In Part 2, Waverly Deutsch opens up about her decades at Chicago Booth, where she helped founders refine not just their business models but their ability to lead. She discusses how emotional connection strengthens logic, why confident delivery isn’t enough, and how AI is changing but not replacing human insight. 

For Gen Xers mentoring across generations or rethinking their own leadership, this episode is a reminder: great guidance begins with deep listening.

>>Coaching Across the Confidence Spectrum

“Some people came in over-confident. Some barely made eye contact.”

She explains how coaching required tailoring—not templating—entrepreneurs’ thinking.

>>Why Love Belongs in Leadership

“If you can’t connect with your idea, why should anyone else?”

Waverly talks about the human element most founders overlook when presenting.

>>Building Trust Across Generations

“EMBAs bring wisdom. Undergrads bring fire.”

She shares the challenge—and joy—of coaching both seasoned execs and young dreamers.

>>Relearning Her Own Leadership

“Coaching taught me how much I still had to unlearn.”

She reflects on what working with thousands of students revealed about her own blind spots.

>>AI Is Here—Now What?

“AI can write your pitch. But can it build your conviction?”

She discusses how tech is changing communication—and why human trust still drives every great pitch.

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Host: Vince Chan | Guest: Waverly Deutsch

--Chief Change Officer--
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