
Anthropic product executive Dianne Penn says Claude helps her prepare for difficult conversations and coach direct reports, framing AI as a 'thinking partner' that pushes back.
Anthropic product executive Dianne Penn said she uses the company's flagship AI model, Claude, to prepare for difficult workplace conversations and coach her direct reports. Penn described the approach on an episode of "Lenny's Podcast" released Sunday, and said she has shared it with other managers at Anthropic.
"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," Penn said.
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. She built a custom Claude skill inspired by the book "Crucial Conversations: Tools for Talking When Stakes are High." The skill helps her assess whether she is going into the right level of detail for a given situation.
"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 framed the model as a "thinking partner" that should push back rather than just agree. She said she forms her own point of view first, then uses Claude to refine ideas and brainstorm reactions. The tool, she said, is "almost like individualized personalized coaching."
"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."
The use case highlights a shift in how AI is being applied in the workplace. Rather than automating tasks, Penn's approach focuses on augmenting managerial soft skills such as communication and coaching. That could broaden the addressable market for enterprise AI tools, which have largely focused on coding, customer service, and content generation.
Anthropic has positioned Claude as a safer, more steerable alternative to other large language models. Penn's emphasis on the model as a thinking partner, not a yes-man, aligns with that positioning. For companies considering AI adoption, the ability to tailor tools for specific human interactions may become a differentiator.
Penn said she does not rely on Claude to do her thinking for her. Instead, she uses it to stress-test her own ideas. "Like a co-worker, I want somebody to push back when my ideas are not fully formed," she said.
The episode is one of the first detailed public accounts of how a senior Anthropic executive uses the company's own product in day-to-day management. It suggests that even within AI firms, the technology is still finding its footing in interpersonal work.
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