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Published · transcript-backed

Lenny Rachitsky: uncertainty

1 Mar 2026 Lenny's Podcast The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude)

“Another, I don't know, ritual and way of running teams that I heard about you, is you encourage team members roasting each other, which on the surface doesn't sound like a wonderful environment, but on the other hand, I hear constantly that the teams that you've built are just the happiest, the highest performing teams.”

— Lenny Rachitsky

Source trail

Everything needed to verify it.

Speaker
Lenny Rachitsky
Attribution
Verified speaker
Claim type
uncertainty
Recorded
1 Mar 2026
Publisher
Lenny's Podcast

Transcript context

…Yeah. And I think it's what makes your style of leadership stand out, or feel special to a certain person. Amazing. Another, I don't know, ritual and way of running teams that I heard about you, is you encourage team members roasting each other, which on the surface doesn't sound like a wonderful environment, but on the other hand, I hear constantly that the teams that you've built are just the happiest, the highest performing teams. Talk about, I guess, this idea of roasting and encouraging that, and just what you've learned about building awesome teams. Yeah, I think it's not that I'm like, "Yo, you should roast each other." I'm not forcing it in that way or anything, but when I think about the psychological safety, and teams and people that just get along with each other, when you think about your friends, you're always willing to push the boundaries a little bit and roast them. You're roasting your friends a lot, but you actually might not be roasting your coworkers a lot, because it's all just about comfort and safety. So it's not that I'm like, "Oh, I want my teams to roast each other." But I think it can be a really good sign when the people on your team feel comfortable just poking fun at each other a little bit. And I think that also can be a good sign when folks also feel the same way about you as a leader, where it's like there's just an element of they don't fear you as much, and they feel like there's a sense of safety where if they say something, they're not going to get fired. So an example of this is, with my last team, I feel like they would make fun of things that I would say at crits sometimes, certain phrases I would say.…

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