Why Good People Become Bad Bosses | Jaime Woolf Artwork

The Best Boss - Presented by Diane Scott

What truly defines "The Best Boss"? Join Diane Scott as she delves into the heart of exceptional leadership in this insightful podcast series. Each episode features powerful stories and expert insights that uncover the qualities of transformative bosses who prioritize their people above all else. With over 20 years of experience as an executive coach to some of the world's foremost leaders, Diane brings a unique blend of professional wisdom and personal encounters.

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The Best Boss - Presented by Diane Scott

Why Good People Become Bad Bosses | Jaime Woolf

May 07, 2025 • Diane Scott

What causes good people to become bad bosses? In this thought-provoking episode, Diane Scott welcomes Jamie Woolf, former Director of Culture at Pixar and current CEO of Creativity Partners.

Jamie shares how leaders can unintentionally drift into negative patterns due to what she calls “power blindness.” Drawing on decades of coaching experience and her work at Pixar, Jamie unpacks how self-awareness, curiosity, and consistent feedback are essential to keeping leadership on course.

If you’ve ever wondered why leadership can get lonely at the top—or how to ensure you’re staying true to your values—this episode offers honest, practical guidance.

Topics Covered:

How power distorts perception and weakens feedback loops
Simple ways to build a trust map and seek real input
What Jamie learned from Ed Catmull and Pixar’s creative culture
Her own best boss story—and what made it unforgettable

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