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Jules Walter (YouTube, Slack)05 January 2023

Leveraging mentors to uplevel your career

7Frameworks
15Insights

Frameworks in this episode

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 1

Hot Take54:00

Your Strength and Weakness Are the Same Dial

Jules reframes strengths and weaknesses as not binary but the same trait on a dial that serves you in some contexts and hurts you in others. His gift for asking questions can read as junior when asked out of context; his ability to simplify complex problems means he stays quiet in meetings until he's built the mental model, which looks disengaged. Seeing the shadow side empowers him to just dial it up or down instead of trying to eliminate it.

  • Strength and weakness aren't binary; they're the same thing on a dial
  • Same trait is good in one context, bad in another
  • Asking great questions can come across as less knowledgeable out of context
  • Simplifying means he's quiet building a mental model, which reads as disengaged
  • Knowing the shadow side lets you dial it up or down deliberately

So, a strength and a weakness is not a binary thing. It's like the same thing but it's a dial.

Jules Walter · 54:00
#strengths#self-awareness#eq#career

Explainer· 3

Explainer12:30

The Two Buckets of PM Skills: IQ vs EQ

Jules splits PM skills into two buckets: IQ skills (hard/intellectual skills like execution, product sense, strategy) and EQ skills (soft skills like communication, leadership, management). Early in his career he leaned on the IQ skills, and later invested more in the EQ side. He warns each bucket contains so many skills that PMs get overwhelmed, so the move is to improve one skill at a time.

  • IQ skills = hard/intellectual: execution, product sense, strategy, interviewing
  • EQ skills = soft: communication, leadership, management
  • Early career he leaned into IQ; later he shifted to EQ
  • Each bucket has many skills, which is overwhelming, so go skill by skill

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…

Jules Walter · 12:30

And what I've seen in my career is that early on I leaned more into the hard skills, you know, the IQ stuff. That was…

Jules Walter · 13:00
#career#product-management#skills#eq
Explainer46:30

How to Actually Get Honest Feedback

Jules shares tactical ways to draw out real feedback: ask a very specific question (e.g. how much executive presence did you feel I showed?), or give yourself critical feedback first and let them agree or disagree. The most important move is your reaction: if someone takes the risk to give you feedback, respond with enthusiastic gratitude, even while your ego is bruised inside, because that's what makes people keep giving it.

  • People withhold feedback because giving it, especially constructive, is a risk
  • Ask specific questions, e.g. 'to what extent did I show executive presence?'
  • Give yourself critical feedback first so they can agree or add to it
  • React with enthusiastic gratitude even if inside your heart is melting
  • Being visibly grateful is why colleagues kept giving him feedback

your answer has to be enthusiastically like grateful. That's the key.

Jules Walter · 47:00

So what people knew at Slack, Google, etc. is like if you give me feedback I'll be like, hey, thank you so much for like…

Jules Walter · 47:00
#feedback#eq#communication#career
Explainer52:00

Find Your Strengths With the 'Fish' Question

Jules credits his mentor Lawrence with a simple question for finding your strengths: what's something a lot of people say you're good at but you don't think is a big deal? The fact that it feels trivial to you is exactly the signal it's a real strength, like a fish that doesn't realize swimming is special. For Jules the answers were networking, asking great questions, and simplifying complex problems, each rooted in his underlying curiosity.

  • Strength-finding question: what do people say you're good at that you think isn't a big deal?
  • If it feels trivial to you, that's the tell it's a genuine strength
  • Fish analogy: the fish doesn't think swimming is impressive
  • His strengths: networking, asking great questions, simplifying complex problems
  • Then ask why you're good at it, e.g. underlying curiosity, to get more out of it

Hey, what is something that a lot of people say you're good at but you think it's not a big deal?

Jules Walter · 52:00

imagine like you saw a fish and you're like, "Hey, you're really good at swimming." And then the fish would be like, "Oh, duh, doesn't…

Jules Walter · 52:30
#strengths#self-awareness#career#mentorship

Story· 3

Story16:00

You Never Get Feedback From Interviews (He Failed Google for a Decade)

Jules points out that interviewing is uniquely hard because, unlike most skills, you never get feedback after an interview. He shares that despite graduating from MIT, he interviewed at Google, Meta and others repeatedly over a decade or two and kept getting rejected, largely because he wasn't good at interviewing and didn't know people inside. The lesson: people who see him at YouTube assume it was easy, but it took many attempts.

  • Interviewing gives you no feedback, unlike almost everything else you do
  • He interviewed at Google many times over a decade or two and was rejected
  • Also rejected by Meta and other companies; MIT degree didn't guarantee it
  • The barrier is worse for underrepresented folks who lack internal connections
  • Don't feel discouraged if it takes many tries and a career build-up first

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.

Jules Walter · 16:00

But interviewing, you never get any feedback.

Jules Walter · 16:30
#interviewing#career#rejection
Story18:30

Interviewing When Nobody in the Room Looks Like You

Jules describes the extra psychological load of interviewing as an underrepresented candidate: walking into a panel and a cafeteria where nobody looks like him while trying to solve complex problems and battling self-talk about whether he even belongs. His answer is to practice in small groups of three to five peers going through the process together, so the reps calm the nerves and even make it fun. The goal is to practice so much that your worst performance is still good enough to pass.

  • Interviews are high-pressure, high-stress, high-ambiguity, worse when nobody looks like you
  • Self-talk about belonging competes with actually solving the problem
  • Practice in small groups of three to five peers going through the process together
  • Liking the group makes prep more fun and settles your nerves
  • Practice enough that even at your worst, you're good enough to pass

I've gone into companies like an interview, and the whole panel, nobody looks like me. I walk into the cafeteria, nobody looks like me.

Jules Walter · 19:00

you want to basically practice so much that even at your worst, you're good enough.

Jules Walter · 20:00
#interviewing#diversity#career#confidence
Story24:30

The Mentor Who Held Up a Mirror to His Blind Spot

Jules explains that discovering your own EQ patterns usually requires someone else to hold up a mirror. His mentor Lawrence Ripsher (then head of product at Pinterest) once told him that when Jules goes quiet while thinking, Lawrence's internal read was that Jules wasn't interested in what they were doing. That revealed a pattern: under stress Jules withdraws, so others assume he's disengaged, which meant he had to learn to verbalize his thought process out loud.

  • You usually need someone to put a mirror in front of you to see EQ patterns
  • Sources of that mirror: a coach, group coaching, or an honest mentor
  • Lawrence Ripsher told Jules his silence read as disinterest
  • Under stress Jules withdraws and can seem disengaged, e.g. in interviews
  • Fix: verbalize your thought process so people see you're engaged

So generally you need someone to put a mirror in front of you figuratively.

Jules Walter · 24:30

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?

Jules Walter · 25:00
#mentorship#self-awareness#eq#feedback

Tool· 2

Tool1:07:00

Jules's Book Picks: Never Split the Difference and Connect

In the lightning round, Jules recommends two books he shares most often. Never Split the Difference by Chris Voss is about negotiation and also has a companion MasterClass. Connect by Carole Robin is inspired by Stanford's Touchy-Feely class and is especially helpful for building EQ skills and improving relationships with people.

  • Never Split the Difference by Chris Voss, on negotiation (also a MasterClass)
  • Connect by Carole Robin, inspired by Stanford's Touchy-Feely class
  • Connect is aimed at EQ skills and improving relationships

One of them is Never Split the Difference by Chris Voss.

Jules Walter · 1:07:00

And then, another one is Connect by Carole Robin.

Jules Walter · 1:07:00
#books#negotiation#eq#recommendations
Tool1:08:30

His Favorite Interview Question (and Why Follow-Ups Matter More)

Jules's go-to interview question is asking what work-related thing the candidate is trying to get better at, which reveals self-awareness, growth mindset, and how honest and vulnerable they can be. But he says he doesn't anchor much on the first question; the real value comes from the follow-ups, probing why they focused on that and how it came to their attention.

  • Favorite question: what's something work-related you're trying to get better at?
  • It surfaces self-awareness, growth mindset, honesty and vulnerability
  • He doesn't anchor on the first question; follow-ups carry the real value
  • Follow-ups probe why they chose it and how it came to their attention

One I used to ask a lot is, "What's something work-related that you're trying to get better at?"

Jules Walter · 1:08:30

I don't anchor a lot on the first question. What I find the most value from are the follow-ups.

Jules Walter · 1:09:00
#interviewing#hiring#questions#self-awareness

Takeaway· 6

Takeaway13:30

Interviewing Is the Skill Nobody Talks About

Jules argues that being good at getting interviewed is an underrated skill that gates access to great companies, which is where you actually build all your other skills. His single biggest tactic is doing dozens of real mock interviews rather than just reading questions or rehearsing in your head. Deliberate practice with someone skilled accelerates it, but even peer mocks beat mental prep.

  • Getting into a great company is what lets you build every other skill
  • First question he asks candidates: how many mock interviews have you done? Usually zero
  • Do dozens of real mock interviews, not just reading or rehearsing in your head
  • Deliberate practice with a skilled interviewer compounds faster
  • Practicing at bigger, more rigorous companies makes smaller-company interviews easier

The other skill that I'll I'll also call out, which nobody talks about for some reason, is interview skills.

Jules Walter · 13:30

And I would recommend people to do dozens of of those mock interviews.

Jules Walter · 15:30
#interviewing#career#skills
Takeaway30:30

Create a Forcing Function: Learn by Working Backwards From an Outcome

Jules's core learning method is to pick a concrete outcome that would prove he got better at a skill, then work backwards. When he joined Slack knowing nothing about growth, he set a target of shipping enough successful experiments to move activation by X% within six months. From that outcome he generated the questions he'd need to answer, read a little, found the best people in the field, and iterated with mentors, which he says makes him learn far faster.

  • Define an outcome that would be proof you improved at the skill
  • Example: move Slack activation by X% via successful experiments in 6 months
  • The outcome puts your ass on the line and forces you to figure it out
  • Work backwards into the questions you'd need to answer
  • Read a little, then find the best people and iterate with them

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…

Jules Walter · 30:30
#learning#growth#career#mentorship
Takeaway37:00

Reverse-Engineer the Great Work Around You

Jules learns skills like strategy and execution by collecting great artifacts (strategy memos, exec updates, emails) and reverse-engineering them: what questions do they answer, how are they structured, quantitative vs qualitative. He saves templates in a special folder and even sits in on other PMs' meetings and exec presentations. He stresses that a lot of learning comes from watching the iterations and backstage feedback, not just the polished final product.

  • Collect great artifacts and reverse-engineer what makes them work
  • Ask what top questions they answer and how they're structured, not the format
  • Save great emails and updates as templates in a dedicated folder
  • Sit in on other PMs' meetings and exec presentations to watch them handle questions
  • Learn from the iterations and backstage feedback, not just the final product
  • Reflect weekly on the good docs and presentations you saw

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…

Jules Walter · 37:30

a lot of learning happens through the iterations and not by seeing the final product.

Jules Walter · 39:00
#learning#strategy#career#product-management
Takeaway42:00

Learn One Skill at a Time, Like Building a Muscle

Jules recommends going all in on a single skill for a fixed window of three to six months rather than dabbling. For strategy, he'd read one other team's strategy each week and spend a few hours a week practicing his own, doing it enough to get over the hump. He frames EQ especially as muscle-building: it never fully completes, and if you stop practicing it atrophies, unlike the quick wins of IQ skills.

  • Go all in on one skill for a fixed 3-6 month window
  • Divide the learning: e.g. read one team's strategy per week for 20 weeks
  • Also practice toward your own outcome a few hours each week
  • Do it enough to get over the hump and actually develop the skill
  • EQ is like lifting weights: stop and it atrophies; the muscle never fully builds

and a lot of it is like it's you know, lifting weights or building muscles.

Jules Walter · 42:00

So you do it enough that you get over the hump and then actually develop the skill.

Jules Walter · 43:30
#learning#eq#discipline#career
Takeaway58:00

How to Land a Mentor: Make the Smallest Ask Possible

Jules says the hard part of mentorship isn't finding people (he met his via events, dinners, fundraisers and email intros) but getting a foot in the door with the right one. Instead of asking a stranger for a call, which 95% of people do, make the smallest ask possible, like a two-minute email question about a specific point from their talk. Then circle back later to show you actually used their advice, which almost nobody does, and only then ask for more time.

  • Finding mentors is easy via events, intros and cold email; getting a foot in is the hard part
  • 95% of people make a big ask (a call) with a stranger
  • Instead make the smallest ask possible, e.g. a 2-minute email question
  • Circle back later to show you used the advice, which nobody does
  • Only then escalate to a 15-minute chat; start small, not big

And what I found is you should make the smallest ask possible. Which is the opposite of what 95% of people do.

Jules Walter · 58:00

the key is to circle back with them at a later point and show that you've actually made good use of the advice.

Jules Walter · 59:00
#mentorship#networking#career
Takeaway1:02:30

How to Keep a Mentor Relationship Alive

Once a mentor relationship is going, Jules brings a very specific problem he's actually dealing with rather than vague questions like 'how did you become a PM.' He always takes notes and references older conversations and personal details so it feels like a continuing relationship, not a transaction. He also looks for ways to be genuinely helpful back, because even senior, wealthy people usually have something they need, and most people miss that.

  • Bring a specific live problem, not a generic 'tell me about your path' question
  • Always take notes during mentor conversations
  • Reference past conversations and personal details so it feels continuous, not transactional
  • Proactively ask how you can help; even senior people have needs
  • Most people are too focused on themselves to offer help back

I make sure to bring something very specific that I'm dealing with where they can provide input.

Jules Walter · 1:02:30

when I talk to mentors, I always take notes.

Jules Walter · 1:03:30
#mentorship#relationships#networking#career