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Are you using AI to fail faster? Daniel Pink weighs in

Matt Henry
MH

Matt Henry

Chief Executive Officer

Matt Henry is Chief Executive Officer of Chatham Financial. He leads the firm’s global platform at the intersection of capital markets expertise and technology, helping clients navigate complex financial decisions with greater clarity and precision.

Summary

Judgment, decision quality, and trusted advice. For centuries, these have been uniquely human qualities and skill sets. Is that still true in the age of AI? To explore this question, I reached out to Daniel Pink, author of seven New York Times best-sellers. He was up for the discussion. Over the course of an hour, Dan and I tackle 16 big questions about AI, work, leadership, and the forces making human connection more valuable than ever.

Watch the full episode here.

This conversation covers: 

  • Why AI may make people work harder before it makes work easier – and why using the technology to reimagine new processes, not save costs, is the wisest path forward.

  • The questions every leader should ask about purpose, differentiation, and whether their work or “leading industry solution” would truly be missed if it ceased to exist.

  • How to build a career (and even a business) that complements machine intelligence instead of competing with it.

  • What superintelligence in the hands of... well, everyone, reveals about independence, core capabilities, the specialization of skills, and the shifting role of institutions.

  • How to solve the growing “apprenticeship gap” – and how to get the most out of early-career talent.

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