an example of something that didn't go right, just along the lines of (laughs) some sort of failure/mistake?

    2. MCMaggie Crowley55:59

       I might be foreshadowing, but, um, a question I ask in every product interview is, uh, "What's the worst product you've 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, 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... (laughs) 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 gonna call that out, but we wanted, we decided we needed to do a re-write, red flag number one, of a existing product and, you know, engineer who I'd worked with many times, we had a really good relationship, and this person was like, "Yeah, yeah, yeah, it's gonna take six months." Like, no problem. Core part of the product, been around for 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. It still wasn't done. It almost never... Like, it, it went on for so much longer than it should have. It took us forever to get to feature 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, 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 you have it.

    3. LRLenny Rachitsky57:34

       And did not work out, or was it a huge success in the end and it changed the trajectory of the business?

    4. MCMaggie Crowley57:39

       Absolutely not. But you know what? I didn't get fired, so, like, it's fine.

    5. LRLenny Rachitsky57:43

       I feel like I've gone through those experiences and then, like, three or four years later, it's like another, "Maybe this re-write and redesign may work, 'cause just we haven't updated this thing in a long time."

    6. MCMaggie Crowley57:52

       Just don't do it. Don't re-write. If anyone ever tells you to do a re-write, don't do it. A side-by-side re-write, nope.

    7. LRLenny Rachitsky57:59

       Yep. I've never had a... Like, what I run into is, once you get too far down a redesign/re-write, everything one's building in that new world, and then you launch it and the experiment's negative and then it's just like, "Well, we just gotta launch it. We're gonna claw back. We're gonna, we're gonna figure out how to get back to neutral someday."

    8. MCMaggie Crowley58:13

       Yeah.

    9. LRLenny Rachitsky58:14

       Yeah.

    10. MCMaggie Crowley58:15

        Yeah. Don't do that.

    11. LRLenny Rachitsky58:16

        Good times. All right. Well, maybe we'll start a failure corner. That could be a new-

    12. MCMaggie Crowley58:20

        Yeah. (laughs)

    13. LRLenny Rachitsky58:21

        ... segment. We may have a little sound and theme music. But this time, we have contrarian corner, and you have a couple contrarian opinions about couple of topics. The first is product management.

20. 58:33 – 1:01:10

    Why being “data-driven” is a red flag

    1. LRLenny Rachitsky58:33

       What is, uh, something that you believe about product management that maybe other people are less convinced by?

    2. MCMaggie Crowley58:39

       The one I like to have in this area is that people who are really excited about being data-driven, to me, that is oftentimes a red flag for their product thinking. Especially if it's, you know, an executive who's saying things like, "Oh, we're so data-driven. We do ev- we make all our decisions, you know, with our dashboards." To me, that says that the team is over-emphasizing quantitative data at the expense of qualitative data, and they're not using good judgment. Uh, 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 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. But most PMs, most jobs, most products, you're gonna 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 that you had.

    3. LRLenny Rachitsky59:51

       So, the takeaway there is just, like, be careful when someone is saying they're so, they're super data-driven. Our team is super data-driven, or our company's super data-driven.

    4. MCMaggie Crowley1:00:00

       Yeah. And maybe it's true, right? And that's great. Like, I'm not saying that you don't need data. You, you absolutely do need to instrument your product and understand if it's working at scale. But you can't forget that the, 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, one quick story on this. I remember really early on in my career, Adam Medros, who was a VP product at TripAdvisor, 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 kind of, I hope he is okay with me saying this, 'cause 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 that they were doing. Like, "If it's obviously better, if it's logically better, use your good judgment and do that thing, and, like, let's move on." I've always thought about that, that, like...... you can just do the obviously better thing.

    5. LRLenny Rachitsky1:00:58

       Yeah. I love that. I, I pull that card sometimes. But, um, ye- I li- I think you almost have to do it that way of just like, "Okay, everyone, this one's just, like-"

    6. MCMaggie Crowley1:01:06

       Yeah.

    7. LRLenny Rachitsky1:01:07

       ... "obviously a good idea. Let's just do it."

    8. MCMaggie Crowley1:01:08

       Yes.

    9. LRLenny Rachitsky1:01:09

       "Enough research."

21. 1:01:10 – 1:14:27

    Content creation

    1. LRLenny Rachitsky1:01:10

       Okay. Another topic that you have, uh, some interesting opinions about is product content, very close to our hearts, both my heart and your heart. Uh, do share.

    2. MCMaggie Crowley1:01:20

       Really, if you're gonna make good content, like you have to sanitize and frameworkize the thing that you're, that you're working on. And then slowly, I think for a lot of people who are reading it and looking at it, they, it, like their thinking starts to become, "Well, look how well I did this framework. Look how well I implemented this thing." And they lose touch with the point, which is like creating impact. And so all of this content makes it really noisy and then makes people think that like, "Oh, if I just do these things, that I'll get what I want, and then 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, you know, 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, 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, uh, 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, 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 'cause we're planning, and like I need to figure out what my budget is, blah, blah, blah."

    3. LRLenny Rachitsky1:02:52

       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, yeah, it often loses the nuance. 'Cause if you add all the nuance, no one's gonna even read it 'cause it's so complicated and long.

    4. MCMaggie Crowley1:03:13

       Right.

    5. LRLenny Rachitsky1:03:14

       And then the other point of, there's also just like, it has to be interesting.

    6. MCMaggie Crowley1:03:18

       Mm-hmm.

    7. LRLenny Rachitsky1:03:18

       So if it's another just like, "Here's how to roadmap really successfully," and it's like what everyone's already done, no one's gonna read it. So you always have to kind of have a new take, and with that comes like, "Ah, it's not actually always true. I just kind of wanted people to react to this idea."

    8. MCMaggie Crowley1:03:32

       Yeah. Yeah, I mean, it's helpful. I think all of the... there's some people who create... I mean, I... there's many things. At my last role, we would... you're... we all had your newsletter and we listened to the show and then people would bring... I can't... I should have found a clip, but I can't remember. There were a couple moments where we w- we would listen to so- a pie- a piece of it or find a, a 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.

    9. LRLenny Rachitsky1:03:58

       Mm-hmm.

    10. MCMaggie Crowley1:03:58

        And they, they had some templates, their like product review template for FigJam.

    11. LRLenny Rachitsky1:04:04

        Mm-hmm. Mm-hmm.

    12. MCMaggie Crowley1:04:04

        Love that one. Use that one all the time.

    13. LRLenny Rachitsky1:04:06

        Amazing.

    14. MCMaggie Crowley1:04:06

        And so, uh, yeah, I mean this, 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.

    15. LRLenny Rachitsky1:04:18

        Right. Like if they're just like, "Hey, look at this newsletter post letting you write, we should be doing it this way."

    16. MCMaggie Crowley1:04:22

        Mm-hmm.

    17. LRLenny Rachitsky1:04:22

        Versus like, hmm. Like, I think people assume these are the one way to do it or innately will work at your company. And I really like your 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 gonna 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.

    18. MCMaggie Crowley1:04:52

        With... and it can be a little... I think if you don't have the con- that context, it can be a little demoralizing 'cause it's like, "Well, how... like how am I ever gonna do that thing that they, 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," it's more like you can do it in many different ways.

    19. LRLenny Rachitsky1:05:20

        Yeah. And I, 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 gonna be a fit for me? Should I try to implement it?" But still, I think there's an implication, "This is the way to do research. Here's the way to do roadmapping. Here's the way to prioritize." But I think it's interesting that you also yourself create a lot of content and you've... you actually found a lot of value from being a... I don't... let's not call you a content creator 'cause I don't want... I don't like being labeled as a creator myself.

    20. MCMaggie Crowley1:05:54

        Someone once called me a product influencer and I-

    21. LRLenny Rachitsky1:05:57

        (laughs)

    22. MCMaggie Crowley1:05:57

        ... uh, died like a little bit.

    23. LRLenny Rachitsky1:05:59

        That's how I feel. (laughs) Um, 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.

    24. MCMaggie Crowley1:06:11

        Yeah. It's probably the best thing I've ever done for my career, and I am so grateful for the people who, whose idea it was, um, who supported me and, you know, especially at Drift when that, when that became such a part of what we were doing, um, at that time. And it's been helpful for a couple reasons. One is just networking and access. Like, I probably wouldn't be here today if, 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 networkings is the, one of the first benefits. Um, also, you know, building a personal brand is really helpful if you want... E- one of the things that I always wanted to do with my career is try to make it so that...... um, "I'm always employable." You know, I didn't, I just didn't wanna, 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, you know, you wanna 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, 'cause a lot of my job now is, like, bringing people in. And y- 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 wanna work with you," or, "I wanna work on a team like that." And that's huge, 'cause if my job is to hire people, then that's great. Um, and people can get a sense of who I am, um, you know, without needing to be on the phone with me. My favorite benefit, outside of those things, has been that I've le- it's helped me learn more from the work I've done than I otherwise would have been able to. Because in order to make content, you have to think through what you did, you have to summarize it, process it, make it interesting for people, and then, you know, especially if it's in a podcast medium, talk to somebody about it. 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 have if I wasn't, if I didn't have to write something down.

    25. LRLenny Rachitsky1:08:27

        Something that comes across in your content that you've somehow figured out is to avoid it being cringey and very thirsty for followers. And I think when a lot of people hear, "Build a personal brand," it's like, "Ugh, I don't wanna." It's like, yeah, it's-

    26. MCMaggie Crowley1:08:42

        Ugh, I know, I can't ev- it's, like, makes me ill even saying that too.

    27. LRLenny Rachitsky1:08:45

        Yeah. Okay.

    28. MCMaggie Crowley1:08:45

        Like, gross.

    29. LRLenny Rachitsky1:08:46

        I mean, like, I never, I never thought of it or wanted to think of it that way. And I'm just curious what advice you'd give to people that want to go down this route without feeling, I guess, one, just feeling like they're being cringey. And two, avoiding content people will be like, "Oh, my God, I can't believe-"

    30. MCMaggie Crowley1:09:01

        Yeah.

Episode duration: 1:22:33