Wired for Change

Guardrails & Gold Mines: Leading Through Uncertainty with Intent


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Exploring AI, Adaptive Leadership, and the Power of Questions with Chris Shipley

What does it take to lead through continuous change—when even the roadmap is evolving?

In this episode of Wired for Change, I sit down with Chris Shipley, an accomplished author - most recently The Empathy Advantage: Leading the Empowered Workforce- and seasoned leader with over 30 years of experience at the intersection of technology, journalism and innovation - to reflect on the evolving demands of leadership in an AI-driven world.

We explore:

  • Why adaptive leadership and vulnerability matter now more than ever

  • The underestimated power of asking better questions

  • How provider-sponsored health plans are navigating AI transformation

  • What it means to move forward with intent, even when the path keeps shifting

  • How leaders can balance hope, honesty, and uncertainty

Recorded in-person in Dallas at the Health Plan Alliance AI Accelerator kickoff, this episode is rich with real-world insight, memorable metaphors, and the kind of candor that today’s transformation leaders are craving.

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#AIleadership #DigitalTransformation #HealthTech #AdaptiveLeadership #WiredForChange #ChrisShipley #AIinHealthcare #LeadershipDevelopment #OrganizationalChange

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Wired for ChangeBy Amy Yee