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Lenny Rachitsky: 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 don't know, maybe you could keep it anonymous just to make this a little reel of the kind of mental model you might want to build around someone.”

— Lenny Rachitsky

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Everything needed to verify it.

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

Transcript context

…t, but I try to send my team just a quick rundown in Slack of, "Here are the most important conversations or the most interesting conversations I had this week. Here's what that person said verbatim." Again, I write a lot of notes so I've got it. If you've got a transcriber, maybe that'll help you. "And here's what I interpret that as. Here's why I think they say that. Here's where I think that's coming from and here's what I'm going to do differently as a result." And these aren't long. And sometimes if I don't have time, I'll just, in a team meeting, I'll literally just go through my notes from the week and sort of voiceover stuff and editorialize it as I go. And over time, I think my team has a pretty good sense of what people are saying and how to think about the thinking behind it and how this person thinks, how this person thinks and how I think. And I think when you get an entire organization working that way where everyone's working from the same models of what the CEO thinks matters, what level of risk tolerance the company has, things like that, then you can actually start to move much, much faster and communication becomes much, much, much less painful. So the tactic here is to help your teams kind of build a mental model of everyone in the company that matters so that it's... The way you put it almost is when they're emailing them or asking for something, they already know how they're going to respond. Is they're an example you could share of something like this, of just something a person at Whoop of how they think? I don't know, maybe you could keep it anonymous just to make this a little reel of the kind of mental model you might want to build around someone. So our CEO, Will, is somebody who obsesses over pixels in a way that is challenging to get things through design review, but I think results in a product that is a thousand times better than it would be if he were accepting of small excuses here and there for, "Oh, well this, we had to cut scope here. We couldn't quite do what they wanted here." He sets a high bar and he holds it and he doesn't compromise. And I think this can sometimes get misconstrued, and I think a lot of people might think that he just wants maximal scope on everything. And I think that is a misunderstanding of what he cares about. We often get feedback from him that's like, "This doesn't feel like the future and everything that we're building needs to feel like the future." A lot of people hear that and they're kind of like, "Oh gosh, we're never going to get this thing done on time. We can't make any sort of sacrifices to scope or anything like that." But when I hear that, what I hear is more that we have this AI coach in the product, we have all this amazing data in the product. We're tracking every single one of your heartbeats and we're pulling at all this other data and we have every screen is a moment to show that to people in a way that feels like something that has never existed before. And there are small ways to do that, right? It's like how you pull in. If you're explaining a concept like VO2 Max, which is a measure of your cardiovascular health, you can explain that to people with static content or you can explain that to people by bringing their data into the method of explanation that you're using. You can make it really conversational because you're using this AI coach. You can make it feel more like you're talking to a person and a person who by the way has all the data about you, which doesn't exist today. Your doctor doesn't have that, your coach doesn't have that. And that's not like, "Oh gosh, we've got to blow up the scope on this thing and make it a hundred X as big." But it's finding these little touches to say, "Wow, that was really magical, that was really thoughtful and this feels like the future. This feels like I'm very conscious of the fact that this product knows so much about me and is able to sort out the signal from the noise on that in these really small and elegant ways." And so for something like that, I would get that feedback in design review or I'd hear that in a design review and maybe one of my PMs would be in that design review. And so I bring that to the team. And I hear of things like that in a few different design reviews. So I bring those back to the team and I'm like, "I've noticed that recently we are consistently getting this type of feedback. Here's why I think it's really important to Will, because I think he's really focused on building the health company of the future. And I don't want you all to think that this just means we have to just throw AI at everything and we have to just throw maximum scope at everything.…

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