Deb Caulet: Essential Leadership Skills for the Age of AI

About this episode

Caitlin Schiller interviews Deborah Caulet about essential leadership skills in the age of AI, focusing on the transition from individual contributor to manager and the challenges that come with it.

What happens in the gap between updating your LinkedIn title and actually knowing how to do the job? Caitlin sits down with Deborah Caulet—leadership coach, former VP of People at Blinkist, and someone who's spent 15 years helping leaders figure out what they're doing (and why they feel like they aren't doing it right!). Deb works with first-time managers and founders at growing startups, coaching them through the messy, humbling transition from high-performing individual contributor to someone whose job is to make other people shine. It's an identity shift, she says—and your sense of self has to catch up. They get into the classic traps: the leader who becomes their own bottleneck because delegating feels slower than just doing it, the difficult conversation that gets avoided for weeks because the anticipation is worse than the thing itself, and the imposter syndrome that 85% of professionals have felt at some point. Deb shares her CLEAR framework for navigating hard feedback conversations, and there's a thread about what it actually means to be kind versus nice at work — and why the difference matters more than you'd think. There's also a moment about AI's role in leadership…

People in this episode

Host: Caitlin Schiller

Guest: Deborah Caulet

Topics covered

• leadership
• AI
• coaching
• imposter syndrome
• management
• feedback

Keywords

• leadership skills
• AI in leadership
• coaching
• first-time managers
• imposter syndrome
• feedback conversations
• delegation

Mentioned in this episode

Organizations: Blinkist

Books & works: Work Rules!

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