Skip to content
Lenny's PodcastLenny's Podcast

Deb Liu: How to PM your career like a product you ship

How to write a spec for your career: vision, metrics, milestones; introverts learn self-promotion as educating others, the way Deb built Marketplace.

Lenny RachitskyhostDeb Liuguest
Aug 22, 20241h 11mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 2:18

    Introduction to Deb Liu

    1. LR

      You're VP of Product at Facebook. You're a director at eBay and PayPal. You're on the board of Intuit. You've been the CEO of Ancestry now for the past three and a half years. This is a career path that a lot of people dream of.

    2. DL

      You know, some of the best PMs I have ever worked with are terrible PMs in their careers. They just drift from job to job. "Hey, should I take this role or this role?" Like, "How do I think about this?" But if I said you had to write a spec for your career, what does success look like? How are you gonna get there?

    3. LR

      You wrote this awesome post about introverts and how hard it is to be successful as an introvert.

    4. DL

      The workplace is really favoring people who can speak up. It looks like self-promotion. "I wouldn't want to do that," because it's self-promotion. But instead, what if I called it educating about all the great work your team has been doing, helping people see why your team should get more resources? You have to actually share what you do.

    5. LR

      Is there something that you believe that you think most other people don't believe?

    6. DL

      The most important career decision you make is who you marry. Is this person lifting you up or pushing you back? You will have a much more successful career if your home life is in balance. It's like a yin and a yang.

    7. LR

      (instrumental music) Today, my guest is Deb Liu. Deb was VP of Product at Facebook, where she spent over 11 years, and while there, created and led Facebook Marketplace, which is now used by over one billion people monthly. She also led the development of Facebook's first mobile ad product for apps and its mobile ad network, also built the company's games business and payments platform, including Facebook Pay. Prior to Facebook, she was director at both PayPal and eBay. She's on the board of Intuit, and for the past three and a half years, she's been the CEO of Ancestry. I actually generally have a rule of no CEOs on this podcast, but to me, Deb is a great exception because she is a product person at heart. In our conversation, Deb shares a ton of tactical career advice, including why resilience is so key to career success, how to PM your career like you PM your product, how to be successful in business as an introvert, what she's learned about building multiple billion-dollar zero-to-one businesses within a large company like Facebook, and so much more. Deb is so full of wisdom, and I'm really excited to share her insights with more people. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes and helps the podcast tremendously. With that, I bring you Deb Liu.

  2. 2:18 – 9:45

    Deb’s career journey and key advice

    1. LR

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

    2. DL

      It's wonderful to be here, Lenny.

    3. LR

      It's wonderful to have you here. You have had such an incredible career. You're VP of Product at Facebook. You're a director at eBay and PayPal. You're on the board of Intuit. You've been the CEO of Ancestry now for the past three and a half years. This is a career path that a lot of people dream of, and honestly, just, like, one of those roles is a dream for a lot of people. And so, I wanted to start with just, uh, this question, and I wanna see where the conversation takes us. If you could give one specific piece of advice to someone that's looking to do well in their career or to do better in their career based on what has worked well for you, what would that be?

    4. DL

      Always be learning. And I tell this to everybody. So I often tell people, "Someone who's always learning is always gonna exceed someone who's the expert today." You're gonna find people... You know, the one thing about school is that we go to school, and there's such a thing as getting 100 on the test, a perfect score on the SAT, graduating with a 4.0. Well, there's nothing like that in careers, right? We think... It's actually a nonlinear experience, and there's always someone better than you at speaking or presenting or strategy or execution. But if you're always learning, learning from the best, getting feedback, you're always gonna get better every single day. And that's what I have always held, which is, each job I took, I didn't necessarily qualify for it. I wasn't necessarily the very best at it. And so I became a student of being better at that job. And once I mastered that, I was a student for something else and something else and something else. And so I always balanced learning and impact, which was, you can have the most impact at the job you know the best, but then you stop learning. And if you're learning all the time, you're not necessarily having impact. So how do you keep going back and forth and back and forth so that you're not going straight up a ladder? You're actually laddering back and forth into different things where you're having an amazing time, where you know everything, and then you're the newbie again and learning new things. And you're incorporating what you used to know into what you're learning and the impact that you have today and so on and so forth.

    5. LR

      This episode is brought to you by Pendo, the only all-in-one product experience platform for any type of application. Tired of bouncing around multiple tools to uncover what's really happening inside your product? With all the tools you need in one simple-to-use platform, Pendo makes it easy to answer critical questions about how users are engaging with your product, and then turn those insights into action. Also, you can get your users to do what you actually want them to do. First, Pendo is built around product analytics, seeing what your users are actually doing in your apps so that you can optimize their experience. Next, Pendo lets you deploy in-app guides that lead users through the actions that matter most. Then, Pendo integrates user feedback so that you can capture and analyze what people actually want. And the new thing in Pendo, session replays, a very cool way to visualize user sessions. I am not surprised at all that over 10,000 companies use it today. Visit pendo.io/lenny to create your free Pendo account today and start building better experiences across every corner of your product. P.S. You want to take your product-led know-how a step further? Check out Pendo's lineup of free certification courses led by top product experts and designed to help you grow and advance in your career. Learn more and experience the power of the Pendo platform today at pendo.io/lenny. (instrumental music) Pendo. This episode is brought to you by WorkOS. If you're building a SaaS app, at some point, your customers will start asking for enterprise features like SAML authentication and SCIM provisioning. That's where WorkOS comes in, making it fast and painless to add enterprise features to your app,Their APIs are easy to understand so that you can ship quickly and get back to building other features. Today, hundreds of companies are already powered by WorkOS, including ones you probably know, like Vercel, Webflow, and Loom. WorkOS also recently acquired Warrant, the fine-grained authorization service. Warrant's product is based on a groundbreaking authorization system called Zanzibar, which was originally designed for Google to power Google Docs and YouTube. This enables fast authorization checks at enormous scale while maintaining a flexible model that can be adapted to even the most complex use cases. If you're currently looking to build role-based access control or other enterprise features like single sign-on, SCIM, or user management, you should consider WorkOS. It's a drop-in replacement for Auth0 and supports up to one million monthly active users for free. Check it out at workos.com to learn more. That's workos.com. You talked about, like, you got into a new job maybe you weren't ready for and you, like, had to learn on the job. So either maybe share a story of one of those experiences, or just, like, how do you actually do this? So if someone's listening, they're like, "What? How do I learn? What am I learning?"

    6. DL

      Well, I'll start with my career in tech. So I had, um, I had worked in consulting before business school. I went to Stanford for business school. I came out to California. Didn't know that much about tech. But I really loved using eBay, so I interned there my fresh- my first year in, um, business school. And then when it came to finding a job, I really wasn't sure what we wanted to do, but we wanted to move back to the, the East Coast. And so I went out looking and couldn't find a job. Like, it was really hard. It was 2002. And so I kind of ran into Tim Wentzel and Catherine Wu. So they... Catherine Wu is from Airbnb, as you might know her. And, uh, Tim Wentzel put together the PayPal mafia. He was the recruiter for PayPal. Went to this table and I said, "Absolutely love PayPal, use it all the time. I'm a big seller on eBay." And he's like, "Do you want a job?" I'm like, "No, I'm actually going back East." And he's like, "Just come in and talk to us." And so I said, "Okay, well, what kind of jobs do you have?" And he's like, "I have jobs in product and I have jobs in marketing." Now, I had taken a marketing class, obviously, in business school, and I said, "I wonder what this other product job is." So I look over at Catherine, and I had kind of seen her around Stanford before, so she, uh, she was a year ahead of me, and I said, "Well, what do you do?" She said, "Product." I'm like, "That sounds good. I'll do that." And that's actually how I fell into product management. Well, I w- actually, and I'm embarrassed to say, faked my way through those interviews. Because during the interviews, they're like, "Well, what would you build?" And since I was an avid user of both products, I could really richly say, "Here are the, here's the product feedou- feedback I have. Here are the new products you should build. Here's my feedback on things that we should be doing differently." And they said, "Congratulations," and they gave me the job. And embarrassingly, I went to the first day of work and I said to Amy Klemet, who was the VP of product at the time, and I said, "Okay, I literally have no idea what this product job is." And she showed me the ropes and she was so incredible. She actually showed me. She said, "You know, all those ideas you had, all that energy you had around building these things. We go do that. Let's go do it." And I said, "Well, how do you do that?" And she said, "Well, you write down what you want to build and then you work with the engineers to do it." And I just remember thinking, "This is crazy. I have no idea what I'm doing." And it was such an incredible adventure, though. Those first few years, I just learned so much about the craft of building. How to really think through product use cases, how to think through what customers wanted. Not just a customer of one, myself, but really what true customers and customer cohorts wanted. And so it was really a time when I felt like I was really blossoming. But I didn't come in with mastery. I came with a curiosity. And I think that's what made me a great product manager, was that I didn't have a set way of doing things. There wasn't some playbook I was trying to play. There wasn't some framework. But instead, I was willing

  3. 9:45 – 11:27

    Navigating new roles and challenges

    1. DL

      to learn.

    2. LR

      So one takeaway might be from this l- uh, the phrase "Fake it 'till you make it." Uh, any thoughts on just how to... Like, I imagine many people right now are like, "Oh, I'm trying to get a job as a PM. How do I do this? That sounds great. I'm gonna pass this interview, figure out the job as I, after I join."

    3. DL

      Coming in with humbleness was really important.

    4. LR

      Mm-hmm.

    5. DL

      But during the interview process, actually, I didn't realize this, but they asked me questions as if I was a product manager, as if I knew what I was doing. And I think when you have passion around a product or passion around a company or around a business model or around something, it shows. And so it's not necessarily faking the enthusiasm-

    6. LR

      Yeah.

    7. DL

      ...or faking the idea that you want to work there. But, you know, you don't have to know how to write the spec or PRD or briefings or anything like that. You don't know how to d- have t- know how to do customer research or da- do data analytics or read, read, you know, read reports. But instead, show your passion around the product itself, around the use case, around the customer. Show who you are and why you care. I think sometimes people just say, "Well, I want a product job." But, you know, you have to be able to fall in love with the problem. You have to fall in love, not with the product, but I said the problem, right? The use case. What problem are you trying to solve? And if you can do that, you can be a great product manager even without a lot of experience.

    8. LR

      That's an awesome piece of advice, so just, like, lean into the passion. One... First of all, part of it is you have to be excited about the thing you're trying to work on or thinking about the company you're thinking about joining. Sounds like that's a prerequisite here. Uh, I ha- we have a podcast episode with, uh, Uri Levine, who has a whole book called Fall In Love With The Problem, which is all about that same idea, actually, for startup founders.

    9. DL

      I'll have to read it.

    10. LR

      Yeah. He has a, he has... He always wears a shirt, "Fall in love with the problem, not the solution."

    11. DL

      Yes.

    12. LR

      (laughs)

    13. DL

      Yes. That is absolutely the most important skill for a product leader.

  4. 11:27 – 15:07

    Overcoming adversity and failure

    1. DL

    2. LR

      Something else I've heard you talk about in terms of s- something that contributed to your success is, is, uh, being okay with failure and just bouncing back quickly versus avoiding failure. Is that something that you come back to a lot?

    3. DL

      Well, here's what I notice about everybody in... You know, I have coached a ton of people in my life. I have managed big teams. And, you know, the people who are most successful are not the people who had no failures, whose, who would live charmed lives and head up into the right careers and got promoted every cycle. The people who were most successful were the ones who actually, through adversity, learned to turn stumbling blocks into stepping stones.They were the ones who got hard feedback and then came back stronger, because now they learned what to do differently. They're the ones whose products failed, but they said, "You know what? I'm gonna turn this failure into success. I'm gonna take those lessons and make this company stronger." The ones who, you know, when you live a charmed product life, you always work on everything that's easy. You don't, actually, you know, trees are strong because they bend in the wind, because they're tested, because it's cold, because it's windy, because there's conditions, and that's how a tree goes, grows strong and suc-, and you know, tall over many generations. And I think sometimes we think, "Oh yeah, you know, I wish I lived a charmed life," and that is not what we want. You want to have enough adversity that you learn to overcome so that you can build stronger over time and build resilience in your career. And I've seen that so much, which is the best product leaders I've ever worked with are the ones that have the toughest stories, that had the hardest feedback, but also the ones who were able to bounce back quickly and make it happen.

    4. LR

      We have a segment on this podcast called Failure Corner where people share a failure they went through, kind of along the same lines, and something they learned from that experience. Is there an example of that from your career where a failure made you stronger?

    5. DL

      Yeah. I remember, um, there was a job that I really wanted at Facebook, and I'd been there for a long time. I had been, you know, leading different teams. I was a VP of product and then GM, and there was a job, there was one job that I never got to do. So I got to do all the jobs I wanted and Mark gave it to someone else. And I told him at the time, when he gave it to the first person, who was amazing at it, I said, "You know, if this job were open, I'd like to be considered for it." The job opened up later, gave it to someone else, and I said to Mark again, like, "I really wanted that job." And he said, "Not only will I not give you that job, you know, I'll ne- you'll never have that job at this company."

    6. LR

      (laughs) What?

    7. DL

      And he didn't say it harshly, he didn't say it... But he was giving me feedback about something which, he did not see me in that role, in a role that I really wanted. And I had to decide each time, like, "What do I do with this information?" Right? This is a, my dream job. I actually, I decided I was gonna turn the job I had into the job I wanted. And that's a choice, right? I could have said, "You know what? I can't have that job. I could go do someplace, something else." But I didn't. I took the job I had with the team I had and I turned it into a thing that was gonna be something we wanted. And so I think sometimes it's not... You know, I think that that experience was a very humbling experience, because, you know, to be told no and then to say that this will never happen was really hard. But at the same time, it was a reminder that you're not right for every job, even if you think you are.

    8. LR

      Yeah.

    9. DL

      And that you can take the raw materials of what you have and turn it into what you want.

    10. LR

      Are you able to share what those jobs were that you wanted to get that you never got?

    11. DL

      I never actually shared it, uh, publicly, but it's something which... You know, I had always had a role that, where I, I did new things for the company, and there was a role where it was running something which, you know, more of an existing business, but I had always been kind of the innovator, the new, the new stuff person, right? I had taken over so many new things. And so, you know, maybe that wasn't the right thing at the right time for me. But it was something that was really incredible and a turning point

  5. 15:07 – 19:33

    Building billion-dollar businesses at Facebook

    1. DL

      for me.

    2. LR

      A great segue to an area I wanted to spend some time on, which is building zero to one stuff within a larger company. So from what I can tell, you built two billion-dollar businesses within a large company, Facebook Marketplace, and then the ads platform within Facebook, and maybe more. I don't know. Uh, the payments stuff? The games? I don't know. Maybe there's billions of dollars there I don't even know about.

    3. DL

      (laughs)

    4. LR

      And this is very rare and very hard. And it's something we talk a little bit on this podcast, just the skills to build something new. And I know with Marketplace, it was not something people believed in for a long time. It took a lot of work to convince people to actually give it a shot. So, I guess the question here is just, what have you found are key tactics to start something new and allow it to continue to exist and get to a place where people start to believe it? What, what has worked for you?

    5. DL

      So first, I didn't build the ads platform.

    6. LR

      Hmm.

    7. DL

      I actually built the first direct response ad product-

    8. LR

      Hmm.

    9. DL

      ... the company ever had. Um, but w- we'll talk about how that led to, uh, why direct response is a vast majority of the ads, um, revenue for the company. But one thing that it was really interesting is that I just, you know, I really saw my opportunity at Facebook to be somebody that zigged when other people zagged. Like, there were amazing people who did a lot of the really core products, right? Working on feed, photos, like, videos. And I, you know, I came in actually on the payments team, and we worked on payments and eventually built Games, which was the first billion-dollar business. It was very successful. Uh, we worked with the likes of all the game companies that were on kind of the Canvas Games platform. And it was just an incredible opportunity to start from scratch and build something really cool. We built Facebook Credits, which eventually, um, became kind of the Fa- face of payment system. And, you know, then from there on, I built the first direct response ads product and again leveraging the skills that we had. We had a lot of relationships with game companies because of my time in payments, and so we just said, "Hey, look, what ad product do you want?" And they said, "Actually, our biggest challenge, like your biggest challenge, is the shift to mobile. Build us a mobile acquisition engine." And we said, "That's doable." And at the time, the company was very brand-oriented. Most of the ads on the... Actually, almost all of the ads on the platform were brand, and we were not even on the ads team, so we actually worked on this team called the platform team. And we said, "Okay, we'll build an ads product for the Facebook feed, the new mobile Facebook feed," and suddenly became a billion-dollar business within about 18 months, which was such an incredible journey. Um, we worked on the, um, adverti- the mobile advertising platform, so basically a mobile ads, um, network. That was a, a great experience. And so each time I worked on something, it was just... I, the thing that you have to remember is the failure rate for something like this is very high. You know, you start something and the amount of iteration. People think, "Oh yeah, it's very easy." You start something and it's linear 'cause you have all the resources of this company behind you. But actually, everything in a company is like, "Let's do the most important thing. These are kind of seeds and we'll just let them..." And so if you do that, you have to know that you don't get a lot of resources, you don't get a lot of attention. And I appreciated that because I think I work best when people aren't... There is not a lot of scrutiny.I think sometimes large companies, they say, "Well, this innovation team..." and then they check in on them way too much to like week-to-week progress. "Where are you going? What's your strategy?" But so much as you know, it of, of building something new is the iteration process. It's the failing a lot. We actually tested fif- like five or six versions of the ads product before we got, got it to take off, and it took months. And then, eh, we were on the verge of death multiple times. In fact, I actually went back to run the payments team while I was working on that product because the team we had gathered still wanted to continue working on it. But I needed a second job back on the payments team (laughs) because they asked me like this, "We don't think this thing is gonna work. You should go run your old team again." And I thought, "Well, I will do both." And so I did both for a while until it really took off. And I think the, the thing that I think a lot of large companies don't realize is that you can love something to death, right? (laughs) And say with every new product, I'd rather kind of do it out of the limelight, do it with some li- minimal resources, and then have the freedom to fail. Because success and failure really is, you know, the in startups failing, failing fast is really important or succeeding fast, right? It's the long slog that makes it really hard. And in a company, you end up getting cut if you're the long slog product. And so being able to just say, "You know what? We're pruning this. We're doing the next thing and the next thing." And then having the time to iterate and grow is really critical.

  6. 19:33 – 23:40

    Strategies for zero-to-one innovation

    1. DL

    2. LR

      So as a leader trying to do this, and it'll create space for this, is there something you've learned about how to allow for, "Don't over scrutinize this. Don't look at us too carefully. Uh, we don't wanna be in the limelight. Don't put too many resources on this yet." Is it just like, "Hey Mark, here's what I think." I imagine it's not as easy as that. There's like a lot of-

    3. DL

      (laughs)

    4. LR

      ... you know, uh, influence and that kind of work. Is there anything, any tactics there you could share to create this sort of environment?

    5. DL

      I think the most important part of the environment is really patience. Patience with, and you know, again, this is a portfolio strategy, and I tell every PM who, you know, I used to do a new hire PM class, and I said, "Look, a lot of you are going to go into the core product, and your job is to grow X by 3% to 5% every six months, right?" Like growing, you know, engagement or growing sessions or maybe growing video views or whatever your metric is. You're trying to grow something 5% and then, you know, you, you, you exceed expectations. And I said, "And then a bunch of you are like, 'I wanna do something new. I'm gonna build something from scratch.'" And I said, "By the way, a very, very successful company for a new set of products has a 50% hit rate. So if half of you are gonna come back in a year and have a different job because that did not work out, do you have the resilience to do that?" And I think somebody, you know, you enter a large company, you're eas- by the way, you can have an amazing career building core products. Like that is a incredible journey within, 'cause you learn so much about the mechanics of what that takes. And yet at the same time, I found a lot of energy from doing something that someone hasn't done before. And so I really enjoyed the, "Hey, this thing could fail. Let's pivot. Let's try to figure out, let's prune this, let's try that." And, you know, not everything ha- I did there succeeded, but you know, a lot of the things that are lasting, the lasting products are ones that gotten really big. And so for me it was a greater reward and it, it made the journey so much more interesting. But for others, I think, you know, work on the core product, learn the skills. It is absolutely respectable as well. But if you choose to be the person who works on innovation, new products, expect in a year, you might literally have nothing to show for it but the lessons that you learned. And I think those lessons are really precious and we often underestimate that too.

    6. LR

      Along those lines, do you think it's a good career move to do a Zero To One thing within a bigger company? Or is it often a bad idea? Do you have any advice there for folks?

    7. DL

      It depends. It depends on your personality in the company. So the one thing I realized about, about my role was that I did a lot of... I, I had like five different careers at the company over 11 years, you know? And so most people don't realize that when you work on new things, you're constantly adding to your portfolio, subtracting from it, growing things, pruning them. And so you could just work on so many cool things except, you know, you're, you're the... everything has similar kind of, it's like it rhymes, but it's not exactly the same, right? So you learn the lessons of how to get things done, how to get resourced, how to get support when the product's not working, how to, you know, not get pruned in the next culling. And those are really, really important skills. But I think for people who are just starting out their career, it is a very high risk thing to do. So if you're very early in the career, I encourage people just learn the core skills first. You can learn the core skills when there's a lot of stability. This product is growing, you know, X percent, like 5%, and you're gonna grow at 10. That's amazing. Like that is because you are there, you're gonna change the trajectory of the product. Or this thing is, you know, this thing has 100... uh, you know, 100,000 users, you're gonna get it to 200,000. Like that, those are the kinds of things that are, you know, going to be successful for you and you can put on your resume. But I think it reaches a point in your career where you have to decide, when am I gonna take the big swing?

    8. LR

      Mm-hmm.

    9. DL

      Because the big swings are the things that you can, you know, you write your career stories about. They're not just, I moved this metric X, but I changed your trajectory in this way. And so the big swings though have a lot of failures along the way. And so you have to understand you're, you're making trade-offs in that. And I encourage everybody to take some time, two, three years in their career when they're ready for the big swing. Where if it doesn't work, you know, if it works, you run the team, you run this amazing product. If it doesn't work, you can always go back and go back to the core products.

    10. LR

      It's interesting

  7. 23:40 – 33:53

    PM your career like a product

    1. LR

      how your strategy here is very similar to a product portfolio strategy where as a team you should have a few big bets and then a lot of incremental stuff. And it reminds me about this awesome post call, you are in control of your career and the argument in your post is you should PM your career the way you PM your product. So there's a lot of synergy here. So maybe just diving into this post and advice around this. How, how should someone be PMing their career the way they PM a product? What's your, what's your take there?

    2. DL

      By the way, for your PM audience, I wanna say this, which is a lot of the greatest PMs are the worst PMs for their careers. They love products, they love the craft, they love, you know, the customer research, the data. They have plans, they have timelines.And then when it comes to career, they have none of those things. They just drift from job to job, "Hey, should I take this role or this role?" Like, "How do I think about this?" And, and I see the... But if I said you had to write a spec for your career, what is, what's in there, right? What are, what are your milestones? What are the skills? What are the features that you want to have with your career? You know, how are you gonna get there? What does success look like? You actually have metrics for your product, and yet you don't have metrics for your career. And so often, I often coach, um, I coach a lot of people and when I coach them, I ask them, "Well, where do you want to see yourself in five years? Where do you want to go?" And half the people have no idea, and I think that's really tragic because, you know, when you PM your career, it's about intentionality. But I'll tell you the story of my career and how I was the accidental PM, and then eventually... I told you how I accidentally fell into PM, but also fell into so many of the things that happened in my PM career, and if I had to go back, I would think much more deeply about what I want to accomplish. So, I ended up at PayPal. I was working for a guy named Dave Lee, who reported to Amy Klement. And then you know, he left, and so she offered me his role. I had only managed people for like, I don't know, 15 seconds? I was two years out of business school, and I was definitely not qualified to do his job. He was a director of product. I wasn't even a director, and I was running the, the team for eBay. So basically, the Pay- PayPal vert- ... part of eBay, which is basically half the company's revenues and, and profits. Totally unqualified. I ended up in this job, and you know, I do a good job. I end up, you know, doing it for several years. I- I build up the team, and we have a great relationship with eBay. You know, the... Our team was very close, and- and we were able to actually build something really lasting and- that worked really well. And then, I had a baby. And so, this happens in a lot of women's careers. I was turning 30, I had my son, and you know, I had to leave for s- you know, six months. And so I handed my, my product to my successor, Mike Wu, and he ended up taking over. And he did such a good job while I was gone, I didn't want to displace him when I got back. And so I thought, "Well, I'll go look for another role." I couldn't really find a product role I liked, I mean, 'cause there weren't that many product director roles. And so I ended up, um, in corporate strategy. So I worked for the amazing Rajiv, who was CEO at the time. He's since passed. And I wrote his speeches, worked on strategies. I worked on digital goods and, um, charity, and ended up building that into a vertical for the company. So charity, social commerce, and- and, um, and digital goods. And I thought, "Okay, this is an interesting job." So I create the job, have a couple of product managers, wasn't really sure where this was going, and then one day I was like, "You know what? I'm not feeling this. I have a child at home. I just..." I had gotten to the, you know, what Sheryl Sandberg calls that kind of like between kids situation, where I was bored of my job. So I go to, I go to the VP I was working, I was working for, one of the VPs I worked with, and I resigned. I said, "I'm leaving tech. Just, I'm gonna stay home and- and maybe start something small." And, uh, he convinced me to hold off, and he said, "I'll find you a job." He calls me a week later and he said, "Found you a job with Stephanie Thelenius, leading the buyer experience at eBay product." And I said, "Oh, that sounds interesting." So I said, "Sure." As you notice, I do not have a plan. I'm just drifting as... I'm so fortunate that I had amazing mentors who gave me opportunities to... But, you know, end up working for, you know, Greg Fantz and Stephanie Thelenius at eBay for two years. I led the buyer experience. We did some really good work there. And then, you know, I went on maternity leave again, and I get a call from a friend, my old engineering manager from PayPal. "Hey, I'm at Facebook. You want to come? You can't come into product. You need a CS degree for that. But you know, we have a product marketing job open." I was like, "Sounds good. Drop in to Facebook." And so again, no idea what I'm doing, back in product marketing. So I spent a few years doing that, eventually was invited into product, and you know, so, so on and so forth. And each job that came along was organic, but also kind of accidental. And I see that happen in a lot of careers, which is... My- my story, when you look back, looks great, right? It looks like it all worked out. But I had almost zero intentionality in any of these. And I think that had I had more agency and I thought about what I wanted, I could actually measure, is this the thing that would get me further or not? I ended up extremely lucky, but not everybody does. And so I think having a plan allows you to compare every decision. It's not like when you gr-... You know, when you're offered a, an admission to college and you're looking at three different offers maybe, you know, with financial aid or not, and you can make a decision, "Oh, they're offering me this department, but I can't get into this department," you know? And I'm gonna... And th- this is how far it is from home. But jobs and roles are nothing like that. It's like someone calls you one day, "Hey, I'm at Facebook. You want to come?" I'm like, "I'm actually, you know, on maternity leave." And he's like, "Just come talk to me." I'm like, "Why not?" And you know, you end up dropping into different parts of your life, and I think sometimes b- by saying, "Here's where I want to go and here's how I want to get there," you can have such a better career. And so I do encourage everybody to do this, and to think about, "What does success look like in five years, and how far am I from that, and am I heading in the right direction?"

    3. LR

      What's interesting is I also had a similar path to you, where it was... I had zero plan or intention or goal, and also just follow things, and things worked out. I wonder how often that happens, and I wonder if this idea of having intention and plan and a roadmap is something you do if things aren't working out, 'cause maybe th- maybe, maybe there's some good to not overthinking it and just following pull.

    4. DL

      (laughs)

    5. LR

      I don't know.

    6. DL

      Well, I think the problem is this with you and me, Lenny, is that hindsight bias is a problem. We made it because w- we weren't intentional in a lot of ways. But for how many people is that true, right? For how many people who aren't... you know, you don't have a plan and you get there? I always tell people, you know, if you, if you aren't sure what your destination is, that's definitely where you're gonna end up. But if you actually aim in the right direction, you can shape your learnings, you can shape the roles you take, you can shape your, you know, your skills towards the place that you want to go.

    7. LR

      Well, you... When you talk about getting this offer from Facebook, usually those are like, "You have three days to decide."

    8. DL

      Yes. (laughs) Yes.

    9. LR

      And it feels like that's when those... The things you've done ahead of time of, here's what I want, would be most helpful.

    10. DL

      And also, also I think the thing about job opportunities in particular, is they tend to come serially.

    11. LR

      Hmm. Yeah.

    12. DL

      You know, it's not like... you're presented with these offers. It's like one role is so different from another, you know, and they often don't happen at the same time. They might say, "Well, you have to decide in two weeks." And then you say, "Well, uh, there's this other company I'm talking to," and there you get a lot of pressure to say yes to this versus this. And to really having a, a measuring stick, "Is this getting me closer or further away from where I want to go?" can allow you to actually take serial decision-making to a place where you're measuring against a long-term goal.

    13. LR

      I did a meditation retreat once, and when you're meditating there's this, uh, kind of guidance of don't try too hard. Don't, don't like push yourself to go into a direction. Don't like, "Oh, this, I'm not doing a good job. I need to get to this enlightened state." And instead their advice is just like push your cart in a direction and think about that's the direction you want to head, but don't, you don't need to have, like grasp on to, "Here's what I need to... Here's where I need to land. Here's where I need to go." And I wonder if just having a thought of, "Here's where I want my career to go. I want to be on boards in the future. I want to start a company in the future. I want to become a designer in the future." Is, like at least start there maybe, just like a direction that you're heading.

    14. DL

      Yeah. There's a, there's a woman who I worked with in product and now she's a s- she's the founder, a very successful founder, and she said to me, "I want to join the board of this Fortune 100 company." She told me the company and I said, "Okay. That's a lot." (laughs) and so she said, "How can I get there?" And I said, "First, it's probably going to take you 10 years, 'cause look at who's on the board." I happen to know a couple of people on that board and I said, "Why don't I introduce you to one of them and they can tell you how to get there." But the point is, she knew where she wanted to go-

    15. LR

      Hmm.

    16. DL

      ... and she said, "I'm willing to take the first step today." And I said, "First, you've never been on a board."

    17. LR

      (laughs)

    18. DL

      "You, (laughs) you were very successful but y- this is not, you know, you have not, you know, you, there's so many steps to before you get there." It's like, before you go to Harvard, you know, you have to graduate from, you know, elementary school to middle school. You have to take the SAT. You have to apply. So I said, "Let's start from the first step and let's break this problem down." But I loved that she knew where she wanted to go and she's like, "Even if I don't make it there, I'll be happier having made this journey." And I loved that for her. And I think she's still early on in her career. She has so much time ahead of her, but it's really incredible to see her kind of on this path and to know that that's her dream and that I can help her a little bit along the way.

    19. LR

      Mm-hmm. And it also relates very much to your idea of thinking of your career like, like a PM thinks about their product where one of the tactics is to imagine the ideal scenario and work backwards from that versus like incrementally, "What's the next thing? What's the next thing?" So in this case she was thinking, "Here's where I want to l- head. Okay, what's the next thing to get to that direction?" I love that. This episode is brought to you by Webflow. We're all friends here, so let's be real for a second. We all know that your website shouldn't be a static asset. It should be a dynamic part of your strategy that drives conversions. That's Business 101. But here's a number for you. 54% of leaders say web updates take too long. That's over half of you listening right now. That's where Webflow comes in. Their visual first platform allows you to build, launch, and optimize web pages fast. That means you can set ambitious business goals and your site can rise to the challenge. Learn how teams like Dropbox, IDEO, and Orange Theory trust Webflow to achieve their most ambitious goals today at webflow.com.

  8. 33:53 – 39:19

    Challenges and strategies for introverts in business

    1. LR

      Okay, going in a slightly different direction-

    2. DL

      Okay.

    3. LR

      ... I'd, I'd say the post that you've written that has most resonated with me was about introverts and how hard it is to be successful as an introvert, and that basically you have to learn to be an extrovert as an introvert because in business, extroverts are, uh, most valued. Can you just talk about kind of your insight, what you've seen around this, and how, and your advice to introverts like me, uh, about how to be successful in business, like what you need to change?

    4. DL

      Well first, I love the book Quiet by Susan Cain. She talks about the power of introverts. Unfortunately, the world doesn't see the way the world the way she does. And I think that, you know, there is, and I, I wrote this post, and it was The Secret Bias No One Talks About, right, which is the workplace is really favoring people who can speak up. And I tell the story of somebody on my team who's just an amazing product manager, and yet every time she came up for promotion or calibration, people were like, "Oh, well what does she do?" And it was because she was not good at broadcasting or explaining what she does. And sh- I would take her to executive meetings and she was really bad at answering questions or talking, and so we would prep and prep and prep. And I just knew her skills. I could see her every day moving the product forward. But for some reason, people, you know, 'cause your peers also have influence over, you know, people's ratings and their promotions, and I was constantly just trying to figure out how to get them to see her brilliance. And I asked her once, I said, "You know, like I notice that you never answer questions when we do these presentations." She's like, "Yeah, 'cause I'm a processor. You know, and by the time I've processed, I feel like, you know, the conversation has been done." And so, you know, I really feel like the world's, it's not built for somebody like her who's a brilliant product leader, but people couldn't see it. And I realized that so much of what product and, and just general leadership is, is not just doing the work but actually it's let- and it's not just having the product, it's having great product marketing to go with it. Let's call it that. Okay?

    5. LR

      Mm-hmm.

    6. DL

      So I've been in product and I've been in product marketing, right? You make a light bulb, but you're selling light. And I, I really think about how that, she was like making amazing number of light bulbs. She was lighting up all the houses and... but she was not marketing the light, and I think that was the, the thing that was really missing. Is that fair? Absolutely not. There are a lot of people who are born introverted. Is it fair that a product manager who isn't extra- int- introverted but is an extrovert is struggling with that? No, but that's the world we live in. And so, you know, it's one of those things where you get to choose what you do. First, I think for the individual is realizing that you are your own best marketer. You have to actually share what you do. You know, if a, if a great product is out in the world but no one's told about it...... did it exist? And so one of the things that's very important is really to get that product marketing right. The second part is we should change our workplaces so everyone can be successful. And I think that that's a really important skill. As more introverts get into leadership, they need to actually change the world to make more space for people like them as well. So one of the things that I found was, you know, in my leadership teams over the last couple years, we had this thing where we all vote, but we vote offline in a document, and we put a number in, and then we put our comments in. And that way everyone has an equal voice in this document. And then when we talk about it, and usually, of course, the extroverts speak first, but you know, everyone has a vote and we can actually see what people's point of views are. And I love that. I love that when, you know, there's ... Something we used to do at Facebook is we used to go around in a circle and everybody would give their opinion in a meeting. And I do that still today. I ask every single person, "As a business leader at this company, would you do this?" And even when I, I joke with our chief legal officer, Greg, Greg. He, I say, "You know, you are a business leader and the lawyer. You can't just say, 'Well, legal advises X.'" I'm like, "But what would you do?" And so nobody can, nobody can take a backseat to decision-making. Everybody has a voice. So there's so many of these kind of bias interrupters, things that we can do to actually make the world easier for those who aren't speaking up and taking 80% of the air in the room. And I do think that we have to craft a workplace where everyone can be their best.

    7. LR

      In the post, you also talk about like, as much as we want to change the way people run their companies and thing, I love your advice of like, you also still have to learn how to speak up and act more extroverted even though it's not natural to you. Is that right?

    8. DL

      I think we do a disservice when we say we're not good at speaking up-

    9. LR

      Yeah.

    10. DL

      ... because it's a skill like any other. And if I told you the difference between your product being successful and not being successful is you giving this presentation, they're gonna kill your product if you don't sell this to the executives. You would figure out a way to stand in front of those executives and defend the freaking heck of

    11. NA

      Yeah.

    12. DL

      ... your product. But why aren't you doing that every day? And I think sometimes we forget that not everything's as essential as they're gonna cut your product if you can't convince them to keep it. But every day, you're actually building credibility for your team, getting more resources, getting more people to talk about your product inside your company, getting more press for the product outside. All of those things combine into momentum for your product. And don't you want the best thing for your product and your customers? And so if you think about it that way, it's not, "Well, I'm uncomfortable." I hear this a lot where people say, "Well, you know, you wouldn't understand. I'm an introvert." And I'm like, "So, so was I." And, but instead I just said, "Okay, this is a necessary skill, and it's a learnable skill." You don't have to be comfortable with it. You don't have to love it, but you just have to do it.

  9. 39:19 – 42:25

    Reframing self-promotion

    1. DL

    2. LR

      What about from the, another perspective of why people don't do this, which is it feels like self-promotion and it feels like icky.

    3. DL

      Yeah.

    4. LR

      Like, "I'm just sitting around promoting myself. I don't wanna be doing that." Anything there that helps people get over that piece?

    5. DL

      Well, I just remember I was, I was talking to this, um, ERG group, and, um, I, I was asking about the, it was upcoming calibration and, you know, self-reviews were due in a couple days. And I said, "Well, what are you doing for your self-review?" And somebody, somebody raised their hand and said, "Well, I'm really bad at self-promotion. How, what advice would you have for me?" And I said, "If you think your self-review is self-promotion, you've already, you're, you're just not gonna do a great job at it. What if I called it educating your manager about all the great work your team has been doing? What if I called it, you know, um, helping people see why your team should get more resources?" Suddenly you're, you're cracking open, you're changing, you're changing the question, right? From, "Oh, I was self-promoting," to, "Actually I'm helping my team get more resources and support." And suddenly she was like, "Oh. Yeah, I'd never thought about it that way." But I think often if you frame it one way, it looks like self-promotion. I wouldn't wanna do that because it's self-promotion. But at the same time, if it's education, what if I said ... You know, I was talking to a PM who's really incredible. I've mentored him and sponsored him for a long time. And I said, "I don't understand why you don't have more of a voice. Like, you've learned so much about the craft. You've done this at multiple companies." And he said, he said exactly what you said, which is, "I'm not really self-promoting." And I said, "If you see it as self-promoting, you will never do it. And so let's talk about why you don't actually do this."

    6. LR

      Mm-hmm.

    7. DL

      And he said, "I've seen a lot of people who are really great on LinkedIn, write these articles, but they have nothing to back it up, and I don't wanna be like them." And I said, "Okay, well, you read my blog. You know, you follow me on LinkedIn. Do you think I have nothing to bli- back it up?" And he's like, "No, of course not." And I said, "Well, then why do you put yourself in his category instead of mine?" And I think it was just a moment where we just came to an understanding where he, in his mind was like, "I don't want to be that person that's an empty vessel that has like nothing, no substance behind it." And I said, "Do you think the things I write have no substance?" And, but it was an interesting conversation, because he had taken this mantle that it was self-promotion and that behind, "What if people think I have nothing behind it?" I'm like, "I know you have something behind this. I have been your manager. I have worked with you for many years." But you see how just reframing it has really changed his way of thinking about it. Still working on him, but I actually think he has so much to give and I think he, he has learned so much about the craft, and I wish that more product managers felt comfortable that they have something to give to the world.

    8. LR

      I think what you're saying right now will resonate with a lot of people when they see people posting ... Like, I feel this still, of just like, "I don't wanna be this guy that's just posting nonsense on LinkedIn just to get likes," even though it's kind of what I do now full time.

    9. DL

      (laughs)

    10. LR

      Hopefully it's not nonsense. But if-

    11. DL

      But it is all substance, so letting me know that there's-

    12. LR

      It's al- I try.

    13. DL

      ... substance behind it.

    14. LR

      But I, I think there's like a posting on LinkedIn, posting on Twitter. It's just like, there's like an innate, "I'm just doing this 'cause I want to get attention," when often, and the way I started this is just like, "I have things I've learned that I think are useful. I'm just gonna put them out there."

  10. 42:25 – 46:15

    The power of accountability

    1. LR

      Uh, so just to double click a little bit, 'cause I think this is a really powerful point. What actually have you found helps people get over that? Is it like someone like you in his corner being like, "You have really great stuff to share. You should actually do it. Don't be as worried as you are."... as you think you might be? Is there anything else that works there?

    2. DL

      Actually, what worked for me was I was working with Boz. And I talk about our relationship in my book. Um, but I, you know, we, we made a contract when I started reporting to him. And Boz, for those of you who don't know, is currently the CTO of Meta. At the time, he was the head of ads and, and then our team moved into his team. And so I was reorged into his, his, uh, organization. And as I said, you know, um, we did not have the best relationship before that. And so we made a contract to work together. And I had written like, "Here's how, here's how I want you to take care of my team. Here's how I want you to support our products." And I wrote him, like, this long... my part of the commitment. And then he wrote back, "Here's what I'm asking of you. I want you to write and publish something every month." And I was like, "What are you talking about?" (laughs) Like, "Why would you say that?" And he said, "You have so much to teach people, just do it." And I said, "I don't really have that much to say." And he's like, "Just trust me on this. You'll figure it out." And so his advice was: write what you repeat. If you say something more than once, just write it down. And then just, you know... then the next time someone asks you, you can just hand them

    3. NA

      Yep.

    4. DL

      And he has a great blog if you haven't read it. I just remember thinking, "That is a weird thing for your new manager to say, after you had a lot of conflict together before that." But he took my contract, which was by the way, he's like, "Oh, do you wanna, like, codify this in some way?" I'm like, "No, I just..." So, but every month from then on, I would literally just write something. And it was my promise to him, and I did it faithfully and I published it internally. So I didn't publish it externally for a long time. And then sometimes he would ask me if I want to publish it externally from the company, and I would say yes. And so I did it for years, I reported to him for years, and then, you know, we switched managers. He moved over to Reality Labs, and then I had a new manager and, and I continued, and I've continued this, you know... Then I started doing it publicly, and then obviously I wrote a book and, you know, because of him and his encouragement, it got me to a totally different place. And part of it was just the commitment. I now had accountability 'cause I knew he was watching. I'm not actually sure if he was actually watching every month, but I felt the accountability to do this. And I've done it every single month since.

    5. LR

      So, it's interesting that that's another example of your manager giving you the space/forcing you to (laughs) share publicly, being a really good lever to get someone over this fear.

    6. DL

      I think sometimes just doing it gets you over the hump.

    7. LR

      Yeah.

    8. DL

      Like for example, my friend Ami Vora, she writes an incredible blog. If you have not read her Substack, you should. But, um, she's an incredible writer. She'd write all these things internally and I said, "You should publish this externally." She has... now she does that and it's really great. And I think part of it was just seeing her just put it out there, because she is one of the wisest career coaches that I have... and managers that I have ever worked with. And so I'm like, "You have so much to say and to share." So to see it out there, I feel like for years we all got the benefit of it 'cause we knew her, but, you know, the world was not getting the benefit. So in some ways just having accountability. So we created a little accountability group to, like, help each other write. And it was just a reminder, "Hey, did you do it?" You know? And so I think it's sometimes what's necessary to get over that hump, is either having someone forcing you, like your manager who you made a commitment to, or just having a friend to say, "Hey, by the way, where's this month's post?" Those things matter, because now you got over the hump of, "I have to do it," and now it's just about how good you're gonna make it and how much time you're gonna put into it.

    9. LR

      Awesome advice. And by the way, folks who don't know, we've had both Boz and Ami on the podcast in the past.

    10. DL

      Yay.

    11. LR

      And, uh-

    12. DL

      And aren't they both amazing?

    13. LR

      Amazing. And Ami's episode is one of the most popular episodes, h- more popular than Boz, CTO of Meta. What do you know?

    14. DL

      I know. Well-

    15. LR

      Who would've thought? Um...

    16. DL

      She has a lot of coaching wisdom I think that everyone should hear.

    17. LR

      Yeah, she's amazing. She ha- yeah, and she has a great Substack. We'll link to it again in the show notes. And we'll link to your Substack as well.

    18. DL

      Yes, please do.

    19. LR

      Go Substack.

  11. 46:15 – 50:52

    Growth: a game of inches

    1. LR

      I wanna move in a slightly different direction, talk about growth for a little bit. You have a really nice perspective on how to think about growth. I think a lot of people think of growth as like, "Here's a magic bullet. We're gonna do this thing, it's gonna go wow, we're gonna win." And your approach is it's, you talk about it's a game of inches, growth is a game of inches. Can you talk about your perspective there?

    2. DL

      Yeah. You know, sometimes we think it's like, what is the huge step function? But actually most companies are like, th- we call it points of growth, right? It's like if you can move things 1% a little bit faster every single week, think about the amount of growth you get at the end. And so it's not just, you know, okay, what's gonna get you the three X? You can get to three X 1% at a time, 5% at a time, single digit growth. And sometimes it is the small things that matter the most. And so when we think about product-led growth, it's really about finding the, the aha moments, the opportunities. And sometimes those opportunities are things that seem really silly. I heard this story at Facebook that one of the big things was just adding the... next to ads, they put the word "create an ad." You know, it was like one of the biggest growth drivers.

    3. LR

      Mm-hmm.

    4. DL

      And that was it. Just putting a link, because people just didn't know how to get to the ads flow. And, you know, it was things like that where you can actually bend the curve of things, choices that you make. Same thing, you know, each of the growth teams I've ever worked on, it's like really the small things adding up. It is a list, we used to work on payments growth, and we had a list of 100 things we were working on, uh, hypotheses, and that we would pick and we would grow them by picking the first 10 and we would start working on them. The next 10, the next 10, and we would go through these sprint cycles. And the same thing when we were growing the ads product as well. Marketplace, each of them were just like, what are the small things that add up to big things? And I think sometimes we overthink it. Instead, you probably have 100 ideas. And by the way, it is absolutely okay if, like, 80% of 'em don't work. I tell people, like, sometime we, we overthink as product managers, right? If we just had the perfect plan, the perfect battle plan. But instead, imagine you're a team and you can ship, I don't know, like, let's say four things. But what if you're a team that can ship 20 things with the same... with a 20% success? You get just as much output, and yet you now have, you know what doesn't work also. What if you can move it from 20% to 30%? Suddenly six things work, not just four things. And so in the same amount of time, you have all the lessons of what didn't work, plus you're getting 50% more output. And so you're thinking about growth as this engine of, it's a learning machine-... of what doesn't work, what you iterate on, what you change, and you're constantly getting better and better and better.

    5. LR

      I think what you're saying will resonate with a lot of product people, where there's always this like, "We're just doing a bunch of optimization, incremental work, it so sucks, boring, why would we? Let's take some big bets." And, uh, in my experience, and sounds like in your experience, a lot of the wins act- ... And Facebook is famous for this, just like const- relentlessly looking for ways to, uh, grow, grow, g- like optimize, optimize, optimize, 'cause that's where a lot of growth comes from. At the same time, obviously you need to take some big bets and take some swings and look for step function changes. But I guess for someone that's just like ... I don't know, is there any advice on just creating that culture of like, it's okay to optimize for a long time, there's a lot of opportunity optimizing? Is there anything you've learned there or is it just like bring in a dev and like ... so it has to be a top-down?

    6. DL

      Well, I treat growth like a, like let's say a product marketing team, right? It is an augmentation for a product that works. So if you have a core product that works, you have a team that's working on ... So for us at Ancestry, it's like search and hints are the core. You know, what i- what is the mechanics? You want people to add, you know, people to their family tree, you want them to add stories. Okay, there's teams that make sure that the uptime is good, that the hints are working, the search delivers results. And you need those teams, you need those core teams kind of functioning. But growth is a, is, is actually optimization on top. It is making it so that you get to the search flow faster, that hints are surfacing better, that people are accepting them, that if we put the button here versus here that people are gonna discover things faster. And so it's really taking the core engine and actually wrapping it around the user interface, around the experience, around the flows, so that people can get to it faster, they can have more satisfaction, they can have more impact. And that's what I see growth as. It's not the core product, it is the cherry on top making that product more accessible and more usable and better every single day.

    7. LR

      Yeah. Kind of along these lines, I think it surprise people to learn there's like at least 100 people at Airbnb just working on like pricing, optimizing the pricing recommendations. There's like endless opportunity to just make all these core components of an experience better and better and better over time.

  12. 50:52 – 56:52

    The 30-60-90-day plan

    1. LR

      Okay, last thing I wanna talk about, and this is like completely unrelated to everything we've been talking about mostly, which is your 30/60/90 day plan. So you wrote this post a while ago of just like here's a great 30/60/90 day plan when you join a company. And I've heard that many people use this. It's really effective for helping someone onboard and be successful. And I think it's mostly for execs, or is this for just anyone joining a company?

    2. DL

      It's for anyone. I ac-

    3. LR

      Okay, anyone.

    4. DL

      I created it actually when I joined Ancestry, because I hadn't started a real new job in 11 years. And I thought, "I'm gonna be a student of how to land well." So I read a bunch of things, I read, you know, it's like the ... And I decided I was gonna adapt all of those things into a, a summary and then I was gonna try it real time in my blog. So in my blog, I write, "Here's what I'm gonna do," and then I tell you what I did and how it worked. And some things that ... And then I actually do a look back as to all the mistakes I've made. And so I kinda did this live. It was not ... kinda it was not planned quite as, as well as I would thought. But I put it together and I, I wrote the 30/60/90 day plan, and I have a template. And it's really ... I always tell people like it's focused on listening and learning first, and then doing. And so that's the crux of it, which is in those 90 days, it's like, you know, you gotta get used to the environment. You wanna have some impact at the start, you wanna have a couple quick wins, but you wanna understand the lay of the land and you wanna listen. Because you're y- you know, you have something to contribute, but if you don't understand the language, you don't understand the culture, you might actually make huge mistakes. And so for the first 30 days, I did a listening tour. Listened to ... you know, I talked to over 60 people in 30 days, and then I summarized, you know, a state of the union. "Here's what I'm hearing. Here are the challenges people feel like we're facing. Here are, here's what people's wish lists are." And by the way, one person sent me a wish list of five things, and at that year, I think it took me till year two to finish his five things. And then I sent him a note, I said, "By the way, the first time we met, these five things you wanted to see, we just finished the last one." And he's like, "I can't believe you remembered me." I took extensive notes and I summarized it, and I think it's important because people wanna hear that you hear them. And you don't have to be, you know, a manager or CEO to do that. I think people on teams often feel like there's no outlet for the things that they wanna, they wanna say. And I encourage especially product leaders, especially if you're joining an existing team, to listen really behind what people are saying. You know, and then offer to help them do one thing. So especially when you're meeting with a, a new engineering team for the first time, actually ask them, like, "What is one thing I can do to help you this week?" I would say one thing, so it's limited. This week, so getting 50 new headcount, probably not gonna happen. And it's like, "How can I give back?" And suddenly you're building a reciprocal relationship. And so a lot of this 30/60/90 day plan is really to help you find your footing, and then to start having impact immediately.

    5. LR

      Say you join a company and you're like, "I'm gonna do 30 days listening," and then your boss is like, "No, we need to ship stuff. Get on it, ship this stuff." Is there any advice for trying to push back on that create space for listening when there's like deadlines, things are on fire, like ... Uh, it's tr-

    6. DL

      I encourage everybody to get on the same page on this 30/60/90 day plan with their manager.

    7. LR

      Mm-hmm.

    8. DL

      So actually don't just keep it to yourself, share it with as many people as you can, 'cause I think it's very important that everyone sees what you're trying to accomplish and what your output is gonna be. 'Cause if you don't know the output, are, is success there? The second part is, you know, with your manager, say, "Okay, I would like to carve 20% of my time listening, and I'm happy to do this work 80% of the time. Therefore, you know, every morning from 9:00 to 10:00, I wanna, you know, talk to somebody, somebody in the organization." Just make sure you say, "I will do a better job and have more impact if I have this time to make sure that, you know, I'm not accidentally making, you know, mistake or I don't, you know, I didn't get a chance t- I'm asking something of somebody but I've never met them." And to really, you know, carve out space, because it's really important. Once you're in it, you tend ... People give you kind of the new person card for maybe a month or two-And then suddenly, it's all the problems are your problems. But what if you don't know what the problems are? And so I always say, you know, diagnose before you treat. So make sure you understand so that you can help and deliver what your manager is actually expecting of you.

    9. LR

      I'm looking at your template, so just to, uh, share the bucket. So first 30 days learning focus, second 30 days is aligning on vision for the future, and the last 30 days of the 90 days is executing, setting up, ac- like actually getting, starting to get stuff done.

    10. DL

      Yes.

    11. LR

      Awesome. Uh, anything else along these lines of this?

    12. DL

      The one thing about having a plan also is that you don't feel rushed to-

    13. LR

      Mm-hmm.

    14. DL

      ... you know, do something that you're not n- ready for. Because I do think sometimes you feel like you need to have impact. And I always say, I always tell people, like, "Do something small. Like give back in some ways where people see you making, you know..." But when you actually reflect, one of the biggest things I could do was actually reflect back to the organization, "Here's what I heard from all of you. I'm listening, I hear this, and here's what I want to do about it." And then in aligning, it's like, "Do we agree this is a set of problems we want to tackle?" And then on execution is like, "Do we agree that this is how we want to move forward?" And I think that is such an important part of building a, building into a team. You know, when you enter an organization, you're also entering a team, and you're part, you know, you're part of a dance that's going around. What role do you play? And people are dancing around you, and if you, if you actually make a mistake, you could trip other people up as well. So really kind of finding your place in the dance is really important.

    15. LR

      And as a, as a PM, the way I always think about it is people don't, will ass- won't assume they should trust you. Like, you're just this person that's coming in to kind of tell them what to do. And so much of your first month, two, three is building that trust with people so that they can actually feel comfortable listening to your guidance and not just like, "Oh my God, this person's getting in my way."

    16. DL

      And earning that trust, you know, sometimes people really, uh, you'd be really surprised. A lot of people feel like they're, they're not heard. And even just coming in and listening is a trust-building exercise.

    17. LR

      Such a good point.

  13. 56:52 – 58:57

    Contrarian corner: career and marriage

    1. LR

      As we wrap up our conversation, just w- couple more questions here. So first is I want to take us to Contrarian Corner, which is a segment on this podcast. And my question is just, is there something that you believe that you think most other people don't believe? Something that you think is a contrarian perspective?

    2. DL

      So I don't know if this is a contrarian perspective, but I tell, um, I go to speak in a lot of, um, universities, so I speak at Stanford and going to speak at Duke, and I always tell people, especially young people, "The most important career decision you make is who you marry." And it's not something we think that much about. Especially, I started dating, I met my husband when I was 18, my first weekend-

    3. LR

      Oh, wow.

    4. DL

      ... in college.

    5. LR

      Mm-hmm.

    6. DL

      Started dating when I was 19. I, we had no idea what our life was gonna be like. And yet, every single day, like this week, we had our board meeting, I was in Utah the whole week, I come home, and you know, he's taking care of everything, right? And it's that, you know, you will have a much more successful career if your home life is in balance. It's like a yin and a yang, right? If something is out of balance, it, it engulfs the other side, both your job and your home life. And especially, you know, we have three kids, really, really balancing that is very hard over both of us having demanding careers. And I think we just, it's not something that's contrarian, but it's something which we don't think about at all when we make that decision. We think, "Is this person fun to be with? Is this person, you know, somebody we see ourselves with?" But my question is, what is the impact of this relationship on your career? Is this person lifting you up or pushing you back? Is this person someone who's gonna be your greatest cheerleader or are they gonna be the greatest weight on, on you? And how do you think that that's gonna manifest itself 20 years, 30 years from now? And I think it's just something I wish we thought about more, and I encourage especially young people to think about that.

    7. LR

      Such a great point, is... What I want now is a, a guide for vetting these things when you're dating.

    8. DL

      (laughs)

    9. LR

      Deb's Guide to Dating.

    10. DL

      (laughs) I need to write that. Although I've only really dated him and one other person, so maybe I'm, I'm like the worst person to tell you that. (laughs)

    11. LR

      But it, but it worked, so you're maybe the best person, and now you can-

    12. DL

      But who's to say? That's right.

    13. LR

      ... look back and here's the questions I asked that worked. Um, that's

  14. 58:57 – 1:03:09

    Final nuggets of wisdom

    1. LR

      so funny. Okay, so before we get to our very exciting lightning round, is there anything else that you think might be helpful to share? Something you might want to leave listeners with? Any other nuggets of wisdom or advice?

    2. DL

      Well, there's one quote which I share, which, um, I thought about when you were speaking earlier, which is about, um, you know, people who are resilient, which is life... This is a quote from Chuck Swindoll. He's a Christian writer that I used to read a lot, and it was, "Life is 10% what happens to you and 90% what you, how you react to it." And I just looked him up, uh, recently, and, and, uh, he, he actually published a book with that quote. He actually had that quote in a previous book from 20 years ago. And I just think that's so important. You know, you don't get to choose everything that happens in your life. So much of it is just, it just happens, and, but it's the people who choose a way forward to turn stumbling blocks into stepping stones, as I said. Somebody who actually says, "You know what? I didn't get the job that I wanted, and I'm just going to figure out another path." Those are the people who have the most successful and satisfying careers. They're zigging when other people are zagging, you know, and vice versa, and I think that they're, you know, are the ones who are the most resilient and happy in the long term.

    3. LR

      It's such a good, uh, circle back to one of your first pieces of advice of just most successful people are people that are resilient and don't avoid failure but embrace it and find a way to turn it around. I think it's such an important point. It's so hard to do. I guess just, I don't know, just to follow this thread a little bit, is there anything that has helped you build that or has that always been the way your mind worked? I imagine, like, coaching helps this, helps people with this. Is there anything just like how to build...

    4. DL

      Coaching is incredible for that.

    5. LR

      Hmm.

    6. DL

      We joke it's work therapy. But really-

    7. LR

      Yeah.

    8. DL

      ... I think it's, you know, for a long time, I just, I saw failure as this, like, catastrophic thing. Like, I was one of those kids who's like, you never got a B, until I, you know, then I got to college and I was like, "Wow, this is harder than I thought." And so I got two Bs in college and I'm like, "I'm never doing that again." You know? But I was that kid who always got the A, who got the great scores. I just thought that my life would end if I got a B, you know? And, uh, which by the way is super unhealthy. And looking back, I realized that, like, work is not like that at all.... and every time I got bad feedback, I'm like, "This is catastrophic." But if you look at feedback as an opportunity, then it's very different. It's like, this is a gift, right? But you can't... I would just, I would be crushed. Every time we get a review, no matter what rating I got, I would read the things that people would say, and I was like, "Oh my gosh, I'm a terrible person." And I had to really rethink that, and I think coaching, l- leadership coaching, has really helped me through that to say, "No, how do you process this? And how do you get to the other side?" And that has been so transformative for me, is to have that outlet to actually talk through, "No, no, no. What they're saying is not that you're a bad product person. It's that you need to do a better job communicating or connecting," and, and I really struggled with that. I was very transactional. I was not a connector. I was not warm. I really struggled with relationships. And a lot of the feedback I received for many years was this relationship issue. And it took me a long time to realize that people weren't saying this because I'm a bad person or that they hate me, but because they want to connect. And I was actually making it hard. And I think sometimes we take things so personally that it becomes kind of this thing. It's like your, it's, it is your white whale. It's like the thing you're chasing. But then what if you say, "You know what? I don't need to do that. I don't need to chase that. Instead, I need to figure out what's behind the feedback and what are they trying to say?" And then actually change yourself over a long period of time towards that.

    9. LR

      I, I had similar challenges where I had this pretty real imposter syndrome for a while when I got, when I started doing well, and a coach is the key, was the key for me to help me get over that and see that if I made a mistake, things wouldn't crumble, and that it's very normal to make mistakes. (laughs) Nobody will-

    10. DL

      And o- by the way, I think-

    11. LR

      Yeah.

    12. DL

      ... perfectionism is a curse we place on ourselves, and it's a very dangerous thing, particularly for products, product leaders, because product managers, you know things are gonna go wrong. That's literally part of your job. And yet, when we have perfectionism, it is a lack of trust in our ability to bounce back and our ability to actually adapt. But the more adaptable you are, the less you have to be perfect every single time.

    13. LR

      Hmm.

  15. 1:03:09 – 1:04:47

    How to find a coach

    1. LR

      Just to leave people with a tactical piece of advice. Say they are like, "Oh, man. I need a coach." Do you have any advice for how to find a coach, how to explore that route?

    2. DL

      Yeah, so I actually wrote an article 'cause one of the things I, I struggle with, coaching is very expensive often, and not every company provides it. My husband actually works at a coaching company called Sounding Board to make it more accessible, but one of the things I encourage people to do is there are other ways to get coaches. So one is go... You know, I'm in a Lean In group, and we're just like, we support each other. I'm in a coaching circle in YPO, so, um, that's like a, a group of CEOs, and I'm in a number of these coaching kind of circles which give you an opportunity to learn from each other and to get peer coaching, and I think that's a good, great place to start, especially earlier in your career when you're seeing kind of the same people making the same mistakes. I think as you get more senior, you know, having an individual coach helps because the, the situations are so much more unique. But I do think that having that outlet, having a place to say, "Hey, is it me? Or is the situation not right?"

    3. LR

      Hmm.

    4. DL

      "And how should I think through this?" That's so incredibly important.

    5. LR

      I'm lis- I'm listening to this bo- or reading a book called Listen right now-

    6. DL

      Mm-hmm.

    7. LR

      ... that a previous guest recommended. It's a parenting book, and it's about-

    8. DL

      Oh.

    9. LR

      ... just the power of listening and how much that solves many problems. So with your challenges or with your child, when your child is having a problem, just listening to them, uh, there's a lot of power. This came from a coach that was on the podcast recently, so we'll link to that.

    10. DL

      Sounds great. I'll definitely-

    11. LR

      Yeah. He's, he-

    12. DL

      ... I'll, I'll read it or listen to it.

    13. LR

      (laughs) Yeah. I know, it's weird. I'm like, "Reading?" It's called listening. Yeah. He's like, "This is the parenting book, the only parenting book you need, really. It solves all the problems that we deal with." So anyway, uh, that was an awesome final nugget (laughs) that w- uh, I'm glad we got

  16. 1:04:47 – 1:06:13

    Lightning round

    1. LR

      there. With that, though, we've reached our very exciting lightning round. (lightning strike) Are you ready?

    2. DL

      Okay. Let's do it.

    3. LR

      Let's do it. (laughs) First question, what are two or three books that you've most recommended to other people?

    4. DL

      So, um, I love the book from, uh, Professor Jeffrey Pfeffer. I speak in his class now, but I read it way before that. It's called Power: Who Has It and Why, and I love the book. He actually has a more practical one, 7 Rules of Power, which came out more recently, and so just it's a book that reminds us that, you know, power is not accidental, that people often get it for different reasons, and how you should think about the playing field. Um, another book is The Conversation. Uh, Dr. Livingston wrote that about race in America, and I just love that it's a very honest assessment of race in America. It is a really tough, you know, it's hard to have that conversation, and I love that he uses a lot of facts and, you know, and encourages people to open up and have conversations around it. And then the last one I would say is, well, Susan Cain's Quiet. I adore the book because, you know, I do have introverted kids. I, myself am introverted, and just to read, you know, the power of introverts is a reminder that we do have amazing people who don't communicate the same way. And I love that it's a tribute to those, those, uh, the success of those, even if our workplace is not adapted to it. I do think we need to adapt to it so that we can bring the best in everybody, but her book is a reminder that there's so much power even in, in silence.

Episode duration: 1:11:25

Install uListen for AI-powered chat & search across the full episode — Get Full Transcript

Transcript of episode MajB5CQUKDA

Get more out of YouTube videos.

High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.

Add to Chrome