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Hilary Gridley: uncertainty

15 Jun 2025 Lenny's Podcast How to build a team that can “take a punch”: A playbook for building resilient, high-performing teams | Hilary Gridley (Head of Core Product, Whoop)

“I feel like I've had so many of those times where I don't know, when I was growing up, I felt so confident in how I felt about everything.”

— Hilary Gridley

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Everything needed to verify it.

Speaker
Hilary Gridley
Attribution
Verified speaker
Claim type
uncertainty
Recorded
15 Jun 2025
Publisher
Lenny's Podcast

Transcript context

…Maybe I'm wrong, maybe I could be wrong. Well, I mean that's what it is. I feel like I've had so many of those times where I don't know, when I was growing up, I felt so confident in how I felt about everything. And then you get out there and you're just like, "Oh, I was missing some things." And after a while you're kind of like, "Okay, maybe I should approach these situations a little differently with the possibility that maybe I'm missing something." So I actually asked your boss Kelvin, which is an awesome name by the way, Kelvin, about this moment. When I asked him what to ask you, and he brought this up actually, and here's the way, described it, "She may describe it as being thrown into the deep end or baptism by fire, but the reality is that she had the core skills and this was simply an opportunity for her to let those shine even more. She was an incredible first principles thinker, quick to tune the framing of problems as she learned more context. It's a great example of luck is what happens when preparation meets opportunity."…

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