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Lenny Rachitsky: preference

8 May 2025 Lenny's Podcast How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC)

“I love that you can ask these hard questions of Claude/ChatGPT, these questions that make you really scared could ask it what are the answers, and even not have to do the hard work and maybe get a better answer.”

— Lenny Rachitsky

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Everything needed to verify it.

Speaker
Lenny Rachitsky
Attribution
Verified speaker
Claim type
preference
Recorded
8 May 2025
Publisher
Lenny's Podcast

Transcript context

…Look, one of my colleagues in the coaching company, he has uploaded, he kept all of his journal entries, I think over 10 years journal entries from Evernote, and he uploaded that. I think he uses Claude, and he's asked Claude to highlight things. What am I not saying that I need to say? What am I saying that's not being heard? He's asked it to reflect back, and I think it's been incredibly helpful for him. I think the result is that he is a better coach, which is interesting, because the feeling is, well, does this replace it? I am finding, I'm using ChatGPT really as a writing and thinking partner in a way that I did not have before, and I'm still using my live real human writing buddies, which are really important to me. Where does this all end up? I had no idea. It is unsettling, it's uncanny, and it's also enlivening and exciting. Well put. I love that you can ask these hard questions of Claude/ChatGPT, these questions that make you really scared could ask it what are the answers, and even not have to do the hard work and maybe get a better answer. I doubt that that will give you the best answers. Well, what it might do, which I think would be wonderful, is it might give you more questions to ask yourself. I'm a huge fan of powerful questions and the answer I give to a question like what am I not saying that I need to say? That question, you can ask yourself that question every single day. The question of how have I been complicit in creating the conditions I say I don't want? You can ask yourself that question every single day. To take a step back, the subtitle of my first book is Leadership in the Art of Growing Up. The Art of Growing Up is a practice. It's not a scientific moment where one day you wake up and you're done. It's an ongoing practice of not continuous improvement, but continuous inquiry that can feel exhausting when you contemplate it, but enlivening when you live it.…

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