The Maggie Crowley Hypothesis: Great Product Leaders Excel at Non-Technical Skills

Maggie is the VP and Head of Product for Charlie Health, a startup that provides personalized mental health treatment for teens and young adults. Maggie is also an Olympian and has an MBA from Harvard Business School.

In this episode of the Product Science Podcast, we cover Maggie’s transition from being an Olympic Speed Skater into the world of product. We cover how she entered product, what skills were needed to level up to a product leader, and how to create a product team from scratch.

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Resources

Questions We Explore in This Episode

I think it’s invaluable to find a way to reflect on what you're learning, whether that's through teaching other people, writing, or even a podcast.

How did Maggie’s Olympic journey begin? What Olympic role models did both Holly & Maggie want to be like? How did Maggie go from pursuing ice skating to speed skating? What was Maggie’s favorite memories from the Winter Olympics in 2006? What steps did Maggie take to transition from being an athlete into finding her career path? How did Maggie stumble upon product management during her MBA studies?

What was it like for Maggie at Tripadvisor? How did Maggie learn about product while at Tripadvisor? What was unique about Tripadvisor that allowed Maggie to try out product? What did Maggie learn about product & leadership while at Tripadvisor? What examples does Maggie have of leading through example? How do you learn product at scale?

What was it like for Maggie at Drift? When interviewing, what creates a good fit for a candidate? ****When joining a company, how can you bring your own skills and tools to an already established team? When switching from enterprise to startup, what friction points can one find along the way? How can you show empathy for the work that was done before you join? How is a company’s scale and growth relative to your own professional rate of growth? How do you know when to stay with a company or when it’s holding back your growth to the next level?

When did Maggie start her podcast, “Build”? What did Maggie learn through starting her podcast? How was Maggie able to leverage her podcast to help her grow? After leaving the podcast, are there still benefits to her future growth? How did the podcast help accelerate Maggie’s growth into being a product leader?

How can you transition from being an individual product manager to being a product leader? What tools are there to help reflect on what you’ve learned? How do you present yourself in a senior level meeting? How do you prepare others to accept you as a senior level individual? How do you open yourself up to honest feedback? How can communication and story telling help empower teams and create a shared vision? How do your peers change and what about your communication needs to change with it? Who are your peers before and after you become a product leader? How do you help others in product grow in their own careers? Can you become a product leader by yourself?

What made Maggie want to join Charlie Health? What is the difference between being mission driven and being vision driven? How much did Charlie Health have built without a product and engineering team? How is working in healthcare different from working in tech? What parallels are there between building a mental health program and a good product? How do you build a product team from scratch?

What qualities should a person in product possess? Should a background in engineering be required to enter the world of product? What does it mean to be solutions driven in product? How should criticism be handled? What communication & user research skills are needed in product? How far can a technical background take you in product?

Quotes from this episode

My job right now is to curate and edit what we are going to do and the order in which we're going to do it and those ideas are coming from every part of our company. Click To Tweet To be a product manager, I think you need to have the core characteristics of EQ, empathy, and curiosity. And then everything else, you can figure out. Click To Tweet I think it’s invaluable to find a way to reflect on what you're learning, whether that's through teaching other people, writing, or even a podcast. Click To Tweet

Transcription

Holly:
This week on the Product Science Podcast, I’m excited to share a conversation with Maggie Crowley. Maggie is the VP and head of product for Charlie Health, a startup that provides personalized mental health treatment for teens and young adults. Maggie is also an Olympian and has an MBA from Harvard Business School.

Holly:
Welcome, Maggie.

Maggie Crowley:
Thank you so much for having me. I’m excited to be here.

Holly:
I’m excited to have you. So I always love to start by hearing a little bit about people’s journeys. And normally, I ask for their journey into products but I’m fascinated by your history as an Olympian. I practice an Olympic sport as well, although did not make it to the Olympics because, my God, that’s crazy.

Maggie Crowley:
What’s for it?

Holly:
Figure skating.

Maggie Crowley:
Oh, that’s how I started.

Holly:
Yeah. And so how did you make the transition from figure skating to speed skating, right?

Maggie Crowley:
Yeah. It all started when I was really little, when I was, I don’t know, three or four. All I wanted to do was be Kristi Yamaguchi. So-

Holly:
Oh, yeah, me, too.

Maggie Crowley:
Yep. So saw her on the TV, I was convinced that’s what I was going to do. Convinced my parents to let me learn how to skate. I was living in Maine at the time. And they froze our backyard and I pushed around a little chair. And then my mother is Canadian so we moved to Canada for a while and I was figure skating. And then I saw all these people playing hockey and they look like they were having so much fun. So I switched to playing hockey for a while.

Maggie Crowley:
And then we moved back to the US just outside of Chicago and played hockey but I didn’t have a lot of friends. I was a little bit bored. And my parents, honestly, saw an ad in the paper for a speed skating club and I’d always liked skating. And so they thought, “Hey, why don’t you try that? You’re in middle school, you need more activities to meet people in this new city.” And I just fell in love with it. I loved everything about it. I loved being a sort of individual sport athlete and got really lucky with timing, with coaches, had a good result at the Olympic trials in 2002. And thought, “What if I spent four years, could I actually make the team? Could I really focus? And would it be possible?” And so that’s what I did. And I got lucky enough to make it happen.

Holly:
That’s amazing. Yeah, your time in skating must have been very parallel to my own because I retired from competitive figure skating in 2001. So you went just a little bit longer.

Maggie Crowley:
Yeah, at the time in Canada, it wasn’t a joyous sport. It was very rote. There was a lot of practices that you had to do. It just wasn’t as much fun and I was looking for something that’s more fun. So that’s what got me out of it. But, yeah.

Holly:
Yeah. Cool. Well, congratulations on that.

Maggie Crowley:
Thank you.

Holly:
That must have been an incredible experience to actually go to the Olympics.

Maggie Crowley:
Yeah.

Holly:
So where were they when you [inaudible 00:02:53]?

Maggie Crowley:
They were, 2006, in Turin, Italy. Yeah. I mean, it was unreal. It was a childhood dream, a dream of really anyone of any age. And I’m so lucky and so thankful that my parents could support me and make that possible. Obviously, there’s lots of funny stories about the village and racing and all that kind of stuff. But I think for me, the best experience was being able to walk out … The flag bearer that year was a speed skater. So it was our team that was at the front at the opening ceremony, and being able to walk out in that environment with all the lights and the people screaming, and being right next to the flag was pretty incredible. And I think probably my favorite memory from the whole thing.

Holly:
Cool.

Maggie Crowley:
But then I had to get a real job. So here we are.

Holly:
Exactly, you had to do something other than just that. And I imagine it was a winding journey here as well. How did you get started?

Maggie Crowley:
Yeah, I think like many people who don’t know what they want to do in life, I hadn’t really thought that far beyond being an athlete. And unfortunately, speed skating is not a career where you can make a ton of money. So I went into consulting just because that’s what you do when you don’t know what you want to do and you want to keep your options open and still feel employable.

Maggie Crowley:
So I went into consulting. I did HR consulting for a year. I didn’t love it, switched, moved to New York, like lots of people in their 20s want to do, and worked at like boutique consulting firm that did environmental sustainability consulting, which was really amazing because the group of people were so smart, and so focused, and so mission-driven. And that was my first experience of a company where people were showing up because they cared about the problem they were solving, not just the work and having a job.

Maggie Crowley:
And so that’s something that is relevant for what I’m doing now because I always wanted to get back to a mission-driven environment. But consulting to me was only part of the problem. You only got to see the situation. You got to get a lot of data, interview a lot of people and figure out a proposed solution, but you never got to actually do the work or see it happen or see the result. And I found that to be really unsatisfying because you spend all this time coming up with an idea or figuring out what you should do or a strategy and then you have to walk away. And you never know if anyone is going to do anything about it.

Maggie Crowley:
So for me, I went to business school because I, again, had no idea what I was doing and that seemed like a solid thing to do that would give me a little bit of time to try some stuff out. And a roommate of mine over the summer when I interned at Google, I was just in ad partnerships and he was in product. And he would come home from … We ride the Google bus back to San Francisco together and he would talk about what he was doing and I would sit there saying, “Wait, your job is so much more cool. You’re doing all this cool stuff and what is this role that you’re doing and why do you get to do all this cool consulting stuff but then also come up with ideas.” And he was a product manager.

Maggie Crowley:
And so that was how I found out that it was even a job that was available. Unfortunately, I don’t have an engineering degree so I couldn’t go back to Google as a PM. And the fine folks at TripAdvisor took a chance on me and let me try it out.

Holly:
Oh, cool. So you transitioned over to product after being in ad partnerships and already having your MBA, right?

Maggie Crowley:
Yeah, I was right out of business school.

Holly:
Yeah. So what was your experience at TripAdvisor like?

Maggie Crowley:
It was amazing. I’m so thankful for that experience for a couple of reasons. One, the leadership team, Adam Medros, and Robbie, and some others were so good at what they did, and they were so thoughtful about the processes. And so I got to see what product can look like at scale.

Maggie Crowley:
I was also a part of a rotation program of a handful of other MBAs. It was really special to be able to learn product alongside a group of other people who were in roughly the same position I was in. So I had people to go to to talk about is this how you’re learning, what’s your project like, and I thought that was helpful. And it gave me a way to try out products at a big company for roughly two years. And I learned I wanted to go earlier, I wanted to go to a startup, I wanted to have more ownership and impact. And it was a nice easy way to leave a job without burning any bridges.

Holly:
So how big was TripAdvisor while you were there?

Maggie Crowley:
I could be completely wrong but I want to say it was 3,000 people total.

Holly:
That is large to me. It’s not large compared to like a Google but …

Maggie Crowley:
Right. At Google, I remember the first day of our internship, just walking into a room with a sea of laptops and chairs, and just realizing how big that company was, and how little I mattered. So, yeah, I definitely wanted to go smaller.

Holly:
Yeah. So you mentioned that the leaders at TripAdvisor were really great at what they did. Can you tell me a little more about what made them so great at it?

Maggie Crowley:
Yeah. I mean, they were really good at explaining how to do what they did. And I found they were really great at making sure that we had access to them and that we could see how they worked. I think it trailed off in the later years. But when I joined, we had this really intense product review meeting, where you got to see them thinking about, how do they think about what we should build? What kinds of questions do they ask? How do they interact with one another? What matters to them? And that was something I was really curious about to see, what does product leadership look like?

Maggie Crowley:
And then at the same time, we were all, of course, working on hiring. And I just have a couple of really vivid memories of being in a hiring panel review, thinking about the new people we were going to bring on for the next class for the rotation program, and hearing how they thought about experience and how they thought about interviews and what they looked for. And I just really remember one of them, and I won’t call them out on who it was, but one of them saying, “Is anyone in this room willing to bang on the table and vouch for this person? And is anyone really, really excited?” And it was the first time I heard someone be like, “Don’t settle, hold a really high bar, get excited about the people you want to work with.” It’s stuff like that that’s really stuck with me from that experience.

Holly:
Okay. So where did you go from there?

Maggie Crowley:
Like many stereotypical MBAs, two years of product, I’m sitting there being like, I could do this, I could do this better than you guys are doing this. I want to go be a product leader. So I left and joined a really small restaurant tech startup and I was the second PM and then the other PM left, and I was the only PM. And realized really quickly that when you don’t have anyone around you who’s done what you’re doing, you don’t have anyone to learn from.

Maggie Crowley:
And so I went out on my own and I found myself scouring medium, trying to figure out how people build product teams and how to think about building a product, and even what I should be thinking about because I had seen it at scale but I hadn’t seen it at those early stages. And I just realized that while I don’t think I was doing a bad job, I certainly wasn’t growing as fast as I wanted to grow. I didn’t know what I didn’t know. I was really clear that I was out over my skis.

Maggie Crowley:
At the time, I was in Boston. I wanted to stay in Boston. This was, obviously, pre-COVID and pre-remote work. So I looked around and I found the team at Drift to me seems like the team of the best product people I could find in Boston. We’re doing something interesting, who had a lot of energy that they were scaling really quickly. And it would be the team that I could join, where I would grow with the company and I would have more opportunities as the company got bigger.

Maggie Crowley:
And so I just threw myself at them and at Craig and David and Elias and it was like, “I don’t care what the role is, just let me in, let me learn. And let me come in and learn from you guys.” So, that’s where I went next.

Holly:
Great. And set the stage for us a little bit, where was Drift at at that point in time?

Maggie Crowley:
Yeah, I think I was employee number 82, I want to say. They had just raised a Series B, really great product market fit and it was on that sort of, okay, we’re about to scale this thing like crazy moment, which is, if you can figure it out, is such a fun moment to join a company.

Maggie Crowley:
So I joined and there was maybe three or four PMs there and a VP of product. And we’re just figuring out how we wanted to work. And I was the more experienced PM hire who was supposed to come in and bring some structure, and some bigger company experience. And, yeah, we just figured it out as a team, did a lot of work on how we work, did a lot of work, obviously, shipping features really, really quickly. So I got a lot of reps and sets in, which was really valuable.

Maggie Crowley:
And, yeah, learned a lot about a new space that it was in sales and marketing tech and I had never worked in that area. So it was really interesting to switch into SAS and learn more about how that whole area of tech operates.

Holly:
So what was it like coming in as a person who was meant to bring some structure to an earlier operation?

Maggie Crowley:
All the challenges that you think you would have joining a team that’s already somewhat established, I definitely had. And I remember a little bit of friction with some of the other PMS, who would, if they would listen to this, will laugh about it. And just a little bit of like, what does this person know, what is she going to bring to the team? But as with anything, I think I always view joining a team and whatever skills I have as like, I have a toolkit and some experience and let me see if that will be helpful to you in this moment with whatever challenge that we’re all working on. And if it is, great. If not, cool. I’m going to listen and learn and see how else I can help.

Maggie Crowley:
So that was the attitude I took and I think it worked decently well. I mean, I’m still friends with all of those PMs. I think they’re all amazing and I love them. So, hopefully, it worked out.

Holly:
Awesome. So I guess I want to poke you to be a little bit more direct. You said all the things that you would think, but what are those things? What would you expect?

Maggie Crowley:
For someone joining a team?

Holly:
Yeah.

Maggie Crowley:
I think in particular, my background having an MBA, working in bigger tech company, you’d think someone might be not scrappy enough, they might be too hierarchical, they might want to come in and assert dominance just because of their experience or because of what they’ve done in the past. And there’s just friction anytime you get layered, even if it’s not an actual management layer but someone more senior joins. The team has that question of, “Well, why not me? Why wasn’t I promoted? Why couldn’t I do that job?”

Maggie Crowley:
And I think it’s a really hard thing to do to come in and layer someone or to come in as a more experienced hire. And you have to be really respectful of the work that came before you. And the thing I’ve seen time and time again is when someone like that comes in, there’s this really strong tendency to say things like, “Oh, this product is broken,” or “This is trash,” or “We have to fix everything or it’s all broken,” and you have no empathy or respect for the fact that that’s the team that built that thing and built it to such a scale that you were willing to join the company.

Maggie Crowley:
And so I always think about honoring that work and making sure to respect it and build off of it and help move it forward rather than being negative about it, which I think is a really, really easy pattern for a new person to fall into.

Holly:
Yeah, and I really like how you said honoring that work. I think that’s a really valuable thing to do. So tell me a little more about your journey there. How long were you at Drift?

Maggie Crowley:
Yeah, I was there for almost four years. And it was a wild scaling ride. I did so many things, good and bad, started a podcast, which was terrifying and probably my favorite thing that I did while I was there. I met so many smart people. We built so many products that were good, some that were not good. So really, I feel like I had my coming of age story there because I went in with all these assumptions, knew I needed to grow, and then I grew in ways that I didn’t even know you could grow as a PM.

Maggie Crowley:
So, yeah, I’m having to dig into whichever bucket of experience but I had basically everything you could want in a product role.

Holly:
That’s fantastic to hear. It sounds like that move really worked out for you.

Maggie Crowley:
Yeah. I mean, I think when you join a startup, the promise is that you join and you should be able to scale with the company. And I remember we always talked about when a company goes really fast, your trajectory as a person either can match that growth or you might grow faster than your company, in which case eventually you’ll leave to go do something more challenging, or honestly the company will scale faster than you scale in your role. And then you may also want to leave.

Maggie Crowley:
I remember, David, the CEO, told me that day one. And I sat down … And this comes back to my sporting background, anytime there’s a really big goal, I’m like, “Yeah, I can do that. I’m going to do this. I’m going to be the one that scales with the company.” And so I sat down being like, “All right, I’m going to hang on to this thing and I’m going to grow as fast as I can.” So I went from staff PM to senior director. And that was, again, a pretty aggressive path that I was on. But I really wanted to see what would it take to always be thinking about the next level. What would it take to grow? What would it take to scale that fast? And so that’s the perspective I had going into the experience.

Holly:
So help us understand how much it scaled. When you joined, you said there were three or four other PMS. What was the product like at the time you left?

Maggie Crowley:
At the time I left, the company was well over 500 people, so went from 80 to 520 or [5]30. I don’t remember exactly how many people were on the product team. But I went from being an individual contributor to running one of the … We had three main products, persona-based products. We had a marketer product, a sales product, and an enterprise and admin one.

Maggie Crowley:
So I ran our marketer product and had a couple of group PMs that reported to me and a bunch of PMs that reported to them. So, yeah, I went from IC to manager to manager, managers.

Holly:
So that’s quite a journey in just a little under four years.

Maggie Crowley:
Yeah, it was.

Holly:
So I’m guessing that, in this case, you actually did get some mentorship inside the company and you were able to learn from people around you, in addition to seeking information outside of the company.

Maggie Crowley:
Yeah. So what I tried to do was, of course, I think with anyone, if you’re interested in growth and especially fast growth, I need to be good at the day to day, right? You have to do a good job at your job. You have to ship good products. They have to get out there. They have to be used by people. Obviously, you have to do that.

Maggie Crowley:
And then the other thing I thought about was just being extremely honest with my boss, Craig, who I had on the other progress bunch, just about where I wanted to go. And I had this hypothesis that after having seen people back at TripAdvisor that the work that was being done at the product leadership level was really interesting to me and I thought would better fit the skills that I had. But I knew I had to grind it out as a PM to get access to those jobs.

Maggie Crowley:
And so I was trying to figure out, how do I get through this hard part to the job that I know I’m going to be better at. And there’s a lot of things that are natural to product management that I’m not really super great at and I have to really try really hard at. Whereas the stuff that I’m doing as a product leader, I find to be more natural for me. So I would just spend a lot of time talking to my boss about, “Okay, help me understand what you’re doing. Okay, you did the strategy presentation, can you take 10 minutes and walk me through that? Can I sit in on this meeting? Can I help you with those slides?” Trying to find ways to get into the room to observe and to watch.

Maggie Crowley:
And then the other thing was, honestly, the podcast. And I think it doesn’t make sense for everyone to do a podcast and it’s a ton of work. But that gave me a way to speak to a bunch of people who were in the role that I wanted to be in. And of course, I would have the show and then I would ask them questions, and we would do whatever the topic was. But then when the show would end, I would always steal two, three, five more extra minutes and say, “Okay, off the record, I’m dealing with a situation, what would you do?” Or “How did you do this thing?” And I would get a little bit of extra advice. And I always found that that really helped me level up faster.

Holly:
And how many years into being at Drift did you start the podcast?

Maggie Crowley:
I think it was like a year in. Time makes no sense anymore. So I don’t know exactly when it was, but I think it had to be about a year, maybe a little over a year into being there.

Holly:
Okay.

Maggie Crowley:
Yeah.

Holly:
Because it sounds like that was transformational for you.

Maggie Crowley:
Yes.

Holly:
As a podcast host myself, I completely empathize. It’s so amazing to get to talk to all these people and pick their brains and we learn so much. It’s fantastic.

Maggie Crowley:
Yeah. And I think it wasn’t just that I got the opportunity to speak to those people and build that network. That, of course has been … I didn’t think that that would happen or it wasn’t in my mind when I started the show. But having access to those people and continuing to have access to them is massive. But really, I would say what it forced me to do was to think about what I was doing and what I was learning as I was learning it to come up with good questions.

Maggie Crowley:
So if I was working on a project, I was struggling with something, I had an idea, I had to reflect on it in order to turn it into something I could interview somebody about and not process that forcing function of doing a show every other week for two years, meant that I had to be thinking about what I was learning and writing it down in a lot of ways. And so I was remembering and reflecting and learning better than I ever would have done without that. So even if it’s not a podcast, I would say finding ways to reflect and to write and to learn as you’re going would be my most biggest best recommendation for product.

Holly:
So what do you think is the biggest thing that you recommend somebody do if they’re trying to make that transition like you did from being an individual product manager to being a leader?

Maggie Crowley:
I think the thing that helped me get there was a … I mean, I don’t know if I can boil it down to one thing or two things or a pithy three-part framework. I think at the heart of it, it was like I had this conviction that I could do the job and then I would be good at it. And if I could just get access to it, that then everyone would see that, yes, this is the job for me. So I had that motivation that was internal. It wasn’t external that helped me get there.

Maggie Crowley:
And then I think what I did was, again, finding a way to reflect on what you’re learning, whether that’s through teaching other people, whether that’s the writing, whether that’s through a podcast, I think that was invaluable. I also really spent time making sure that when I showed up in more senior meetings that I showed up in a way that was at the level that I wanted to be at.

Maggie Crowley:
And so example of that is, if you’re going to do some presentation to your leadership or your skip level or something, spend time practicing. I would practice my presentations. I would make sure I was going to think through how the team was going to take in the information that I had. So I was writing and reflecting, I was practicing. And then I was being really honest about my goals and being really curious about what else I could do and always asking for feedback.

Maggie Crowley:
So everyone knew what I wanted. Everyone knew the role I wanted to be in because I wasn’t shy about saying that. And so I would ask for feedback like, “Hey, I think you did a really good job in that presentation, how did you do that?” I remember calling one of the co-founders once after a really bad meeting. And I just asked him, “Look, I’m striking out on this project. I don’t know what I don’t know. Can you walk me through what that felt like for you? Can you tell me what you saw in me in that meeting and help me figure out what I need to do differently?” And I think just asking those questions is really hard and really humbling but it’s what helps you grow.

Holly:
Yeah, that’s really brave to actually ask for a feedback after something has gone poorly. And you’re right, that’s the time when you grow.

Maggie Crowley:
Yeah, there might have been a little bit of muting and then quiet sobbing, and then unmuting and asking further questions. So I’m not going to pretend like I was just hardcore through the whole thing. But, yeah.

Holly:
Yeah, it’s good that they had that culture there where you felt comfortable and safe with the people around you to ask those kinds of questions.

Maggie Crowley:
Yeah. I mean, I wouldn’t say I always felt that way. I would say that’s more about my own life and it’s hard to know. It’s hard to feel that way when you’re super junior or much more junior than somebody, even if they say that it’s a safe space, especially I’m cis white woman, so I’m only one-factor diversity. And I know it can be a hundred times harder for people of other backgrounds to ask that type of question. But at least in that specific day, I had been trying with this project that I knew was going to be a good idea for so long and I just could not break through. And I just got to a point where I was like, “I can’t do another one of those meetings.” So I got to just figure out what I can do to move past this. And that was the only thing I could think of.

Holly:
And are you able to share with us what feedback you got and how it helped?

Maggie Crowley:
I think what I can share is that, first of all, the response was … I think what he said when he picked up the phone was like, “First, I’m so glad you asked this question. This is what’s going to make you grow and make you better is being willing, to your point, to humble yourself and ask for feedback in a really vulnerable moment.” And then he had a really good point how, for this specific project, I had been assuming too much knowledge and I didn’t really tell the story from start to finish on why I thought this was going to be a good investment. And I had assumed that some prior work that had been done was accepted by everybody. And what I should have done is start from scratch and make this argument my own because I inherited this project.

Maggie Crowley:
And so I should have just started from scratch and recreated the argument and made it make sense for the time and the people I was talking to and just simplified it. And it ended up not being that challenging to fix, it was more just making sure I had all the data in a way that made sense and was persuasive for the team I was talking to.

Holly:
Yeah. So one of the things I’m hearing as a theme is communication and presentation skills and the ability to tell a story.

Maggie Crowley:
Yeah.

Holly:
Did you have any particular tools or techniques that you use to learn those skills?

Maggie Crowley:
Yeah. And again, I think the reason why that’s the theme that comes up is that because to me … And this is a very biased point of view to who I am, but I don’t think it’s that hard to build the stuff, right? There’s so much content out there about how to break down the problem, how to move from problem to discovery, how to use the double diamond to narrow in on the right workflow and then how to get it built and building the simplest complete product, all that stuff is out there. And I don’t find that it’s just a matter of doing the work on that end.

Maggie Crowley:
I think the trickier part, specifically to your point about people who want to become product leaders, the hard part is not the building of the thing, the hard part is bringing along the people across the org with your plan and with what you’re building. And so that’s why communication comes up over and over again as an important skill. Because as a product leader, your peers move from being the engineers and the designers that you’re working with, and they become the other functional leaders at the company.

Maggie Crowley:
And so you can’t stick with the comfortable EPD team that you know and love because those aren’t your stakeholders, right? Your stakeholders become your founders. They become ops, sales, marketing. For me now, the clinical team. So I have to think about how am I communicating with them and engaging them, and bringing them along on the journey. And so that’s why storytelling is so important. Because as with anything, the best way to get people bought into what you’re doing is to tell a story, and to hook them emotionally, and to get them to really understand because a really dry metric-based presentation might work for a certain type of person.

Maggie Crowley:
But what executive wants to sit through an hour of metrics, no one really wants to do that. They want to get what you’re doing. They want to have a story. They want pictures. And so thinking a lot about how to do that, I was lucky enough at Drift to work with a guy named Dave Gerhardt in marketing who is unbelievable at this. I’ve never seen anyone who was so good at it. And he followed a really simple framework of situation problem solution evidence like CTA, effectively. It was all from the Presentation Secrets of Steve Jobs, it’s like some book, and a bunch of other marketing books.

Maggie Crowley:
And you just follow that formula over and over again, you get good at it, and you learn how to do it quickly. You learn how to do it persuasively. And then all of a sudden, these things get a lot easier.

Holly:
Yeah. One of the things that struck me as you were talking is how much time, as you’re transitioning to more leadership, you must have spent in conversations and presentations.

Maggie Crowley:
Yeah.

Holly:
A lot of times when I speak to earlier product leaders, they feel like that’s not the work. They feel like, “I want to get back to doing my work.” And I have to talk to them and be like, “No, communication is your work now.”

Maggie Crowley:
Right.

Holly:
Getting buy-in is your work.

Maggie Crowley:
Yeah. It’s funny, you’re totally right. I mean, my situation right now is a little bit different because we’re starting something from the very earliest stages. But when I get to get into a prototype or I get to think about the roadmap, right, get to look at a feature that has launched, that’s the cherry on top and the fun moment. And to your point, that’s not the day to day.

Holly:
Yeah. So you mentioned a couple of hints about what you’re doing. Now, tell us more, you went from Drift to?

Maggie Crowley:
To Charlie Health, yeah. So I bring in all the way back to that second job I had out of undergrad and consulting. What I’ve always wanted to do was to get back to something mission-driven. And just because the culture at that company, like I mentioned, was so powerful and it made your work matter, right? If you’re going to spend so many hours at a company doing something, you want your work to matter. But the challenge of being a consultant is I felt like I didn’t have a trade. I didn’t have a functional role that I could fall back on at an org that wasn’t a consulting firm.

Maggie Crowley:
And so part of my journey into product was trying to figure out what is my trade. What is the thing that I know how to do that makes me valuable as an employee? And again, maybe it’s just me being a little bit conservative and wanting to be employable. But I viewed my time at TripAdvisor and the Drift and other startup I was at as like, let me go out and learn how to do this thing as well as I can so that I can go and do it for a mission-driven company. And so it was always my goal.

Maggie Crowley:
And when I realized I had done my tour at Drift and I was trying to think about what I wanted to do next and I really wanted to do something mission-driven. And I met a bunch of companies and I just didn’t find anything that was really resonating with me. And then I, as a favor to somebody, met these founders who are building this company. And at the time, I didn’t know that they had had any funding. So I was like, “Okay, whatever, I’ll talk to you but this isn’t going to be real.”

Maggie Crowley:
And they were building this amazing program and product to help high acuity teens and young adults get the help that they needed. It’s a really underserved market. There’s not a lot of high acuity care for young people. So that’s things like people who have just been hospitalized for suicide attempts, who have substance use disorder, other depression and anxiety.

Maggie Crowley:
So the idea that you could help kids at that age, learn the skills that are going to serve them through the rest of their lives, and deal with really, really serious issues, it was amazing. And then I had a moment where the CEO said, “Our goal is to reduce teen suicide rates in this country.” And I was like, “Great, sign me up.” I’m not going to find anything else that’s motivating to me and being able to see the direct impact of the work that we’re doing on specific human beings is beyond anything.

Maggie Crowley:
So, yeah, I got hooked by the mission but the interesting part is that this company, they had built everything without product engineering and design. And so it was a rare opportunity to come in and build a product team, engineering design team from scratch while knowing that we already had business model validation, which is interesting and rare opportunity and something that I had never done before and I was really, really excited to do.

Holly:
Yeah. So how did they build it all without a product and engineering team?

Maggie Crowley:
What’s interesting about building in health care is that it’s really common to build with tools. The default is not let’s get the devs on this. The default is like, “Okay, what tool can we use that solves this problem?” And so a lot of healthcare companies, as I’m learning, healthcare tech companies are a really tangly amalgamation of third-party tools, and people, and processes.

Maggie Crowley:
Again, I’m not going to speak as if I know a lot about health care, I’m very new, I’ve only been here for three months. I’m still beginner mind. But that’s what they focused on creating the best curriculum and figuring out how to create a virtual intensive outpatient program that drove results. And they didn’t waste time building something until they knew they really needed to.

Holly:
Do you see any parallels between how they developed their mental health program and how a good product is developed?

Maggie Crowley:
Yes. So I think what’s really interesting is that you could think about the situation that I walked into as start from scratch whitespace, you get to do whatever you want. But I saw it as we had a year and a half of really incredible organically created user research. And it was this really rich set of workflows and processes that the team had created over time to help solve problems.

Maggie Crowley:
And so it’s almost like a team doing human-centered design on themselves without knowing that that’s what they were doing. And so you can look at all the ways that they do the things that they do as little research projects.

Maggie Crowley:
And so the interesting thing from a product and design standpoint is, how do you take that and figure out what is core to this experience and what is just a workflow that has been created because they couldn’t figure out how else to do it or there wasn’t another workaround for whatever tool. And I think that’s common in all product development, which is observing your users and trying to figure out which workflow is the signal that you want to build on versus which workflow is a gross workaround that you should get rid of.

Maggie Crowley:
And so that’s really interesting to me is thinking through, what do you want to keep, what do you not want to keep, and how do you think about those workflows.

Holly:
So how do you figure that out?

Maggie Crowley:
Great question. Let’s talk in a year. And this is going back to the threat of product leadership and I think an interesting question that I’ve been asking myself or series of questions now that I am running the team. And what’s interesting is, you walk into a situation like this and you can say, “Okay, if you had to do it yourself completely from scratch, what would you do? What would you keep? What are your principles? What would you do differently? All the way from like, would you use Jira to how do you think about goals? How do you think about product principles? What are your tenants as a team? Who do you hire? What’s your org chart?” But you have to ask all of those questions of yourself.

Maggie Crowley:
So for me, the way that I make sense of that sprawling, super stressful set of questions … Because it can be overwhelming, right, if you just sat down and you had to just do all of that at once. The way I always think is, “Okay, what is the business goal? What are we here to do?” Really try to understand that, get a sense of the market, your competitors, where you’re at, all the context of the business. Then look at where is it right now, really understand what’s currently happening, the ground truth, and then look at both those sets of information and find the gaps. Find the gaps, find the big gaps, and then just start with the biggest worst gap, and then you can figure it out over time.

Maggie Crowley:
And so that’s my approach is, if I understand where we’re trying to go and when, if I know where we are, it almost always becomes pretty clear what you need to do to get there. And so I think that if you’re rigorous about using that framework, you can reduce the amount of decisions you have to make and allow yourself to focus on what really matters.

Holly:
Cool. All right. So you’re three months in and the company is almost two years old or so. So how many people work there now?

Maggie Crowley:
I think we’re just over a hundred.

Holly:
Oh, pretty big for that age.

Maggie Crowley:
Yeah. But we’re a provider so we employ our clinicians full time.

Holly:
Got it. Yeah. So the actual product and tech team is probably tiny.

Maggie Crowley:
There’s three of us.

Holly:
Yeah. That is an exciting days to be at and to see the amount of user research that was organically done for just the purposes of them getting the program started that you get to then dive in and use must be exciting.

Maggie Crowley:
Yeah, it’s really interesting and it’s really fulfilling, I think, for me to go back through all of the things that I’ve learned over the past, I don’t know however many years, and think about, “Okay, what have I done in this situation?” Which thing is going to help me? And then where do I have just massive gaps because I’ve never thought about a problem in a certain way.

Maggie Crowley:
So I think going back to the podcast and the network, having built up a network of people that I can ask questions to is probably another thing that I would recommend to people who are thinking about a leadership role or who have recently moved into one. You can’t do it all yourself. You have to have a group of trusted advisors or groups of trusted advisors that you can reach out to. And so I have a couple of small, tiny, three-person Slack workspaces. I have a couple of people that I can text. And those are the people that I go to when I have some thorny leadership question that I know have perspective.

Maggie Crowley:
And so building that network has been something that I didn’t really realize I was doing intentionally, but now I realize has allowed me to do a lot of the things that I do faster.

Holly:
Yeah. And I think that some people unintentionally build a network but not everybody actually continues to pay that network and ask them questions and use them as a resource. So that’s also a skill.

Maggie Crowley:
Yeah. And I’m super introverted, I don’t love doing it, I find it to be really difficult. But at the same time, I’ve been really surprised over time at how generous people are with their time and how willing they are to answer questions. And people have worked really hard to build up the skills that they have and to go through the experiences that they’ve gone through. And I find that they’re often happy to tell you about it because they’re proud of the work that they did and they want to share it. Or on the flip side, they went through something super painful and they would love to help other people avoid making that same mistake that they made.

Maggie Crowley:
And so, every time I ask a question like that, I’m, of course, appreciative of the answer but then I also try to pay it forward. And when people ask me questions, if they ever do, I try really hard to answer them if I can because there’s no sense in hoarding the knowledge for yourself. That doesn’t help anybody. And I think hopefully my whole perspective has been the more I can share about my journey and what I’m learning, the easier it makes it for somebody else to do this, too.

Holly:
Cool. I like that. It’s like your own mission as well.

Maggie Crowley:
Yeah. I mean, I think products in general, and maybe you touched on this in other episodes with other guests, but it’s just one of those roles that for reasons that are silly is really hard to get into. And it’s hard to get someone to give you that first stamp as a product manager. And it’s for no good reason. It’s a really hard job and I think requires a certain set of skills, but I would love to open up access to it to more people from more backgrounds. And I try really hard to pull people up with me and not shut doors.

Holly:
So what are the qualities that you look for when you’re either hiring or maybe thinking about helping somebody out? What do you see that says, “Okay, this is a person who’s going to be a great product person?”

Maggie Crowley:
Yeah. These are probably all cliche answers, but I look for people who were curious about getting to the right answer and who are not worried about having the right answer. I’ve definitely worked with people who need to be right and need to be the idea person. And that gets in the way of progress, I think. So intellectual curiosity, people who are resilient in the face of criticism or critique. So again, people who can move forward, who can recognize when things are going bad and are not overwhelmed by that and who have a little bit of like, “Okay, cool, yeah, that didn’t go well, let’s talk about it.”

Maggie Crowley:
Storytelling and communication, empathy, EQ are all critical product skills, I think. And then everything else, you can figure out. I don’t think everyone has to be perfectly analytical. Not everyone is going to be amazing at user research. Not everyone is going to be amazing at designing products. So I don’t have a strong point of view on what you have to be able to do, but I think you need to have those core characteristics of EQ and empathy, and curiosity.

Holly:
Yeah, which are characteristics that are great for leadership of any kind, right? It’s interesting that you aren’t saying a lot about the technical side. And I think you alluded to maybe some challenges getting into products without having an engineering background. What has that been like for you?

Maggie Crowley:
Yeah, I have a hard line on this. I think it’s so silly to require that stuff. It has no bearing on whether someone is good at identifying problems and motivating teams to solve them. I think in some specific instances, specific experience would make you a better PM at a specific product. If your product is really technical and you have a background in whatever field.

Maggie Crowley:
I have a friend who just started a company and it’s doing something crazy with machine learning that I can’t explain to you because I just purely don’t understand it. But she doesn’t have that background and she spent a lot of time reading papers and working with doctors to figure out the space. And, yeah, maybe for her, it would be easier and make more sense if she had a master’s degree in data science.

Maggie Crowley:
So that’s the thing where you still don’t need to have it, it might make your life easier if you do. But I think the basic requirements, you don’t need those things, you can learn them on the job. And I also think that I’m glad you call them technical skills and not hard skills because I find that the “soft skills” are 10 times harder to learn to coach And to get good at than, did you do the analysis right? Because usually, yeah, that’s a yes or no question, right? You can say, “Yeah, I did it right or I didn’t.” But did you suss out the feelings of your team? Could you figure out how to frame the problem in a way that motivated the engineers to solve it even if it’s like a boring billing problem?

Maggie Crowley:
Have you created a roadmap that you can get your founders to buy in on? That’s hard, that’s hard stuff. The technical things are much simpler in comparison, in my opinion.

Holly:
I love what you said there. I feel pretty similarly. I don’t believe engineering degrees are needed to be a product manager at all. I think some of the greatest product managers come from other fields. And there’s so many different skills that go into being a great product manager.

Maggie Crowley:
Yeah.

Holly:
And you’re right. Some of them are easier to teach than others.

Maggie Crowley:
Yeah. It’s also like how arrogant to think that I need an engineering degree when I’m working with amazing engineers. My job isn’t to be an engineer. My job is to figure out what do we need to build to move our business forward. That’s my job. The head of engineering, it’s their job to figure out the technical approach.

Maggie Crowley:
So I think it’s just a really weird thing to say that you have to be an expert in all of those things because you don’t. And then, to me, it’s like, you should focus more on how do you hire and trust and build a trusting relationship with your design and engineering leaders rather than thinking that you have to be able to do all of it.

Holly:
Absolutely. Do you have any other areas that we didn’t touch on that you’re passionate about?

Maggie Crowley:
So what’s interesting about the job I’m in right now is that most of the people I work with have never worked with people in product management. So there’s a lot of stereotypical educating the team while you’re also doing the work. And it’s been amazing because the team is so excited and they love it. And they think it’s interesting, which is really cool. And there’s a little bit of that, wow, that’s magic, which I think is really fun. And, usually, something that I feel like engineers get more than PMs get so it’s cool to have a little bit of that.

Maggie Crowley:
But I’m thinking a lot about how to explain what it is to people. And I’ve been talking about it as editing and curation. So I’m not sitting here coming up with weird ideas in a vacuum. My job right now is to curate and edit what we are going to do and the order in which we’re going to do it. And those ideas are coming from every part of our company, from our clinicians, our admins, analysts, associates, ops. Every team has good ideas on what we should be doing and when and why.

Maggie Crowley:
And so my job right now is much more like a curator and editor. And I’ve just been thinking about that a lot as a way to think about the product leadership roles less follow my perfect vision into the future and more how do I curate and edit a vision that works for everybody.

Holly:
Cool. I really like that. I think the best leaders are people who really see their job as making sense of and amplifying what’s coming from everybody else.

Maggie Crowley:
Yeah. I love that word, amplifying. I think that’s exactly right. And, yeah, just thinking about what values do we want to have and who are we as a team. And it’s a really cool opportunity if people who are listening to this ever get a chance to start a team from scratch. I’m not sure I’ll ever do it again. It’s really hard. But it’s been really cool and really fulfilling to ask those questions.

Holly:
All right. Well, where can people find you if they want to learn more?

Maggie Crowley:
Well, they can find me on Twitter. That’s where I am the most @maggiecrowley. I love talking about products. I love getting into conversations about the best way to do things. My DMs are always open. So if people have questions, they can find me there.

Holly:
Awesome. All right. Well, thank you so much, Maggie. It’s been a pleasure to talk to you today.

Maggie Crowley:
Yeah, Holly, thanks for having me. It’s really fun to be on the other side of these conversations.

Holly:
Yes. Yes, it is.

Maggie Crowley:
Yes, a lot less work, I will admit.