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Leveraging mentors to uplevel your career | Jules Walter (YouTube, Slack)

Jules Walter is a product leader at YouTube and co-founder of both the Black Product Managers Network and Codepath.org. Previously, he led monetization and mobile growth teams at Slack. He’s also a very well-known leader in the broader product community. In today’s episode, we discuss the skills that matter most to PMs, and how to build those skills. We also spend quite a bit of time talking about the importance of finding mentors to help you learn new skills, how to nail your next job interview, barriers to entry for underrepresented people, and some of the most common paths into product management. — Find the transcript at: https://www.lennysnewsletter.com/p/leveraging-mentors-to-uplevel-your — Thank you to our wonderful sponsors for supporting this podcast: • Vanta—Automate compliance. Simplify security: https://vanta.com/lenny • Notion—One workspace. Every team: https://www.notion.com/lennyspod • Linear—The new standard for modern software development: https://linear.app/lenny — Where to find Jules Walter: • Twitter: https://twitter.com/julesdwalt • LinkedIn: https://www.linkedin.com/in/juleswalter/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — Referenced: • Maryanna Quigless on LinkedIn: https://www.linkedin.com/in/quigless/ • Brittany Bankston on LinkedIn: https://www.linkedin.com/in/brittany-bankston-77693a85/ • Benin Saffo on LinkedIn: https://www.linkedin.com/in/benin-saffo/ • Lawrence Ripsher on LinkedIn: https://www.linkedin.com/in/lawrenceripsher/ • Matt Mochary on Lenny’s Podcast: https://www.lennyspodcast.com/videos/how-to-fire-people-with-grace-work-through-fear-and-nurture-innovation-matt-mochary/ • Adriel Frederick on Lenny’s Podcast: https://podcasts.apple.com/us/podcast/humanizing-product-development-adriel-frederick-reddit/id1627920305?i=1000583287891 • Bangaly Kaba on LinkedIn: https://www.linkedin.com/in/iambangaly/ • The Minto Pyramid Principle: Logic in Writing, Thinking, and Problem Solving: https://www.amazon.com/Minto-Pyramid-Principle-Writing-Thinking/dp/0960191046 • Pathwise Leadership: https://pathwiseleadership.com/ • Erin Teague on LinkedIn: https://www.linkedin.com/in/erinteague/ • Bradley Horowitz on LinkedIn: https://www.linkedin.com/in/bradleyhorowitz/ • Nikhyl Singhal on LinkedIn: https://www.linkedin.com/in/nikhyl/ • Tim Ferriss on what makes a great mentor: https://www.businessinsider.com/tim-ferriss-what-makes-great-mentor-2017-11 • Never Split the Difference: Negotiating As If Your Life Depended on It: https://www.amazon.com/Never-Split-Difference-audiobook/dp/B01COR1GM2 • Connect: Building Exceptional Relationships with Family, Friends and Colleagues: https://www.amazon.com/Connect-Building-Exceptional-Relationships-Colleagues/dp/0241986869 • Chris Voss’s MasterClass on negotiating in the workplace: https://www.masterclass.com/sessions/classes/win-workplace-negotiations • Lex Fridman’s podcast: https://lexfridman.com/podcast/ • Never Have I Ever on Netflix: https://www.netflix.com/title/80179190 • Top Gun: Maverick on YouTube: https://www.youtube.com/watch?v=0KBTJBiL3oQ Interview Prep Communities: • Lewis C Lin's Interview Community: https://join.slack.com/t/pminterview/shared_invite/zt-1mqc5lzdt-SZuIvbzZIl8ob7UJeydVGg • Exponent: https://www.tryexponent.com/ • StellarPeers: https://stellarpeers.com/ — In this episode, we cover: (00:00) Jules’s background (06:07) Two paths to becoming a product manager (07:20) How Jules became the first growth PM at Slack (09:03) Black Product Managers Network and Codepath.org (12:05) The most important skills to refine as a PM: IQ skills and EQ skills (14:48) How to improve your interview skills  (18:50) Why interviewing is more difficult for underrepresented people (20:39) EQ skills: what are they and how to improve them (22:44) The EQ skills Jules has had to develop over the course of his career (24:27) The importance of having a mentor or coach for self-reflection (26:09) How cultivating self-awareness helped Jules improve his communication (30:13) Strategies for learning new skills (35:32) Improving strategy, execution, and product sense (37:00) How identifying best practices can help you improve skills (40:22) Communicating clearly and asking for feedback (42:38) Methods Jules uses to improve skills (45:31) How to approach asking for feedback (47:46) Why it’s harder to get honest feedback on EQ skills (50:56) The importance of understanding your strengths and weaknesses and leaning into the former (55:18) Jules’s most impactful mentors (56:14) The qualities to look for in a good mentor and how to approach them (1:02:15) How to foster the best relationship with your mentor (1:06:51) Lightning round — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Jules WalterguestLenny Rachitskyhost
Jan 5, 20231h 10mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:006:07

    Jules’s background

    1. JW

      If you give me feedback, I'll be like, "Hey, thank you so much. This is super helpful." Because people are like, "Oh, he actually likes the feedback." Now, in- inside, my heart might be melting, you know? And I'm like, "Oh, I thought I was dead at this." You know what I mean?

    2. LR

      Yeah.

    3. JW

      But externally I'm like, "Hey, thank you," and I mean it. And I think that's the key that most people don't focus on. And if you get more feedback, then you'll just get better at the things.

    4. LR

      (Intro music) Welcome to Lenny's Podcast. I'm Lenny, and my goal here is to help you get better at the craft of building and growing products. Today my guest is Jules Walter. Jules is a product leader at YouTube. Before that, he spent four and a half years at Slack, where he was their first growth PM, and then went on to lead their monetization teams and also their mobile team. He's also the co-founder and a board member of the Black Product Managers Network and Code Path, both of which are nonprofits that aim to increase diversity within tech. Jules and I have collaborated on a number of projects over the years, including a killer guest post on building product sense that continues to be one of the most shared and beloved posts in my newsletter. In our conversation, we focused on what skills matter most in advancing a PM's career, and more importantly, all the ways Jules has found to build those skills. We also go deep on mentorship, how to find a mentor, what to look for in a mentor, how to get someone to agree to be a mentor, and a lot more. I super enjoyed this conversation, which I'm sure you can tell. And Jules is such a gem of a human. I can't wait for you to hear this episode. With that, I bring you Jules Walter after a short word from our sponsors. (Upbeat music) This episode is brought to you by Vanta, helping you streamline your security compliance to accelerate growth. If your business stores any data in the cloud, then you've likely been asked or you're gonna be asked about your SOC 2 compliance. SOC 2 is a way to prove your company is taking proper security measures to protect customer data, and builds trust with customers and partners, especially those with serious security requirements. Also, if you want to sell to the enterprise, proving security is essential. SOC 2 can either open the door for bigger and better deals, or it can put your business on hold. If you don't have a SOC 2, there's a good chance you won't even get a seat at the table. But getting a SOC 2 report can be a huge burden, especially for startups. It's time-consuming, tedious, and expensive. Enter Vanta. Over 3,000 fast-growing companies use Vanta to automate up to 90% of the work involved with SOC 2. Vanta can get you ready for security audits in weeks instead of months, less than a third of the time that it usually takes. For a limited time, Lenny's Podcast listeners get $1,000 off Vanta. Just go to vanta.com/lenny. That's V-A-N-T-A dot com slash Lenny to learn more and to claim your discount. Get started today. This episode is brought to you by Notion. If you haven't heard of Notion, where have you been? I use Notion to coordinate this very podcast, including my content calendar, my sponsors, and prepping guests for launch of each episode. Notion is an all-in-one team collaboration tool that combines notetaking, document sharing, wikis, project management, and much more into one space that's simple, powerful, and beautifully designed. And not only does it allow you to be more efficient in your work life, but you can easily transition to using it in your personal life, which is another feature that truly sets Notion apart. The other day, I started a home project and immediately opened up Notion to help me organize it all. Learn more and get started for free at notion.com/lennyspod. Take the first step towards an organized, happy team today, again, at notion.com/lennyspod. Jules, welcome to the podcast.

    5. JW

      Hey, Lenny. Thanks for having me. I'm really excited.

    6. LR

      I am even more excited. This chat has been a long time coming. I've been hoping to get you on this podcast ever since this podcast even launched. And then in the meantime, while we've been waiting to schedule it, a number of guests have mentioned how useful you've been to them in their career. And so, I'm just really excited to finally have you on.

    7. JW

      Yeah, same here.

    8. LR

      Let's just start with a quick overview of your background. Could you share some of the wonderful places you've worked, some of the wonderful projects you've worked on, and then just a bit about what you're working on today?

    9. JW

      Yeah, happy to. Um, so some quick background. Grew up in Haiti, studied computer science in college, went to business school. My first career was actually not in tech. It was in medical devices. I was a GM for a company based out of France, and also overseeing West Africa business for them. After doing that, I moved back to the US, launched my own startup, which didn't work out, and then I moved to the Bay Area roughly eight years ago. And in the Bay Area, I wanted to become a PM, which was really hard to get into. So, at first, I joined a startup, Series A company, became head of product for them, uh, and then joined Slack as the first PM on their growth team. And then, from there, helped scale the growth team at Slack. When I joined, revenue was around 15 million. When I left, roughly four years ago, it was 10X that. And then, after Slack, I, uh, recently joined YouTube Google about two years ago. And at Google, I'm a product lead at YouTube, where I, uh, I'm driving a product called Primetime Channels, which actually recently launched in November in the US. And in that product, we're bringing streaming services to YouTube, so that users can watch their favorite movies, shows, and sports content.

    10. LR

      Amazing. So the reason that I think we pushed this schedule of this podcast recording out is 'cause you've been working on that product for many months. (laughs)

    11. JW

      Yes.

    12. LR

      And I'm glad to hear that it's finally launched. How did the launch go?

    13. JW

      So far, so good. Um, it's really exciting to take a product from nothing to something.

    14. LR

      Especially at a company like Google.

    15. JW

      Yeah. And then, over time, we're, we're adding more exciting content onto the product. We just recently announced that we- we're, we're adding, uh, NFL Sunday Ticket in 2023 to Primetime Channels and also to YouTube TV, so it's been a really exciting project.

    16. LR

      That's awesome. I bet there's

  2. 6:077:20

    Two paths to becoming a product manager

    1. LR

      a lot of stories there, but I know you can't talk too much about what's happening at Google, so we'll move on. I like the point that you made about joining a startup. Like you were trying to get into product management and you joined a startup as their first PM, I think you mentioned. That's how you got into the PM path. That's... Or I guess, correct me if I'm wrong, but that's an interesting example of one of the paths into product management, joining a startup, getting into product there.

    2. JW

      Not as their first PM, but I joined as one of their first PMs, yeah.

    3. LR

      As one of their first PMs.

    4. JW

      Yeah.

    5. LR

      So yeah, that's something I hear often, is just one of the paths of product management is join a startup, start doing product and then you're a PM, and then you have a PM on your resume, PM title on your resume and you can now join other companies. Is that something you found too or anything you can take away from that experience?

    6. JW

      Yeah. It's really, really hard to get into product.

    7. LR

      (laughs)

    8. JW

      Uh, and there isn't a really set path to do that. So what I've seen is the path that we just talked about, join a startup and then from there go into different companies, and then the other path is, that is typical, is being at a company and then switching to product management, especially if you develop domain expertise, uh, and there's a need for a PM. So that's even more frequent. Of course, there's also, you know, acquisitions, you know, that sort of thing. But making that initial transition is really hard.

    9. LR

      I didn't realize you were the

  3. 7:209:03

    How Jules became the first growth PM at Slack

    1. LR

      first growth PM at Slack. That is a big role. How did that work out? How did you become the first growth PM at Slack? Was that the first time you were doing growth? What's the story there?

    2. JW

      I joined Slack early 2016 and the role that was available (laughs) at the time was growth.

    3. LR

      Hmm.

    4. JW

      I did not know anything about growth, but I was like, "Hey, you know, this is my, my way in. I'm at such a great company." So that's, you know, what I joined to do. And then what I, what I did there was really take a learning mindset and, you know, lean on mentors, and we can talk about that, to really learn the, you know, the practice of growth and apply it for Slack.

    5. LR

      Cool. We're definitely gonna talk about some of those things. Just thinking about that experience and that ride at Slack, what's, like, maybe the most tangible memory or most, I don't know, interesting story of just, like, riding that rocket ship of Slack growth as one of the early PMs?

    6. JW

      There's many, many stories. My experience was I got in, didn't know much about growth, and then through mentorship, in particular one mentor, Bingali Kaba, sort of learned how to apply growth frameworks to my work. And then when I did that, within six months, I was able to ship changes in the new user experience, especially on mobile. That moved the needle by a lot, like double-digit percentages, within just six months. And we're talking about top-line metrics like activation, so it was just interesting, like, being able to have such impact very quickly at a company, and then the company itself went through all these milestones, you know? We started, you know, I mentioned I joined at 15 million, the next thing you know it's 100. You know, and things keep doubling, going through a public offering. So there's just so many stories that are unique to hypergrowth.

    7. LR

      You also didn't

  4. 9:0312:05

    Black Product Managers Network and Codepath.org

    1. LR

      mention in your background all these kind of extracurricular activities that you have. I've always been impressed with how much time you put into things that are kind of just volunteer projects on the side. Can you talk about some of the stuff that you do outside of your actual day job?

    2. JW

      Outside of my work at YouTube now, and also my family and two young kids, I'm also involved with two nonprofits that I co-founded. Both of them are actually in- in- about improving diversity in tech, which is just something I'm really passionate about. The first one is called Code Path and it's improving diversity for software engineers, and the second one is Black PMs, focused on product management. So with Code Path specifically, what we do is we train over 5,000 students every year at universities, typically in- university with strong underrepresented populations, and we help them find internships and jobs at top tech companies. And then with Black PMs, we have a community of over 1,000 PMs and aspiring PMs, and then we help them find community and also, uh, grow their skills. So both of them are nonprofits that I wasn't actually setting out to build them.

    3. LR

      (laughs)

    4. JW

      It's more like I had the need myself or I wish I had that, those sort of, uh, support when I was, uh, earlier in my career, and then I started helping folks and then one thing led to the other, especially with my co-founders, and then these became big.

    5. LR

      Sounds like a classic startup story. You solve your own problem and turns into-

    6. JW

      Yeah.

    7. LR

      ... a larger and larger thing. I think you know I try to work with Black PMs as much as I can, and I know that you recently had a conference, which was so cool. It was, I don't know, it was, like, a really big conference that you organized. I don't know how (laughs) y'all had time for all that. But anything you can share about this conference, and is there another one coming?

    8. JW

      So now we have a- an act- a really good team at Black PMs. The CEO, Brittany Bankson, and her team, Beni and Safo and others, have helped put together that amazing conference that I was able to, to attend. And it's amazing in that it's hard for underrepresented communities to see themselves, you know, in podcasts, at conferences, as speakers, you know, that sort of thing. So it gave that opportunity and it also enables us to realize that you're not alone, because part of why I created Black PMs, uh, with my co-founders is... Actually, I'll tell you the story. I think it was around 2016. I was at a barbecue. I met another Black PM, Marianna Quigles. I didn't know her and I was like, "Oh, you're a Black PM at Facebook. How many of you are there at the company?" You know? And we're joking and we're like, "Hey, I bet we can list all the Black PMs we know." And we had basically roughly 15 between the two of us and we're like, "Hey, let's bring them all together in a room and then to have community," and then from there started helping each other and that grew from 15 to now over 1,000.

    9. LR

      Wow. Amazing. It's really inspiring, the, the work that you do. I don't know how you find time for all this. I love that you found ways to kind of delegate this and have other people run the-

    10. JW

      Yeah.

    11. LR

      ... the program now. So...

    12. JW

      Yeah. So now I'm mostly on the board of these organizations.

    13. LR

      Mm-hmm.

    14. JW

      They have really solid teams for both Black PMs and Code Path and the teams are just, like, really amazing.

    15. LR

      This touches on the stuff that I want

  5. 12:0514:48

    The most important skills to refine as a PM: IQ skills and EQ skills

    1. LR

      to spend most of our time on in our chat, which is around...... mentorship and just generally becoming a stronger product manager through all the, through all the ways you can become a stronger product manager. You mentioned you had a lot of great mentors. I've heard from other people you've been a great mentor to them, and you've also just been really successful at a number of really world-class companies. And so what I wanna s- chat about is just what have you found to be the most important skills to develop as a PM, as you advance in your career, and then how to actually build those skills, partly with mentorship, partly other ways. And so maybe just to start, what have you found to be the most important skills in your career that have most helped you advance in your career and other PMs around you?

    2. JW

      In terms of skills, I think of it in terms of two buckets. One are IQ skills, intellectual skills, like what sometimes people call hard skills. And then the other things are the EQ skills, like s- oftentimes called soft skills. And what I've s- seen in my career is that early on I leaned more into the hard skills, you know, the IQ stuff. That was what was most helpful to me. And then later on, I, I spent more time getting better at the EQ skills. And the reality with PMs is that within each of these buckets there are so many skills and then you can feel overwhelmed. So my advice is really just, like, start skill by skill. So what I did specifically is, you know, I joined Slack, I was an ICPM. So when you join a new company, especially if you're, you know, like earlier to mid-career, you really wanna get good at things like execution, right? Like, IQ skills like execution, you know, product sense, strategy. So those were critical for me, you know, especially my first year at Slack. The other skill that I'll, I'll also call out, which nobody talks about for some reason, is interview skills. You know? Because so much of what gives you a chance to become better at a P- as a PM is working at a great company. (laughs) And how do you get that job beyond networking is actually becoming good at interviewing, you know? So if you think about my career, like getting into Slack changed my trajectory and I was able to do that because I got slightly somewhat good enough at, like, interviewing. I barely, barely got the job. And then I was really good at execution, you know, and, and got better at these other things, you know, product sense, strategy, et cetera. So in that, in that phase, you know, the things that I was working on, as I mentioned earlier, were things like improving new user activation. So it relies on those skills, identifying the opportunities, uh, running experiments, you know, executing quickly and so on. So that's the first set of skills.

  6. 14:4818:50

    How to improve your interview skills

    1. JW

    2. LR

      Before we move on, and the second set is EQ, right? Is that where you're going?

    3. JW

      Yeah.

    4. LR

      Cool. So maybe just one quick thread I wanna pull on is this interviewing skill. That's really interesting. Your point here is you're not... And I think you're gonna get to this, of just how to get better at these skills and you mentioned one of the best ways is to be surrounded by amazing people who can help you get better at these skills.

    5. JW

      Yeah.

    6. LR

      But you won't get there if you can't actually get into the company, like, a company like Slack. Is there something you've found to be useful in building these interview skills? And when you say interview, it's being interviewed, not interviewing other people, right? Like-

    7. JW

      Right. Yeah.

    8. LR

      ... passing these interview tests.

    9. JW

      Yeah.

    10. LR

      So yeah, I guess what have you found has been most helpful in helping you become a better interviewee?

    11. JW

      When people tell me, "Hey, I'm gonna interview at this company." First question I ask is, "How many mock interviews have you done?" And the answer typically is zero. It's, "Oh, I read the... A bunch of stuff, you know, I practiced in my head." But I'm like, "How many actual mock interviews have you done?" And I would recommend people to do dozens of, of those mock interviews. Now the other thing about practice is it's always better if you do deliberate practice. So if you mock interview with somebody who's actually good at interviewing, then you'll get better faster. But e- even if you don't do that, just going from zero mocks to practicing in your head to actually doing mocks with peers and others is gonna get you to a- to another level. And then the other thing I'll say is interviewing can be quite traumatic and difficult for a lot of people, you know, like even me, I mean, before I got this job, I had interviewed at Google I don't know how many times over the last decade or two.

    12. LR

      Wait, and so you're saying you interviewed at Google many times and you didn't get in and you kept looking for new opportunities?

    13. JW

      Yeah. Over, like, I, I graduated from MIT, you know, and I think even since internships times, you know, '07, I had interviewed for roles at Google and, and I didn't get those, uh, those roles.

    14. LR

      Oh, wow.

    15. JW

      Yeah. Or Meta or, or various other companies.

    16. LR

      Yeah.

    17. JW

      And it's because I wasn't good at interviewing and I didn't know people at those companies. And by the way, most things you do, people give you some feedback so you can get better at it. But interviewing, you never get any feedback.

    18. LR

      Right.

    19. JW

      And so that's the thing people don't talk about, but it's actually an important skill, uh, and... Or a barrier, you know, to underrepresented folks.

    20. LR

      To actually get feedback.

    21. JW

      Yeah. Y- you won't get feedback in the... After the interview at any company.

    22. LR

      That's a really good insight of just people see you join, like, a YouTuber, like, "Oh yeah, of course he's gonna get into YouTube." But you're saying that you actually tried to interview and get into Google many times and it took a number of attempts and advancing your career a little bit before you actually-

    23. JW

      Yeah.

    24. LR

      So don't, like... Don't feel so discouraged if it doesn't work out.

    25. JW

      Yeah.

    26. LR

      In terms of this mock, that's a really important point of just, like, actually doing the interviews, like, practicing, practicing, practicing. Not just, like, reading questions, but actually testing and practicing an interview. How do you... Like, if you're interviewing at a big company, there's a lot of videos out there of, like, "Here's the questions they ask, here's what they look for." And you're saying find people that work at the company and do these sorts of interviews with them. For companies that are smaller that maybe don't... Like, it's not as obvious what they're gonna ask you, do you have any advice on, like, how to find someone to do a mock interview with or how... Or what to actually be talking through?

    27. JW

      Yeah. It's harder at smaller companies. However, I think interviewing even at bigger companies will help you with the smaller companies.

    28. LR

      Mm.

    29. JW

      A lot of the times the bigger companies have more rigorous processes-... so if you can do well there then it's a bit easier elsewhere. But the key is really that practice part which people overlook.

    30. LR

      Cool. Well, maybe one last question then and we'll move on. Do you have any favorite resources or just advice of where to go find the questions to mock interview with, and then who do you look for to do these interviews with? Like just find someone at the company or one of these larger companies that you respect to, to mock interview with?

  7. 18:5020:39

    Why interviewing is more difficult for underrepresented people

    1. JW

      And then the last thing I'll say on this is interviewing is hard and especially I think hard for underrepresented folk because there's also like, it's high pressure, right? It's like high stress, high ambiguity.

    2. LR

      So much stress.

    3. JW

      Come into a company... I've gone into companies, like an interview and the whole panel, nobody looks like me. (laughs)

    4. LR

      Mm-hmm.

    5. JW

      I walk into the cafeteria, nobody looks like me, you know? And then you are interviewing and you have all this self-talk about like, "Hey, do I even wanna work there? Will I belong?" While you're trying to solve like complex problems, so that's also the other part companies don't think about. So what I, what I do with like, you know, folks like Black PMs that I coach is really help them find groups of people, like small groups. Let's say three of us, et cetera, three to five, and then you practice with that group who are going through the process. And because you like the people then it makes it a bit more fun and it also can help you prep for your own nerves in those interviews.

    6. LR

      So what I'm hearing is, and I know we hear this all the time, just if you're say a Black product manager, it's so much harder to not just get in 'cause there's pro- potentially bias at the company but you're just psychologically not feeling as comfortable 'cause like nobody looks like you. You're worried that they're gonna, they're gonna have bias against you. Is that what you find?

    7. JW

      Yeah, that- that has been my experience and it's also what I hear from a lot of people I mentor.

    8. LR

      And so your advice there, and this is helpful to a- anyone also, is just like practice even more because-

    9. JW

      Yeah.

    10. LR

      ... that's probably the best way to get over that as much as you can.

    11. JW

      Yeah, you wanna basically practice so much that even at your worst you're good enough, you know? And I've always felt like most interviews, like I literally did my worst. It's just that it was good enough to pass.

    12. LR

      Mm-hmm.

    13. JW

      You know, you're so stressed out, uh, you don't relate with the person, et cetera.

    14. LR

      Got it.

  8. 20:3922:44

    EQ skills: what are they and how to improve them

    1. LR

      Okay, so let's go back to the question I asked that I pushed us away from. So we were talking about what skills as a PM you wanna be focusing on that most-

    2. JW

      Yeah.

    3. LR

      ... help you in your career and we started with IQ and I just, I wrote a couple notes. So like there's the concrete skills, execution, product and strategy interviewing, and then there's a second bucket of EQ.

    4. JW

      So the IQ I already talked about, you know, those are the skills that helped me at, especially in my first year. It's like, you know, drive like pick good experiments, design good product experiences, and then drive results. But then what happened is as I get promoted, you know, manage people and then start having larger scope, then there's a lot of ambiguity and stress that comes in, you know, with that increase in scope and that's where like the EQ stuff shows up a lot. And specifically things like communications because it's no longer my team. It's like cross-functional partners, other teams, executives, so you have to communicate all the time to different people. And then the other thing is things like leadership. Now I'm driving initiatives that involve multiple teams, basic company level KRs. And then the other thing too is beyond leadership is just managing your team as well. Like how do you be a good manager? How do you deal with the ambiguity, stress? How do you influence various people? So these are the EQ, uh, skills and what I've seen is, number one, it's much harder to learn these skills than the IQ stuff. The IQ stuff is very intellectual. Sometimes you just need a mental model practice a bit. The EQ, I'm still learning these things. It's just like every, I'm trying to get better. And then the other thing beyond it being hard to learn is that the EQ stuff, it's what you need to focus on is specific to you. So you, Lenny, would... Ha- you probably work on something different than what I would work on versus if we're both trying to be better at strategy or execution, there's a lot more overlap. So there's a lot of self-awareness that you need to have to know even what to work on and then you need to continuously practice it.

  9. 22:4424:27

    The EQ skills Jules has had to develop over the course of his career

    1. JW

    2. LR

      What did you find was the most important EQ skill for your career that helped you in this journey?

    3. JW

      I don't know if there's one that single-handedly was the most important. I've had to develop on, on many of these things. So I can tell you for example, like communication is like something that is helpful, especially as you become more senior.

    4. LR

      Mm-hmm.

    5. JW

      And what happened for me is early in my career it was more about clarity and then conciseness and then later it became more about how do you tell a story and also like how do you communicate in an empathetic way? So specifically like you're telling the same story or presentation but to different audiences and each time you have to adjust it because, you know, the CEO will care about this part, the CFO will care about this other part and so on. So the- I think that's one area where I spent a lot of time and then the other thing also that has been helpful is the self-awareness part that I mentioned where it to- through mentorship, especially mentors who are very honest and helped me see my blind spots, I was able to see my own patterns, right? When I'm under stress, like for example, I tend to withdraw and not say anything so then you might think I'm disengaged. And by the way, like in an interview context you might be like, "Oh, does this person even wanna work here?" You know? So then once you know these patterns, you know, okay, I'm stressed right now but I need to say something so that people see that I'm, I'm actually interested in this problem, I'm just thinking through it. Or let me verbalize my thought process.... so that's me as an example. For you it, it might be the opposite. So the self-awareness piece has been really helpful and it's something I'm continuing to work on.

    6. LR

      That's an interesting

  10. 24:2726:09

    The importance of having a mentor or coach for self-reflection

    1. LR

      point that it's important to understand how you react and to figure out what's unique about you that you wanna be working on, especially within EQ. For this example you gave about how stress impacts you, how did you actually discover that? Was that this mentor just pointing out, "Hey Jules, I've noticed this happens," or is there anything else there that maybe folks would find useful?

    2. JW

      So generally, you need someone to put a mirror (laughs) in front of you-

    3. LR

      Mmm.

    4. JW

      ... figuratively, you know? So sometimes it's like you hire a coach, you know, they talk to you and they see patterns. I've done group coaching too. In this case specifically, it was a mentor, um, his name is Lorenz Dripsher. He was head of product at Pinterest, and became a mentor and now a close friend. And, you know, o- one day I was preparing for, I think, an interview or a presentation and he was like, "Hey, I've noticed that when you're thinking, you're just quiet, and he, let me tell you what's going on in my own head when I see that," and then he was like, "Hey, I'm telling myself that he's not interested in what we're doing." And I'm like, "Really? That's like the least thing," and then I realized that's a pattern I have, and over time through him and others, I've also observed other patterns.

    5. LR

      And I missed this, but was he a, a manager or just a mentor you had within the company?

    6. JW

      We didn't work at the same company.

    7. LR

      Mmm.

    8. JW

      Um, when I was at Slack he was head of product at Pinterest. Uh, we met at a, at a dinner and then from there, you know, he o- over time he became a mentor and then we started meeting and then when I would hit difficult situations sometimes I would call him and ask for advice and then through those interactions he's helped me identify some of my blind spots.

    9. LR

      Okay, awesome.

  11. 26:0930:13

    How cultivating self-awareness helped Jules improve his communication

    1. LR

      We're definitely gonna talk about mentorship and how to work with a mentor.

    2. JW

      Yeah.

    3. LR

      But let's kind of wrap up this EQ piece. So you mentioned with an EQ, skills to think about working on, communication, leadership, and management. Is there, is there anything else? And then is there an example of one of these skills and how, I don't know, it helped you in your career or it held you back until you figured out how to work on this?

    4. JW

      High level, I think those buckets, you know, are pretty broad, right? Comms, leadership, management. Within each of them there are various skills like, you know, setting vision, you know, strategy, like, listening to learn. Those sort of things. It's, it's actually the type of things that, uh, Matt Mochary talked about-

    5. LR

      Mmm.

    6. JW

      ... when he came to speak, um, at your podcast. So I mentioned communications was one thing, right? So what happened was when I was at Slack, you know, I was pretty good at, like, writing, which by the way, it was, I was terrible at, you know, a long time ago and it took me years, like, maybe decade to get better at, but then when it was time to present, I was fine at presenting but then if you ask me questions, things would crumble. (laughs) And that even happened to me once at an interview where I did well presenting and then they asked me a question and then I just gave an a- an answer that wasn't good. So then the self-awareness part helped me figure out what was going on, and for me specifically, I realized whenever people ask me questions, if I didn't know the answer, I would have like all this negative self-talk, and I basically would, you'd ask me a question and the question could be something like, "Why are we doing it this way?" Right? And it might come from a place of curiosity. You're just like, "Hey, I don't know. Can you tell me why? You have more context," right? But in my head I would hear, "I don't agree with this" (laughs) . You know? And that would be my self-talk, "Oh, this person doesn't agree with this," instead of being present and trying to understand where are they coming from and maybe asking follow-ups like, "Hey, thanks for asking the question. Like, is your concern more about, I don't know, scalability of this approach or is it more that you don't think it's effective even if it's not scalable?" You know what I mean? For someone else it might be the easiest thing, but for me, it took me, like, months and months to first of all figure out that I had this pattern and then once I figured out the pattern it was, it took also a while to now actually act on it so that now I'm comfortable if you ask me a question, sometimes I don't know and I'll say, "Hey, let me get back to you." Sometimes I don't know and I'll say, "Hey, I don't know, but here's what I'm thinking." This little thing that may seem so obvious to you took me a while and different people have different versions of these blockers.

    7. LR

      (instrumental music) This episode is brought to you by Linear. Let's be honest, the issue tracker that you're using today isn't very helpful. Why is that it always seems to be working against you instead of working for you? Why does it feel like such a chore to use? Well, Linear is different. It's incredibly fast, beautifully designed, and it comes with powerful workflows that streamline your entire product development process from issue tracking all the way to managing product roadmaps. Linear is designed for the way modern software teams work. What users love about Linear are the powerful keyboard shortcuts, efficient GitHub integrations, cycles that actually create progress, and built-in project updates that keep everyone in sync. In short, it just works. Linear is the default tool of choice among startups and it powers a wide range of large established companies such as Vercel, Retool, and Cash App. See for yourself why product teams describe using Linear as magical. Visit linear.app/lenny to try Linear free with your team and get 25% off when you upgrade. That's linear.app/lenny. I love these stories and this is a good segue to start talking a bit about not just what skills to focus on but how to actually get better at these things and identify these patterns in yourself. There's, like, a bunch of skills we just named, so let's also talk about where you think you start as a PM, as you're starting off as a PM, which skills to focus on first, second,

  12. 30:1335:32

    Strategies for learning new skills

    1. LR

      third. So let me just ask this broad question. We've talked about all these different skills PMs should have. What have you found to be most effective broadly at building these skills in your career?

    2. JW

      I will share my approach. It might not work for everyone. And later when we talk about, like, strengths and weaknesses, you might see why that works for me. So what I do specifically is when I'm trying to learn something new, I try to think about what is an outcome that I could drive? And if I drive this outcome, it would be proof that I'm better at this thing. So if we go back to this story of, like, when I joined Slack, I didn't know anything, literally anything about growth and I was telling myself, "I hope they don't fire me." But then the outcome I wanted is within six months, I wanted to shape enough experiments that were successful that drove activation by, let's say, X percent. So that's like very concrete. So then once I had this outcome, I worked backwards to figure out how am I gonna do that? So one of the things we, we can talk about later when we talk about strength is that for me, I'm really good at asking questions. So what I do then is I start asking questions like, okay, I'm trying to drive activation for Slack, what are some frameworks that I should use to drive activation? What are best practices? Like, what are examples? So I have a sense of the kind of question that if I were to answer them, I'd be able to drive the outcome. And then what I do is I read a little bit, not a lot, about the topic just to make sure I'm asking the right questions. So then I refine my questions and then I find the best people in the field and I just go talk to them. And that's where we'll talk later about the mentor part, the mentorship part. So in the case of activation at Slack, I was like, okay, what's the company (laughs) that define growth at the time, Facebook. What are the people that I can reach out to that do growth at Facebook? You know, and one of them was Bengali Kaba and also Adriel Frederick, who spoke at your podcast, and I had met both of them at a, at a random event. So then I'm like, I need to find a way (laughs) to have a chat with these folks and to help answer those questions with them, you know? So that's what I did with Bengali in particular, and also Adriel too, to a certain extent. I then learned, okay, here are frameworks to use for growth, for example, understand, identify, execute, spend a lot more of your time understanding why people aren't staying on Slack versus anything else. So then I had like pointers, and once I have the pointers, then I try to go do the thing. I'm like, okay, now let me... I call the user researcher, "Hey, can we do a research on, like, people who are signing up with Slack?" You know, data analyst, let's look at the data, what correlates with, uh, activation, you know, those sort of things. And then I, after I go through a loop where I actually see results, whether they're good or bad, I go back to the mentor and I'm like, "Hey, I did this. It was actually successful. Thanks a lot. Now I'm thinking about this other problem." (laughs)

    3. LR

      Hmm.

    4. JW

      You know, and I keep going and that's how it rings repeat. And over time I drive the outcome and I also know I'm getting better at this thing by, by working with the experts.

    5. LR

      There's a few interesting, uh, takeaways there. One is that you kind of create a forcing function for yourself to learn a thing. It's like, now I'm gonna learn this thing, let's create a goal that I, my ass is on the line to hit and then-

    6. JW

      Yeah.

    7. LR

      ...that's gonna force me to go figure this out.

    8. JW

      Mm-hmm.

    9. LR

      And then two, it's interesting how often you come back to mentors and other people around you helping you out, which is a really good reminder you don't have to figure things out for yourself. There's people out there that know these things and they're happy to help. A question I wanna ask, and I'll save this 'cause I, we're gonna talk about mentorship specifically a little bit later, is just like how to find these people. Not everyone has access to Bengali and Adriel, and I'm curious just how you found these folks, how you recommend other people find folks like that. But that's an awesome example. So one tactic you're talking about here is just work backwards from a forcing function you've created for yourself to learn a thing. And in this case, what was it you're trying to learn? You're trying to learn growth. Is that right?

    10. JW

      Yeah, I was trying to learn growth and I wanted to do it in a context of activation, you know, like new user onboarding and then later I also wanted to learn growth but in a different context, which was monetization. How do you drive revenue growth, you know, not get, not just get, like, more, uh, users. And then later it was things like how do I learn how to create a growth org? How do I structure my team? How do I set workstreams that add up to a coherent strategy? And you just keep going.

    11. LR

      In those examples, did you do the same thing, you found people to talk to?

    12. JW

      Yeah. Yeah. It's the same approach. And sometimes what happens is I have, uh, a few mentors that I just keep going to over the years and I just, it is just a topic exchange and sometimes I, I sort of get new mentors who are expert at these new topics. So it's a combination of those two things for me. And the thing is, you obviously can learn without this approach, but this approach makes you, at least for me, makes me learn so much faster.

    13. LR

      That's probably one of the most interesting things I've learned about mentors, and you're touching on this, that people wanna help. They're happy to help if people come ask, right? Unless they're just, like, dumb questions or they're just overwhelmed, people are generally very happy to help. People are always worried like, "Why would they spend any time trying to help me with this random thing?" It's,

  13. 35:3237:00

    Improving strategy, execution, and product sense

    1. LR

      it's usually the opposite. They're happy to help.

    2. JW

      Yeah, exactly.

    3. LR

      Coming back to the EQ and IQ buckets, are there other examples of ways you've learned to improve, say, like strategy execution, product sense, things like that?

    4. JW

      Whether you have a mentor or not, there's other things you, you kind of have to do. So for me, for example, one thing I do is I try to identify what's the best practice for something. So for example, let's say strategy, right? There was a phase where, you know, I got feedback, "Hey, you need to be better at strategy." You know? So then I'm like, "Okay, well, can you help me understand what are people you've had this company, you know..." That was like, you know, a while back, "Who you think have done a great job at strategy or what are examples of artifacts?" So then I see, I get these artifacts, you know, and I reverse engineering them, you know? So I, I try to think, okay, what are the to- the questions, the answer, maybe I'm answering all these questions.... how did they do it? And you start seeing the patterns, right? This person did it in a memo. This person did it in a deck. So it's not about the format, but, like, what is it, you know, about the... And then this person had a lot of data. This person is quantitative, qualitative. So that's a big part of what I do as well, where I... Whether it's... It's true for all these things, right? Like, so for execution it would be things like me attending another PM's meeting. "Oh, I heard this person is amazing at executing. Let me just see how they run a meeting," and then you're like, "Whoa." Things you didn't notice. Or

  14. 37:0040:22

    How identifying best practices can help you improve skills

    1. JW

      somebody is great at communicating and this... you know, and I'm like, "Okay. Well, they just sent this email. It's great. Let me save it." (laughs) I have like docs of like... where I save templates of things. And a lot of the, the reason I think people don't learn through osmosis that way is because one is, you're not at a company where you can see great artifacts sometimes. That's why I mentioned, like, if you can get a better company to do that. The other thing too is, even if you see the greatness around you, some people don't try to break it down to understand, why is this one great and not that one? So I actually do spend a lot of time every week reflecting like, "Oh, I saw these docs that were great, or I saw this presentation that this person gave." Like, I sometimes crash, like, presentations others, people, PMs give to, like, executives just to see how they handle, like, the questions or these sort of things. So a lot of it is just spending time observing as well.

    2. LR

      I love this advice. It's so powerful. Just like who is amazing at this skill and let me just go watch them and learn from them.

    3. JW

      Yeah.

    4. LR

      S- something that you touched on here is... and I talk about this a bunch, that one of the benefits of working at a large company like Google, like Slack, is that you have access to a ton of real examples of strategy documents and vision documents and roadmaps and things like that, that once you're out of a company, like me, nobody shares these things publicly-

    5. JW

      Yeah.

    6. LR

      ... 'cause they're sensitive. So one of the best benefits of working at a large company is they have access to real life strategy documents, vision documents, things like that. So you should really savor that and, and collect them, and to your point, just, like, study them. And I love your advice of just working backwards from like, "Okay, here's a strategy that worked. What is it about this strategy that I can use when I'm building my strategy? Like, what questions are they answering? How are they structuring it?" Things like that. So that's awesome.

    7. JW

      Yeah, and similar to the mentor point, people are actually happy to talk to you. They're even flattered because no one else asks them.

    8. LR

      Right, imagine. Yeah.

    9. JW

      So I'll reach out to somebody, I'm like, "Hey, I read your doc. Can we talk about it?" (laughs)

    10. LR

      Right. Whoever gets the... What PM ever gets someone coming to them, "I loved your strategy doc. Tell me all about it. I'd love to talk about that."

    11. JW

      Yeah. Yeah, and then the other thing I'll say too is a lot of learning happens through the iterations and not by seeing the final product. So, you know, we, we all see these products, right? Like the iPhone, like... Name your favorite product. But you don't know, like, what versions they tried and sort of eliminated, and that's the benefit you also get at a company that has great product management. So I actually sometimes tell the PM like, "Hey, don't just show me the one you just did. When are you gonna do your next strategy? Can I join you then? I just wanna sit and, like, watch you see... write down the outline and just understand your thought process." Or, "I wanna see when you're gonna write your next exec update and understand, like, wh- how are you going..." And you see them go through these iterations, you see them do things like get feedback that you didn't know they were getting all this feedback from. So seeing the, the backstage is also really helpful.

    12. LR

      It's interesting, and just as you're talking, I'm reflecting on how many benefits there are to working at a world class company. You are surrounded by really smart people who you can talk to and ask for advice and watch how they operate. You have access to really incredible documents and artifacts that you can learn from. Also, just the logo on your resume is really powerful for future job opportunities, which then comes back to the interview skills that you talked about and how

  15. 40:2242:38

    Communicating clearly and asking for feedback

    1. LR

      important it is to be good at that to get into a company like that.

    2. JW

      Yeah, totally.

    3. LR

      Interesting. Okay, what about on EQ? Any examples of how you learned some of those skills that you talked about, communication or leadership or management or anything along those lines?

    4. JW

      Yeah. So on the communication side, you know, I read some stuff like Mintos Pyramid Principles, like extremely helpful, and I know you had an article on that.

    5. LR

      Mm-hmm.

    6. JW

      I mention, uh, also that whenever I see a great email, exec update or whatever, I, I literally save it in this... in a special folder. (laughs)

    7. LR

      I love that.

    8. JW

      I also, by the way, I always ask for feedback more than I think many people, and I try to see patterns in feedback. So for me, you know, I, I... One thing I've observed is I tend to write long sentences, you know, coming from a fr- you know, Haitian, French background. But then I see that because I've seen enough feedback that are about it, so I see the patterns, you know? Or, as I mentioned earlier, I used to not be clear. Like, are you saying this solution or that solution? You know, like, it b- it's better sometimes to be wrong but clear, you know, than the oth- than the other way around. So that's, like, on the calm side, and then the other things is mostly for me through mentorship, like people like Lawrence, like, helping me be real with myself. Coaching, you know, I've, I've had a coach for a while, and I also do group coaching, which I really love. You know, right now I'm, I'm doing group coaching with a company called PathWise, uh, Leadership. Uh, so these sort of things have helped me sort of infer what my strengths and weaknesses are and then work on them. And then one thing I'll say also about the EQ, it was the most frustrating learning for me. You know, like, for the IQ stuff, within six months, sometimes three months, I can see, like, clear progress. Right? You see enough, like, documents, you know, you see five, six of them, (laughs) you start seeing like 80% of the patterns, right? But then with the EQ stuff, it's things I've been working on for years. You know, I am better at them, but I still feel I'm, I'm continuing to work on those things, and a lot of it is like... it's, you know, lifting weights or building muscles.... you know, you have to do it every day or every week. And if you stop doing it- (laughs)

    9. LR

      (laughs)

    10. JW

      ... over time, you, you atrophy again. So that's, uh,

  16. 42:3845:31

    Methods Jules uses to improve skills

    1. JW

      something that people need to acknowledge too. Like, give yourself time and then also learn these skills one at a time, ideally.

    2. LR

      Oh, interesting. Can you talk a bit more about that, learning skills one at a time? Is your approach just like, "Here's the thing I'm working on this, th- the next six months. I'm gonna focus on that."

    3. JW

      Yeah, so my approach is typically I'll say I'm giving myself, I don't know, three months, six months. It depends on what I'm, you know, what's the delta I wanna see in my behavior for this thing, and then I just go all in on that skill. So let's say I wanted to learn a strategy, right? So I'll be like, "Okay, I'm giving myself, let's say, six months. So every week I'm gonna do something related to learning strategy." I, it's gonna be maybe I read the strategy for another feature or product at my company and you just divide, right? Let's say there's 10 features or 20, it doesn't matter. You just do one a week, so 20 weeks. You see what I'm saying? And then the other thing is every week I'm also gonna practice it tor- towards my outcome. So I'm gonna spend, I don't know, three hours a week, maybe one hour a day, just thinking through my own product strategy and I do that for six months. So you do it enough that you get over the hump and then actually develop the skill. Now, the other approach you could take is, what most people do, is like they read, you know, an article from your newsletter or some other place and then like, "Oh, great. (laughs) I learned an insight." And then you go back to, you know, usual.

    4. LR

      And it's not like at the end of these six months you're done. "I'm strategy expert. I am good on strategy," right? It's just, it's your point, it's building this muscle that will never be fully built. It just will get stronger and every time you invest time learning something, it gets stronger.

    5. JW

      Yeah, exactly. So it's more that within six months you're clearly better. Now you can invest another six months to get to the next level. Or you could say, "Now I'm gonna switch focus to another skill and get that one to that, to a similar level."

    6. LR

      Is there a skill you're working on right now?

    7. JW

      Always working on something. Uh, one I can call out is listening. So one thing about the EQ stuff too, by the way, is you hear these words and depending on how familiar you are, you understand or don't understand what it actually means. So when I say listening, I'm good at seeking information to solve a problem. So if you come to me and you're like, "Hey Jules, I have this problem," I will know what to listen for and what to ask you. "Hey, Lenny, can you tell me A, B?" And then I'll help you solve the problem. However, there's also different listening patterns, one of which is you just create space for someone. It's not like you're seeking a particular information. Just give them space to tell you what they wanna tell you. And then the other side of it too is you help that person feel heard. You know, "Hey, I feel like you actually understand me and you've heard what I'm saying." So that's the part that I am working on.

    8. LR

      You mentioned the Matt Machari episode. I imagine you've been listening to that 'cause that has a lot of great advice.

    9. JW

      Yeah. Yeah, exactly. So it's those kinds of things, right?

  17. 45:3147:46

    How to approach asking for feedback

    1. JW

      And then he, he talked about like, you know, saying back to people like what you heard, you know, asking for more information, et cetera.

    2. LR

      Awesome. You mentioned that you ask for feedback from your peers, and I, I wrote that down. I wanted to double-click on that a little bit. How do you actually approach asking for feedback? Do you send like a survey? Do you just ask people in a meeting? How do you do that?

    3. JW

      The feedback piece, it's something that I had to get better at over time, like asking for it. Because what I realized is if people don't feel comfortable with you, they won't give you feedback because it's just, they're taking on a risk, right? Especially if it's constructive feedback. And by the way, that's also something that's hard about being underrepresented, right? People sometimes don't have the same natural level of connection with you. So I basically learned to go out of my way to make people comfortable giving me feedback. And there's different techniques and Machari also, Matt Machari also talks about some of them. Sometimes it's basically, you know, you ask in a very specific way, "Hey, I did this presentation. I'm working on, I don't know, having more executive presence. You know, did you feel that... To which extent did you feel that I showed executive presence?" So it's like a very specific thing, right? Versus, "Hey, how did it go?" So that's one thing you can do. Other thing you can do sometimes is you give yourself critical feedback in front of them and then you give them a chance to agree or disagree. (laughs) "Hey, I feel like this presentation didn't go well for this reason. Like, why do you think?" They're like, "Actually, I thought it went fine. (laughs) However, this other thing, you know, could have been better." And then the, the other thing I'll say that is very, very important if you're asking people for feedback is if you manage to get them to take the risk to give you the feedback, your answer has to be enthusiastically like grateful. That's the key. So what people knew at Slack, Google, et cetera, is like if you give me feedback, I'll be like, "Hey, thank you so much for like giving me. This is super helpful." Because people are like, "Oh, he actually likes the feedback." Now inside I'm, my heart might be melting, you know? I'm like, "Oh, I thought I got better at this." You know what I mean?

    4. LR

      Yeah.

    5. JW

      But externally I'm like, "Hey, thank you." And I mean it. And I think that's the key that most people don't sort of focus

  18. 47:4650:56

    Why it’s harder to get honest feedback on EQ skills

    1. JW

      on. And if you get more feedback, then you'll just get better at the things.

    2. LR

      That is such a good advice. All these very tactical ways of getting actual real feedback from people.

    3. JW

      Yeah. And then one thing I'll say too, by the way, it's harder to get feedback on the EQ stuff.

    4. LR

      Mm-hmm.

    5. JW

      And that's also why it's harder to develop and why a lot of people like reach like terminal levels in product because people are like, "Oh, they, they lack emotional intelligence." And they say that in calibration rooms, but not in your face. So that's also what you want when you hear feedback. You don't want just the like, "Hey, here's my fee- piece of feedback that I can prove." You also want the part that is like, "Here's how you make me feel or how you come across," that if this is taken out of context, it won't be good for... I don't want this to be shared publicly or taken out of context, but I want you to know. You know, and it could be things like, "Hey.When I talk to you, sometimes I feel like... I don't know, you're angry, you know? And then I'm like, "Oh, really? W- in what scenario?" And then it's like, oh, I was so focused then in listening to you intently that I can see now why I come across that way. But you could literally go your whole career and then nobody ever says these things, right? And that's the kind of feedback that I personally find most helpful is, like, the subjective feedback th- because nobody will tell me those things. And, you know, when somebody I trust tell me, then I'm like, "Oh..." Or like here's an example. I mentioned earlier I'm, I'm good at asking questions. I had somebody ask, like tell me, "Hey, sometimes when you ask questions, you sound more junior." And I was like, "Huh." And then I can see that because I asked the question, like plainly, like, "Hey, why did you do this?" Or, "How did you do that?" Instead of also saying, where I'm coming from, "Hey, I noticed this blah, blah, blah. Why blah..." You know what I'm saying? Instead of showing I have an understanding of the thing and then asking a follow-up question, I just ask the question bluntly without context, and people are, feel like, hey, I'm asking a very basic question. So that's the kind of feedback that I particularly value.

    6. LR

      The feedback you're getting is pretty incredible, like the stuff you shared about someone saying you come across as angry in a meeting if you ask questions or you sound junior. I don't know if I've ever gotten anyone to give me that brutally honest feedback. In those specific cases, what was it about these people that helped them give you this feedback? Is it what you talked about, you built trust with them over the years? Or is there something you did to get that kind of feedback?

    7. JW

      I mean, it's definitely they trusted me and they cared about me. So they trust that if they tell me the feedback without translating, that I would see the intent behind it. You know, and they were able to do that because, you know, after months and years of working together, they know how I respond to feedback. You know, because what happens is most people when you ask for your feedback, you kind of have to, like really do a lot of translation work so that it lands, you know, "Don't want to hurt your feeling, I don't want you to take this... "So they, I just told people, "You don't have to do that with me." So that's one, and then the other thing too is, people reciprocate also how you talk. Not, I'm not saying I talk to people like this, but I try to be vulnerable with people so they know with me they can be vulnerable, you know, and things are safe. Like, I really want to hear

  19. 50:5655:18

    The importance of understanding your strengths and weaknesses and leaning into the former

    1. JW

      things the way y- you experience it.

    2. LR

      Got it. So there's a lot of foundation-setting that you do to create this environment where people are like, "Jules, here's something that's going wrong. You can work on this."

    3. JW

      Yeah.

    4. LR

      That's an awesome takeaway. One other thread I wanted to pull on is, you mentioned focusing on strengths and how that ends up being really important. Something I'm a big believer in is focusing on strengths versus trying to make your weaknesses much, much stronger. Is there any advice you can share there about how to understand what your strengths are, why that's an approach to take in developing your skills?

    5. JW

      For the strength, um, breakthroughs for me, a lot of it was just talking with my mentor, Lawrence, Lawrence Ribeshire. And w- I organized this event for Black PMs at Pinterest where Lawrence was speaking, and then we were talking about, hey, what should he talk about, et cetera. And I don't know how, but in the conversation, he talked about doubling down on your strengths more than, you know, on fixing your weaknesses, and then he used me as an example. (laughs) And then the fun part is he had this approach of how you actually find your strengths. It's a very simple question where basically he's like, "Hey, what is something that a lot of people say you're good at, but you think is not a big deal?" You know, or it's not that important. And that's like the key. Or I should say, that's what resonated with me. I was like, "Oh, a lot of people keep saying I'm really good at networking." I'm like semi-introverted. (laughs) So I'm like, "Well, I don't know." Or how co- or Jules knows everyone. Or people will tell me, "Hey, you have, you ask great questions." And I'm like, "I ask basic questions." And then I, he helped me understand actually that's how you know it's a strength. Now, what you need to figure out is how do you get more out of that strength. An analogy, by the way, is imagine that you saw a fish and you were like, "Hey, you're really good at swimming." And then the fish would be like, "Oh. Duh, doesn't everybody swim?"

    6. LR

      (laughs)

    7. JW

      And so that's the key, and I invite people to think about that question, you know, like what's something people keep telling you you're good at but you yourself don't think is a big deal? You know, and that's how I was able to find a bunch of, like strengths for me. Like generally I'm thoughtful, you know, ask great questions. You know, I also like simplify problems a lot. I mean, we worked together on like product sense article, which is a very complex thing, you know, made it more simple. And then once you identify those strengths, then it helps to also think about why are you good at this thing? Because that's the underlying, like resource that you have. So a big part for me is I'm actually quite curious. And fun fact, I don't think of myself as curious, but people keep telling me I am, and even my mom was telling me when I was a kid, I used to like always like try to like unscrew toys to see how they work in the inside. So that's one thing, right? Like being curious, you know, helped me ask good questions and so on. And then the other thing too is once you have the strength, you want to understand the shadow side of it, and that's the connection between your strengths and weaknesses. So if we go back, and that was a key breakthrough for me, like especially Lawrence helped me understand that. So a strength and a weakness, it's not a binary thing. It's like the same thing, but it's a dial. In some contexts, it's like good, you know? In other contexts, it's, it's not good at serving you. So an example in my case is, you know, I've talked about I ask great questions, but sometimes if I ask a question without context, you know, I might come across as less knowledgeable, right? Or another thing for me is I'm able to take very complex problems and then create a mental model that's much simpler, you know, whether it's growth or other things. But until I come up with that mental model, if I'm in a meeting with you, I won't talk much about that topic.... I basically, I- I'm more quiet than other people when people wanna hear my point of view because I'm just listening and trying to create a mental model of the situation. So you're seeing how like the same strength is perceived as a weakness depending on context. So then once you have that, that is for me, I feel more empowered. I'm like, "Oh. I just have to dial it down a little bit here or dial it all a little bit here." And I also know this thing is serving me, which is why I keep doing the bad side of it.

    8. LR

      Awesome. This all often comes back to mentors in your life, and so I want to get to

  20. 55:1856:14

    Jules’s most impactful mentors

    1. LR

      talking about mentorship and how you find your mentors, how you work with them, all that kind of stuff, something we've been touching on a bunch and I'm excited to dig into. So maybe to start, can you just talk about some of the mentors you've had in your life, some of the most impactful mentors that you've had?

    2. JW

      I definitely had a large number of mentors over the years. Fun fact, when I came to the area eight years ago, I didn't know anyone. (laughs)

    3. LR

      Hmm. Wow.

    4. JW

      So it did take a while to sort of build those relationships. So I talked earlier about Ben Gallacaba who sort of helped me figure out how to grow Slack even though he wasn't working at Slack but helped me have the frameworks. I talked about Lawrence Ripscher, you know, he helped me discover my strengths and also like how to lean into them. Aaron Tighe is another friend and mentor who brought me to Google actually. And there's also Bradley Horowitz, former VP of Google Photos, also helped me in terms of like, you know, how do you think about leadership,

  21. 56:141:02:15

    The qualities to look for in a good mentor and how to approach them

    1. JW

      uh, and so on. The- and many other folks like Nikhil Singal, you know, VP at Meta, helped me with my PM career. So lots of mentors for sure.

    2. LR

      Okay, that's a killer list. Two questions.

    3. JW

      Yeah.

    4. LR

      One, what do you look for in a mentor when you're trying to find someone to work with? And then two, just like how do you actually find these people? Like most people listening are like, "Wow, I would love an amazing mentor to help me in my career. I don't know how to find one."

    5. JW

      Yeah.

    6. LR

      What advice do you have for folks finding a mentor?

    7. JW

      What I look for are two things. One is, are you good at one specific thing I'm trying to get better at? And then two is, are you good at explaining it? You know, and those two are, at least for me, they're important. I know people who are really good at their roles, at- at their job and at the subject but they- they don't actually know how to do it, or they- they don't really want to explain or- or cannot explain easily. So that's what I look for. And then in terms of where I find these people, it's really everywhere, right? (laughs) You know, if you look at the list I mentioned earlier, right? So Ben Galli, I met at an event. Like Facebook had a recruiting event, I showed up, I see this guy, I'm like, "Oh. Hi." You know, chat a little bit. I talked about Lawrence who's now a close friend, I met Lawrence at a dinner, he organized a dinner for under-represented PMs, we chatted, one thing led to the other and then he became a mentor and friend. Bradley, it was at a fundraiser. So, and Nikhil it was an intro via email, like somebody was like, "Oh, you should meet Nikhil." So I know this sounds counterintuitive. I don't think the hard part is where to find them. It's more about finding the right person and then how do you get a foot in? Now, what I've seen, like a lot of people sometimes they get mentors who are too senior or who don't actually think about the topic they're interested in. The- maybe they did five years ago, but once you find the right person, the key is like how do you have that initial conversation, like how do you s- get the- the foot in the door? And what I've found is, you should make the smallest ask possible, which is the opposite of what 95% of people do. 95% of people it's like, "Hey, I've never met you but I heard your talk or I saw you on LinkedIn or whatever, can we set up a call?" That's like a big ask. So what I do, like for example, there's this person who came to Slack, was a, he was head of product, you know, of a major company and then he gave a talk about different methods to like, improve products, like and he had this concept of like finding the heat for products. You know, he spoke at the company, I got his email, and I reached out, you know, in the evening and I was like, "Hey, thanks so much for speaking today. You talked about finding the heat for products. Is there an example of product that you think was created with this approach?" Like something he could answer in literally like two minutes via email. That was my question. It wasn't like, "Hey, you talked, now I feel entitled to like meet with you." But then the key is, once you get that foot in the door, like it could be a quick email, a tweet, a quick chat at an event, that sort of thing, and you get some advice that's useful. The key is to circle back with them at a later point and show that you've actually made good use of the advice. I think that's the thing nobody does. So what I would do, like for example, there's, um, currently the CEO of a top tech company, met at an event, she spoke there, and then she gave some advice that was useful. I emailed her like a quick follow-up type thing and then she gave me advice about how to rethink the mission statement for my nonprofit, all this via email. So then at some point I was like, "Hey, I've applied your problem trend competency framework to crafting the mission for my nonprofit. Here's what, where we landed." Replies back, and then what I would do then later is like maybe a month later, two months, X months later, I can reach out again for another

    8. NA

      (laughs)

    9. JW

      ... prompt and maybe I could say, "Hey this time it's a little bit more nuanced. Can we grab 15 minutes?" And the person was like, "Yeah, sure." That person was very, very busy but was like, "Hey, let's- let's do it." And then over time, you know, become Facebook friends, you know, that sort of thing. But that's the approach I take.

    10. LR

      That is such good advice. It reminds me of Tim Ferriss's advice also which is just like, don't go up to someone and be like, "Will you be my mentor?" Everyone's gonna be like, "I don't have time for that." Instead it's, to your point, it's the exact opposite. Just start, like, asking simple questions, right? And then over time build up a relationship and then over time maybe you start meeting regularly, but don't start, don't start big, start small.

    11. JW

      ... yeah, as small as possible.

    12. LR

      It's not like you just have one mentor. You've listed a whole bunch of people that have helped you over your career. It's not like, "Here's the person, they have to be perfect." Sounds like you kind of identify, "Here's a skill or an area I wanna focus and this person is gonna be really good at that."

    13. JW

      Yeah.

    14. LR

      And then I also just love the point about, like, it feels really hard to find an amazing mentor. And from what I'm hearing, the main thing you do is just go to things. Attend events, go to... Basically go events, meet people, right? That's kind of the foundation of what you're sharing is just meet as many people as you can. And amongst that group you'll find people that are probably gonna be helpful.

    15. JW

      Yeah. Uh, and I understand it can be harder for some folks. I mean, now I have two young kids, so (laughs) I don't do as many events. You know, I've also met quite a few people through introductions. Sometimes even cold outreach.

    16. LR

      Hm.

    17. JW

      You know, I had a chat with Shishir through cold outreach where-

    18. LR

      Oh, wow. Cool.

    19. JW

      ... I just asked, like, a very clear question and then he offered to come to Black PMs and share some insights, you know. Those kinds of things happen too. But you have to show the person that you're gonna make really good use of their time. So it'd be, you have to give really specific context. Not like, "Hey, let's grab coffee." It's like, "Hey, here's a very specific question. Can you share some thoughts or pointers via email?" And then they might offer, "Hey, why don't we just talk?" That sort of thing too. Yeah.

    20. LR

      That works really well. Anytime I get an email request of, "Hey, could we do a 15-minute Zoom or a coffee chat?"

  22. 1:02:151:06:51

    How to foster the best relationship with your mentor

    1. LR

      and I quickly do not have time for that, but an actual question that I can be really helpful with really quickly, that's so much easier. So that makes a lot of sense. The next thing I wanted to ask you is how do you build and continue this relationship? And then once you actually start engaging regularly, what do you suggest folks talk about in these, in these meetings if they're ongoing?

    2. JW

      I make sure to bring something very specific that I'm dealing with where they can provide input. A- and this is the opposite of what many people do, where they're like, "Hey, can you tell me about how you," you know, whatever it be, "your, your path to PM?" Which may or may not be relevant to them. Versus, "Hey, I've interviewed for three companies. I'm trying to decide among those three. You know, can I walk you through my thought process and get your feedback," right? So it's, it's very different. So I b- definitely make sure I, um, I bring a very specific context. And sometime it could be, I mentioned the example of Bengali, right? Like, "Hey, I'm now Growth PM at Slack. I'm trying to improve activation. Can I talk to you about how you approach growth in general?" You know, or it could be, "Hey, I'm having..." Like internal, like let's say I have internal mentors at Google, right? And I have a few. Then it's like, "Hey, I'm about to have this negotiation with this team. Can I walk you through my thought process and, and, and hear your advice?" So it's like very specific things. And then the other thing I'll say too is that when I talk to mentors, I always take notes. Like I mean, I'm seeing here, even here in this interview, right, you're taking notes. These are like-

    3. LR

      Absolutely.

    4. JW

      ... basic things people don't actually think about it som- sometimes. And then when I follow up, whether it's via email or in person, I bring up, like, older conversations. Like, "Hey, remember last time we talked about X? I did it." Or, "Hey, how's your daughter? I know she was going to college, you know, this semester. Like, how'd that go?" You know? So I always, like... It always feels like a continuation of a conversation and it feels like an actual relationship instead of transactional, uh, interactions. And then the other thing too is I try really hard to identify ways that I can be helpful. Sometimes at the end of chat I'll be like, "Hey, is there anything I can help you with? You know, anything top of mind for you." You know, and sometimes the person could be like senior or wealthy, it doesn't matter, and they're like, "Actually, yes, I'd love to better understand how the team is really doing. Nobody will tell me the truth." Or, "Hey, I am trying to hire for this role. You have this community of Black PMs. Like, do you mind sharing?" There's always, like, ways you can help, but most people are so, like, focused on themselves that they d- they miss out on these opportunities.

    5. LR

      The point about coming back to the person and sharing what impact their advice had and how it went is so good. Because, to your point, if it just feels like you're sharing all this advice and it just isn't going anywhere, and the note-taking, such great stuff. This is really good advice and I, I could see how it would work on me if someone's asking me for advice, so. (laughs)

    6. JW

      By the way, I mean, we didn't know each other, like, two years ago, right?

    7. LR

      Yeah. That's right.

    8. JW

      Yeah. So it's like a similar process where, you know, we got to know each other mostly via email.

    9. LR

      Yeah.

    10. JW

      And then one thing led to the other, right? And w- we try to help each other.

    11. LR

      And look at us now.

    12. JW

      (laughs)

    13. LR

      Any, uh, final thoughts before we wrap up and head to our very exciting lightning round?

    14. JW

      I have found the process of learning how to be a PM very difficult, and I also find it quite rewarding. You know, and I, I want to set expectation, especially for people who are earlier in, in their career. People may be frustrated by the process because you have all these skills, right? We listed, I don't know, half a dozen, a dozen that you're, you, you wanna get better at. So be patient. And then also, like, it takes a while to see massive differences but once you see those differences, you set yourself apart from your peers. So that's one thing. And then the other thing too is, it's really like building muscles. Like more so for the EQ stuff, but even for the IQ stuff, you know? It's, it... You have to practice. It's not just like read, you know, Lenny's, you know, top 10 articles for like two hours and then you're good. It's like read them, do what they say.

    15. LR

      (laughs)

    16. JW

      Get feedback on, y- after you do what they say and see like, "Huh, it worked for me. It didn't work for me." Re-read them again, find mentors, you know, et cetera. So it's a long process and I don't think people have that mental model around how to learn in general, but also specifically on how to learn the PM skills.

    17. LR

      And I imagine there's also this like one step forward, two steps back experience that often happens too, right? Where you're just like, "Oh, I thought I figured out how to think about strategy and then, shit, this one failed." And you're like, "Oh,

  23. 1:06:511:10:26

    Lightning round

    1. LR

      that was useless." No, this is how you learn. You fail sometimes. Oftentimes it works out.

    2. JW

      Exactly.

    3. LR

      Slowly but surely you move forward.

    4. JW

      Yeah, totally.

    5. LR

      Amazing. Well, with that we have reached our very exciting lightning round. Since we've gone a little long, I'm gonna keep it just four questions. I'm just gonna go through 'em pretty fast. Whatever comes to mind, fire off. Are you ready?

    6. JW

      Yeah.

    7. LR

      What are two or three books that you've recommended most to other people?

    8. JW

      One of them is Never Split the Difference by Chris Voss. Uh, it's about negotiations. And there's actually also a master class on-

    9. LR

      I was just gonna say that. I watched that. That was really good.

    10. JW

      Yeah. Yeah. And then another one is Connect by Carol Robin. It's inspired by, uh, Stanford's Touchy-Feely class, if you ever heard of it.

    11. LR

      Yeah, she did a guest post for the newsletter, actually.

    12. JW

      Oh, really? Awesome. Yeah, so and it's really an- helpful, especially as you're thinking about the EQ skills and how to improve your relationships with people.

    13. LR

      Awesome. I highly recommend that book. I haven't read it, but I read a lot of things about the class, and my friends have been in that class. And she wrote this guest post, and so, uh, that's, that sounds like a really good pick for EQ, so I'm actually gonna re-pick it up. Next question. Favorite other podcast that isn't this podcast.

    14. JW

      Lex Fridman is one that I'll call out. Um, brings really interesting speakers, and also, like on diverse topics, so I found it really helpful.

    15. LR

      Awesome. I also love that podcast. Favorite recent movie or TV show?

    16. JW

      I watch fewer (laughs) now. Um, so Top Gun: Maverick is a movie I really like. Uh, I'm sure many people have seen it, and for me it's like just like going back in the '80s. And then TV show is Never Have I Ever. So it's coming of age, uh, in America, uh, Indian teenager. Pretty funny and also deep.

    17. LR

      Awesome. I haven't heard of that one. Will check it out. Final question. Favorite interview question that you like to ask folks when you're interviewing them?

    18. JW

      One I used to ask a lot is, "What's something work-related that you're trying to get better at?" And I might... Sometimes I change the, the wording of it, but, uh, a big part of it is trying to understand how self-aware people are, to which extent they have a growth mindset, and then also, like how honest and vulnerable they can be. What I will say though about interview questions, by the way, is I don't anchor a lot on the first question. What I find the most value from are the follow-ups, you know? So yeah. So once you ask that question, you can take it in various directions, right? Like why did you focus on this versus other things? How did this come to your attention? Was it feedback you sought or feedback people ca- gave you, et cetera? Yeah.

    19. LR

      Awesome advice. Jules, this interview was a long time coming. It was everything I hoped it would be and more. Thank you, again, so much for being here. Two final questions. Where can folks find you online if they wanna reach out and learn more? And how can listeners be useful to you?

    20. JW

      So in terms of finding me, um, Twitter is one place, uh, to start. So my handle is julsdewalt, at. And then in terms of how people can be useful, it's really about paying it forward, and then sharing this with others, especially any parts that people find useful.

    21. LR

      Amazing. Jules, thank you so much. We'll chat again soon.

    22. JW

      Yeah. Thanks for having me.

    23. NA

      (instrumental music)

    24. LR

      Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

Episode duration: 1:10:26

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