Have you ever worked for someone who started off inspiring, only to slowly lose their way? In this episode of *The Best Boss Podcast*, I’m joined by Jamie Woolf, former Director of Culture at Pixar and the co-founder of Creativity Partners, who explores why even the most well-intentioned leaders sometimes fall short.
Jamie’s perspective is unique. Her years at Pixar gave her a front-row seat to one of the world’s most creative environments, and yet, even there, she saw what happens when leaders become insulated by power. She describes how success can quietly create a culture of favoritism, ego, and comfort, unless intentionally disrupted.
This disruption was her role at Pixar. Brought in to shake things up, she witnessed how leaders, even those with brilliant minds and big hearts, can fall prey to what she calls “power blindness.” The slow erosion of self-awareness occurs when people stop giving you honest feedback and start laughing at your jokes just because of your title.
But this episode isn’t about villainizing leadership. It’s about understanding how to stay human and aware in a position of power.
Jamie offers a candid look into her own moments of missteps—times she prioritized efficiency over empathy or failed to recognize the impact her position had on those around her. Her vulnerability is refreshing, and her insights are invaluable.
One of the most powerful moments in the episode is when Jamie shares the story behind her TEDx Talk, *Why Good People Become Bad Bosses*. Initially written as a critique of toxic leadership, Jamie realized the deeper message was more personal: we all have the capacity to drift into bad boss territory unless we remain vigilant.
She shares practical advice for staying grounded: observe who’s talking in meetings and who isn’t. Ask for feedback, and don’t be afraid when it stings. Regularly get out of your office and into conversations with people who challenge your perspective. Most importantly, build what Jamie calls a “trust map”—a mental check-in of who you’re regularly engaging with, promoting, and relying on for input.
Jamie also reflects on her best boss, Katherine Sarafian, Senior Vice President of Talent Strategy at Pixar, who made her feel smarter, more confident, and more capable every time they met. This powerful reminder that the best leaders amplify others rather than diminish them is a powerful one.
This episode is an invitation for every leader to reflect. Are you still creating space for others to speak up? Are you seeing things clearly, or through the distorted lens of hierarchy? And if you’re unsure, Jamie shows us how to find out.
💬 And as always, I want to hear from you. What’s one word or sentence that made *your* boss the BEST BOSS?
👉 Share it here: https://dianescottinc.com/best-boss-stories/
Leadership is a journey, not a destination. And Jamie Woolf reminds us that the best bosses are the ones who stay curious, courageous, and deeply connected to their people.
