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Hilary Gridley: recommendation

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 have to give them things that take no more than a minute or two to do. And actually, I have a 30 days of GPT, I call it, of a list of 30 things to do, one every single day, that I don't know anyone who has gone through this, and not come out the other side, feeling a hundred times more confident in their skills, and actually using it every day as a habit, because it's built as a habit formation tool, and not an education tool.”

— Hilary Gridley

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

Transcript context

…Okay, cool. Yeah. Okay. So another habit/skill that you are really good at, that I've heard from folks is, and you've mentioned this a couple times, is just building habits, helping your team build good habits. And coming back to the CBT stuff, just like behavior loops and things like that. Talk about just what that is, why that's important, what you help your team learn there. Yeah, I'm obsessed with habit formation, and reward loops and behavior change, and all of these things. And when I think about trying to change behavior on your team, or just trying to encourage your team to do more of the behaviors that you believe are associated with success, I think a lot of people think about it more of an education model, where it's like, you teach the thing, you assess the thing, and then there's some accountability around the thing. And I think, if you think about it more in the context of behavioral psychology, it actually works a lot better. So I'll give you an example. Many leaders have been trying to think about how to drive AI adoption, AI upscaling on my team, and what that can look like. And when I talk to people about this outside of the company, I'm always surprised like, "Well, how do you measure it, and how do you enforce it?" And I don't really think about any of that stuff. I'm thinking about, "How am I creating habits around using this?" And for me, there's a couple of things there. So it's consistency. How are you getting someone doing something every single day? And to do that, it has to start small. It has to start super easy. You have to give them things that take no more than a minute or two to do. And actually, I have a 30 days of GPT, I call it, of a list of 30 things to do, one every single day, that I don't know anyone who has gone through this, and not come out the other side, feeling a hundred times more confident in their skills, and actually using it every day as a habit, because it's built as a habit formation tool, and not an education tool. And this is using a specific GPT build, or building their own GPT, or what's the habit there?…

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