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 that takes a surprising turn.

The conversation lands on a deceptively simple piece of advice for anyone staring down a new role and feeling the weight of everything they don't yet know. It's the kind of thing you'll want to remember on a Monday morning.

Resources
Deb's Rec: Work Rules! by Laszlo Bock 
Ben's Rec: Radical Candor by Kim Scott 
Caitlin's Rec: A.Q.: A New Kind of Intelligence for a World That's Always Changing by Liz Tran

Deborah Caulet's 7-Day Difficult Conversation Challenge (free) Deborah Caulet's 12-Week Leadership Bootcamp. 

Let us know what you thought of this episode! Find us on Instagram at @simplifypod. Subscribe to our newsletter on beehiiv here. Also, you can email us at info@kollomedia.com

This episode of Simplify was produced by Caitlin Schiller, Ben Schuman-Stoler, and engineered by João Lucas in Berlin, Germany, for Kollo Media.

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