Evidence receipt / uncertainty
Published · transcript-backedHilary 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)
“You should do that. But again, it's like you do that as a PM, you might get a chance to do that, I don't know, a couple times a week, maybe, maybe less often than that.”
Source trail
Everything needed to verify it.
- Speaker
- Hilary Gridley
- Attribution
- Verified speaker
- Claim type
- uncertainty
- Recorded
- 15 Jun 2025
- Publisher
- Lenny's Podcast
Transcript context
…So we're going to link to this GPT that you're talking about that people can try it out. And once you see it you're like, "Holy shit, I should just be doing this all the time," because you just get so many reps as a product builder. And we were talking about a similar one with understanding engineering benchmarks. I don't have an engineering background, so this was really hard for me when I was moving into product, is just getting an instinct for what types of things tend to be easier or harder for engineering teams. And so we can have one similar that's saying, " Here's the scope that's being proposed. If you had to t-shirt size this, which one would you choose and why?" And you can say, "Oh, this sounds, small or whatever." And it'll say, "Oh actually these types of integrations tend to be complex for these reasons. So it's probably going to end up being more like a large." And it doesn't have enough context to really inform you in the way that your tech stack at your company is. Although I guess could build it and give it that information and then it would, that would be cool. You should do that. But again, it's like you do that as a PM, you might get a chance to do that, I don't know, a couple times a week, maybe, maybe less often than that. And when you have this little tool, you can do it infinity times. You can spend an afternoon doing it. And so again, both the speed of those loops and the number of those loops that you're able to get is just radically different with AI compared to just when they come up in the course of your job. I think this is extremely cool. We're going to link to it. People should definitely play with this. Okay, I'm going to take us to two corners, recurring segments, of the podcast and then I want to talk about WHOOP before we get to a very exciting lightning round. So this is a new segment I'm trying out, I'm going to call it Pivotal Corner. And here's the question, what's the most pivotal moment in your career?…
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