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Anthropic exec shares how she uses AI to help manage her team

Anthropic product executive Dianne Penn said on 'Lenny's Podcast' that the company's Claude AI model has helped her become a more effective manager, and she has shared her approach with fellow managers at Anthropic. Penn uses a custom Claude 'skill' inspired by the book 'Crucial Conversations' to prepare for workplace discussions, describing the AI as 'almost like individualized personalized coaching' that pushes back on her ideas rather than simply agreeing.

read2 min views1 publishedJul 27, 2026
Anthropic exec shares how she uses AI to help manage her team
Image: Businessinsider (auto-discovered)

Anthropic product executive Dianne Penn says artificial intelligence has become part of her management toolkit.

Penn said on an episode of "Lenny's Podcast" released Sunday that Anthropic's flagship AI model, Claude, has helped her to become a more effective manager and that she has shared her approach with fellow managers at the company.

"That's actually a thing that I've been sharing more with our managers, of okay, how do you actually use Claude to make you a better coach, because it's hard sometimes to find the right perfect words, and the models have a lot of perfect and right words," said Penn.

Penn, who has served as Anthropic's head of product management for research and labs since 2023, said she has encouraged team members to use AI to have "better conversations with each other" and "be better managers."

"I don't think it's necessarily just about raising the IQ of like experiences we build, but also I used it a lot and actually like prepping for how to have better conversations in the moment during like crucial conversations," she said.

Penn told podcast host Lenny Rachitsky that she loves the book, "Crucial Conversations: Tools for Talking When Stakes are High," and has created a custom Claude "skill" inspired by its lessons to help her prepare for certain workplace conversations.

"I actually have a skill that helps me figure out — am I going in the right level of detail given the situation at hand, and actually helping me be a better manager and better supporter for the team," she said.

Penn described her use of Claude in these scenarios as "almost like individualized personalized coaching."

"There are times where I end up not using suggestions from Claude. But it actually ends up being very helpful for just coming up and brainstorming — am I thinking about reactions in the right way? How do I actually go a bit deeper faster, build trust faster, be more direct?" Penn said.

Still, Penn said she doesn't rely on Claude to do her thinking for her. Instead, she uses it to refine ideas after first forming her own point of view.

Penn said AI shouldn't simply reinforce what a user already believes. Instead, she argued that it should function more as a "thinking partner."

"What you don't want is like an AI that just agrees with you," Penn said. "What you want is this technology to actually augment and grow and like get to a better outcome. And so sometimes it's having Claude push back makes me better."

"Like a co-worker, I want somebody to push back when my ideas are not fully formed," Penn said.

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