Evidence receipt / preference
Published · transcript-backedHilary Gridley: preference
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)
“When I think about any kind of habit I'm trying to build on my team, that's something that I'm always thinking about, is how can I make sure that when a person does this, they feel really great? And part of why I like Custom GPTs as a tool for helping people learn to use LLMs, and I talk about this on the podcast I did with Claire, on how I AI, is because if you put in the prompt, you as the person building the custom GPT, you write the prompt, you put it in, you design it such that somebody can upload a specific document.”
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Everything needed to verify it.
- Speaker
- Hilary Gridley
- Attribution
- Verified speaker
- Claim type
- preference
- Recorded
- 15 Jun 2025
- Publisher
- Lenny's Podcast
Transcript context
…Sweet. But basically, it's one little thing you can do every single day. And the key with this is, again, consistency. So you need to get people doing this thing every day, reducing friction. I think a mistake a lot of people make when they start thinking about how to drive adoption is, they're like, "Oh, we have to show people how to do their work with these tools." But I'm like, "Well, work is hard." And if you are on a deadline for something, you've got to get something done, the last thing that you ever want is more friction associated with getting it done. It is so annoying when you're trying to get a thing done, and your tools are being changed on you, and you don't know how the thing works, and the hot keys are all different, or whatever. So I actually think, using it in situations that have nothing to do with your work are way easier, because you're removing all of that friction of, "Oh wait, I got to go think about, 'All right, what's a project that I'm working on? Oh, I put this into ChatGPT, and I didn't really get a good answer.'" Or, "Now I'm frustrated, because this thing's taking longer than I need it to take, or whatever." I start with things that are just fun, simple use cases. It might be coming up with times to take a vacation, or places to go on vacation. Or it might be uploading your calendar into ChatGPT, and asking it for ideas, for talking points for the meetings, or things where the person doesn't have to think, because it's all just spelled out. And things where there's no external work pressure, that you have to apply this to, that's going to make it an unpleasant experience. So consistency, reduce friction. And then, most importantly, designing reward loops. And this is something, that when I'm talking to people about designing for behavior change, the number one thing I always tell them is, "You are not thinking enough about the reward loop." The reward loop needs to be powerful, it needs to be immediate, and it needs to be emotional, so that when this person does the thing that you want them to do, they feel like a million bucks. When I think about any kind of habit I'm trying to build on my team, that's something that I'm always thinking about, is how can I make sure that when a person does this, they feel really great? And part of why I like Custom GPTs as a tool for helping people learn to use LLMs, and I talk about this on the podcast I did with Claire, on how I AI, is because if you put in the prompt, you as the person building the custom GPT, you write the prompt, you put it in, you design it such that somebody can upload a specific document. And then, they can get a specific output, like feedback on that document, or maybe something more fun than feedback, an improved written version of that document. They get the joy of like, "Oh, this helps me. This was cool," without any of the despair of, "Oh, I'm not very good at prompting, and this didn't really work, and I'm frustrated." on of that document. They get the joy of like, "Oh, this helps me. This was cool," without any of the despair of, "Oh, I'm not very good at prompting, and this didn't really work, and I'm frustrated." And so, I just always think about that in general. If I'm trying to build any kind of habit on my team, it's less about the accountability of how I'm enforcing this, and more about how I make it so rewarding for people to do it, that they do it naturally.…
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