Lenny RachitskyHost of Lenny's Podcast | Author of Lenny's Newsletter

Bet Harder on the People Already Winning

26 Sept 2026 · 1 min

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In this excerpt from Lenny Rachitsky’s YouTube video “Bet Harder on the People Already Winning,” he discusses a controversial leadership approach. He describes deliberately loading his top‑performing team members with ever‑more responsibility and decision‑making until they begin to fail, while publicly defending them in front of executives. He admits he lacks a systematic method for helping average or lower‑performing employees improve, essentially allowing them to fail on their own. This reflects a belief that pushing strong people to their breaking point demonstrates confidence in them, but also reveals a personal shortfall in nurturing broader team growth.

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You like to spend time riding your best people into the ground versus improving the average people.
If you see somebody drowning, you want to save them. I did the opposite. If somebody is strong and crushing it, I'm just like handing them more and more rope to hang themselves with. And I'm pushing them as hard as possible, like to the, to the point of breaking. Because like, at the end of the day, like one of the biggest leadership principles for me is that the people on my team, I will always defend in public, like in front of execs and stuff like that. And so people who are making consistently good decisions, I just want to load them up with more decisions until I start to see them make bad ones. And I think I try and really show that I believe in people. And when I don't, yeah, maybe this is just a personal thing. I just don't have a really good mechanism for helping people improve. I essentially let them fail on their own, which could be, I think, probably pretty frustrating for me as a leader to work for and somewhat sad.