The Leadership Habit Why Good Humans Become Bad Bosses with Jamie Woolf
What causes a well-intentioned, capable leader to become the kind of boss that leaves employees feeling disengaged or demoralized? That’s the central question of this episode of The Leadership Habit podcast. Host Jenn DeWall sits down with Jamie Woolf—CEO of Creativity Partners and former Director of Culture at Pixar Animation Studios—to explore the concept of power blindness and the common derailers that turn good humans into bad bosses.
Whether you’re in a leadership role or aspiring to be, this episode offers an honest and compassionate look at how power, pressure, and blind spots can undermine the very qualities that make someone a strong leader. The good news? With self-awareness and reflection, these behaviors can be corrected.
Meet Jamie Woolf, CEO of Creativity Partners
Jamie Woolf brings more than 30 years of experience in organizational behavior and workplace culture. As the first Director of Culture at Pixar, she helped shape environments that nurtured creativity and trust. Through her consultancy, Creativity Partners, Jamie has worked with Google, DreamWorks, Gilead, and other major organizations to develop leaders who elevate teams through clarity, emotional intelligence, and humanity. Her work focuses on bringing more respect, trust, and authenticity into the workplace, starting with understanding your own influence as a leader.
Why Good People Become “Bad” Bosses
Many “bad boss” behaviors don’t stem from malice but from stress, blind spots, or outdated mental models of leadership. Jamie introduces the idea of power blindness—when leaders forget what it feels like to be on the receiving end of their authority. A simple behavior, like canceling a one-on-one meeting or sending late-night emails, can unintentionally signal disrespect or unrealistic expectations.
Recognizing Leadership Derailers
Even well-meaning leaders have derailers—traits that show up under stress and negatively impact their teams. Using the Hogan Assessment as a framework, Jamie explains how a strength like enthusiasm can morph into over-intensity, or how cautiousness can become paralysis. Leaders must learn to recognize when their “strengths in overdrive” are doing harm.
Feedback: A Leadership Superpower
Feedback can be hard to hear, especially when it challenges how we see ourselves. But as Jamie Woolf reminds us, it’s one of the most important tools a leader has to grow. “It’s our ego—we humans have fragile egos,” she says. “So just take a beat and let your physiology settle. Even the word feedback can trigger a physical reaction.”
Instead of jumping into defensiveness, Jamie recommends slowing down and getting curious. She offers a practical tip: ask yourself, “Where is maybe 5% of truth in this, even if 95% I might disagree with?” That mindset shift allows leaders to stay open without immediately dismissing what’s being said.
Jenn also notes that many leaders hear the same feedback over and over but still act surprised. “It’s wild,” she says. “You likely heard a variation of that feedback from your spouse, your boss, your child—but we still pretend it’s new.”
Jamie adds, “That’s because our strengths, when overused, become our shadow sides. Passion becomes intensity. Caution becomes paralysis. Feedback helps us recognize those patterns—if we’re willing to hear it.”
How to Increase Self-Awareness
Self-awareness isn’t a one-time realization—it’s a daily practice. Jamie encourages leaders to ask reflective questions often, such as:
- “Have people disagreed with me recently?”
- “Am I talking more than listening in meetings?”
- “How is my stress showing up in my body, and is it rippling out to my team?”
These aren’t just hypothetical questions—they’re a self-check for power blindness.
“Just knowing that by virtue of your title, people are treating you differently is a game-changer,” Jamie says. “If your team meetings are too harmonious or too courteous, that’s a red flag. People may not feel safe enough to tell the truth.”
Before any meeting, she recommends taking a moment to pause and ask yourself, “What’s my intention? How do I want to show up?” That simple practice can help leaders act with more clarity, humility, and openness.
Repairing Leadership Mistakes
Even the best leaders have bad days, but what separates a great boss from a bad one is what they do next. According to Jamie, it starts with accountability.
“Say you got too defensive or shut someone down,” she says. “You don’t just say, ‘Sorry, I was having a bad day.’ You reach out and say, ‘Here’s how I showed up. I’ve been thinking about what you said. Here’s the gem I found in your feedback, and here’s what I’m going to do differently.”
That kind of repair is what builds real trust over time. “Self-blame is still ego-driven,” she explains. “It’s not about beating yourself up. It’s about recognizing the gap between your intention and your behavior—and then course correcting.”
Jenn sums it up simply: “We all show up as less ideal versions of ourselves. Every single person you’ve encountered does. But growth starts when we admit it and choose to lead better.”
Where to Find More From Jamie Woolf
Want to explore Jamie’s work and resources in more depth? Here’s where to connect:
Coming soon: Download the Power Blindness Assessment and watch Jamie’s TED Talk on the same topic.
Want to Become a Better Boss?
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