Jan 5, 2023 · 1h 10m · lennys-podcast
Leveraging mentors to uplevel your career | Jules Walter (YouTube, Slack)
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In this interview, product leader Jules Walter joins Lenny Rachitsky to share tactical frameworks for accelerating a product management career through deliberate skill acquisition, emotional intelligence, and proactive mentorship. Jules details actionable methods for identifying blind spots, soliciting candid feedback, deconstructing expert artifacts, and expanding diversity across the tech industry.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Lenny holds 29.3% of the talking time here. How this is scored →
Lenny as informed peer 4.0 Guest teaching 6.5 Guest disagreement 0.2 Lenny pushing back 0.3
speaking balance: gold is Lenny, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 57:45 Critiquing standard mentorship outreach approaches
Jules points out that 95% of people approach prospective mentors entirely backwards by making large, entitled demands on their time instead of tiny, respectful asks.
Hardest push from Lenny ▶ 20:38 Lenny redirecting conversation back to EQ skillsLenny explicitly pulls Jules back to the core agenda, reminding him that they need to explore the EQ skill bucket after diving deep into interviewing.
Biggest teaching moment ▶ 47:20 Masterclass on eliciting raw, honest feedbackJules educates Lenny on advanced psychological techniques to lower people's defensive barriers and invite brutally candid criticism by reacting with genuine outward gratitude.
Lenny holds their own ▶ 38:02 Lenny synthesizing the competitive advantage of big tech artifactsLenny synthesizes and articulates the unique institutional advantage of working at large tech firms where PMs have rare access to real-world strategy and roadmapping artifacts.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Lenny as informed peer | Guest teaching | Guest disagreement | Lenny pushing back | Why |
|---|---|---|---|---|---|---|
| Jules Walter's Background from Haiti to YouTube | 3 | 4 | 0 | 0 | Lenny opens with a warm welcome and prompts Jules to share his unique career trajectory from Haiti to YouTube. Jules walks through his background in medical devices, startups, Slack, and YouTube TV, setting a collaborative and friendly tone. | |
| Transitioning into PM and Driving Early Slack Growth | 4 | 5 | 1 | 1 | Lenny inquires about transitioning into product management and scaling growth at Slack. Jules gently clarifies that he was not the first PM at his initial startup before explaining how leaning on growth mentors helped him drive double-digit activation metrics. | |
| Co-Founding Nonprofits CodePath and Black Product Managers | 3 | 5 | 0 | 0 | Lenny highlights Jules's impressive volunteer work founding CodePath and Black Product Managers. Jules details how organic demand from underrepresented tech talent spurred the growth of both organizations from small meetups to thousands of members. | |
| Categorizing Product Management Skills into IQ and EQ | 4 | 6 | 0 | 1 | Lenny asks Jules to identify the most crucial skills for PM career advancement. Jules introduces his core framework dividing competencies into IQ skills (execution, product sense, strategy, interviewing) and EQ skills. | |
| Mastering Interviewing Skills and Overcoming Bias Barriers | 4 | 7 | 1 | 1 | Jules delivers an insightful masterclass on PM interviewing, highlighting how mock interviews and deliberate practice help overcome systemic biases and psychological pressure. Lenny validates the difficulty of interviewing at big tech firms. | |
| Developing EQ, Advanced Communication, and Strategic Leadership | 4 | 7 | 0 | 1 | Lenny steers the conversation toward EQ skills. Jules explains why EQ is vastly harder to master than IQ, requiring personalized self-awareness, tailored executive communication, and managing personal stress patterns. | |
| Uncovering Blind Spots and Stress Patterns with Mentors | 3 | 7 | 0 | 0 | Jules shares a candid personal story about learning through a mentor that his quiet thinking during meetings was perceived as disengagement or disagreement. Lenny explores how coaches and mentors act as mirrors for self-awareness. | |
| Sponsor Segment: Linear Modern Issue Tracking Software | 4 | 7 | 0 | 0 | After the sponsor read, Jules outlines his structured method for skill acquisition: creating an outcome-based forcing function, generating key questions, and consulting subject matter experts. | |
| Deconstructing Strategy Artifacts and Observing Expert PMs | 6 | 6 | 0 | 0 | Jules explains how reverse-engineering strategy docs and shadowing top PMs during draft iterations accelerates learning. Lenny reinforces this by emphasizing the hidden advantage of having access to real-world corporate artifacts at top tech companies. | |
| Building EQ Muscles, Iterative Practice, and Active Listening | 4 | 7 | 0 | 0 | Jules breaks down how he focuses on one specific skill for three to six months at a time, drawing parallels to lifting weights. He discusses his current focus on empathetic listening and creating space for colleagues. | |
| Practical Techniques for Eliciting Brutally Honest Feedback | 4 | 8 | 0 | 0 | Jules shares concrete tactics for soliciting raw, unvarnished feedback, such as offering self-critiques first and responding with enthusiastic gratitude. Lenny remarks on how rare it is to receive such brutally honest feedback. | |
| Identifying Core Strengths and Navigating Their Shadow Sides | 4 | 7 | 0 | 0 | Jules details a framework taught by Lawrence Ripsher for identifying strengths: looking for things others praise that feel trivially easy to oneself. He explains how every core strength has a corresponding shadow side that must be dialed appropriately. | |
| Finding Mentors and Crafting High-Impact Low-Friction Asks | 5 | 8 | 1 | 0 | Jules shares a contrarian insight on reaching out to mentors: start with the smallest possible, low-friction ask rather than requesting large blocks of time. Lenny relates this to Tim Ferriss's mentorship advice on building authentic rapport over time. | |
| Sustaining Meaningful Mentorships Through Continuity and Reciprocity | 4 | 7 | 0 | 0 | Jules explains how closing the loop by reporting back on how mentor advice was implemented solidifies long-term relationships and transforms transactional encounters into genuine friendships. | |
| Embracing the Non-Linear Product Management Learning Curve | 4 | 6 | 0 | 0 | Jules summarizes the non-linear, often frustrating nature of PM skill development and completes the lightning round with book recommendations, podcasts, and favorite interview prompts. |
Statements from this episode (23)
Walter: Slack revenue grew 10x from $50M during his tenure
“When I joined, revenue was around fifty million. When I left roughly four years ago, it was 10 extra.”
Walter: YouTube adding NFL Sunday Ticket to Primetime Channels in 2023
“We just recently announced that we, we're adding a NFL Sunday ticket in 20, 23 to primetime channels and also to YouTube TV.”
Walter: Breaking into PM relies primarily on startups or internal transitions
“It's really, really hard to get into product. 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, i…”
Walter: Early Slack mobile changes increased activation by double digits
“Within six months, I was able to ship changes in the news 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.”
Walter: Interviewing skills are critical for PM career growth via top companies
“The other skill that 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 as a PM is working at a great company. And how do you get that job beyond networking is…”
Walter repeatedly failed Google and Meta interviews before joining YouTube
“I had interviewed for roles at Google and I didn't get those roles. Yeah, or Meta or various other companies. And it's because I wasn't good at interviewing and I didn't know people at those companies.”
Walter: Tech interviewing is uniquely difficult because companies never provide feedback
“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.”
Walter: Practice PM interviews until your worst performance passes the bar
“You want to 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.”
Walter: EQ skills are harder for PMs to learn than IQ skills
“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 year I'm trying to get better. And th…”
Walter: Misinterpreting curious questions as disagreement impeded his early career
“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'd basically would, you'd ask me a question and question could be something like, why are we doing it this way? R…”
Rachitsky: Big tech's hidden perk is access to private strategy docs
“One of the best benefits of working in large companies, they have access to real life strategy documents, vision documents, things like that.”
Walter: PMs learn more from observing iterations than from finished products
“A lot of learning happens through the iterations and not by seeing the final product. So, you know, we all see these products, right? Like the iPhone and like name your favorite product. But you don't know like what versions they tried and sort of eliminated. …”
Walter: It is better to communicate clearly and be wrong than be ambiguous
“It's better sometimes to be wrong, but clear, you know, than the than the other way around.”
Walter: Emotional intelligence skills atrophy without continuous practice
“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 over time, you atrophy again.”
Walter: Responding with enthusiastic gratitude is critical when receiving constructive feedback
“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.”
Walter: Product managers plateau because peers withhold emotional intelligence feedback
“It's harder to get feedback on the EQ stuff. 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 like emotional intelligence. And they say that in calibration rooms, Bu…”
Walter: Core strengths are traits others praise that feel effortless
“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.”
Walter: Strengths and weaknesses are context-dependent dials of one trait
“So 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 not good.”
Walter: Pick mentors who excel at a specific skill and can explain it
“But I look for 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, at least for me, they're important. I know people who are really good at their roles, at…”
Walter: Initiate mentor outreach with the smallest possible ask, not a meeting
“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…”
Walter: Convert advice into mentorship by following up on results
“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 actu…”
Walter: Mentees should bring specific problems rather than generic career questions
“I make sure to bring something very specific that I'm dealing with where they can provide input. And this is the opposite of what many people do, where they're like, hey, can you tell me about how you know, whatever, your path to PM, which may or may not be re…”