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What happens when we bring more humanity—and humor—into technology, leadership, and the systems that shape our world? In this episode, discover how we can do good better amidst complexity, disruption, and AI-driven change.
In this episode, Kate O’Neill welcomes author, comic, and advisor Jess Pettitt to explore how imperfect people and organizations can “do good better.” Together, they tackle topics from confronting bias in technology and leadership, to creating cultures where dissent—and learning from failure—are possible. Jess Pettitt shares high-stakes humor and vulnerable stories, unpacking why “good enough now” is sometimes vital and sometimes not enough.
Topics covered:
- Using humor to open up difficult conversations
- The limits of certainty and performance in leadership
- Organizational values and aligning intention with action
- The power of curiosity and the “Prepare, Recognize, Respond” framework
- Navigating positional power and fostering inclusive cultures
- Exposing neutrality and hidden power in technology and policy
- Redefining hope, agency, and responsibility in complex environments
- Generosity and actionable steps for failing together in the right direction
Connect with Jess Pettitt
Website
Episode Chapters:
00:00 Introduction and Welcome
01:19 Guest Introduction: Jess Pettitt and Body of Work
03:19 A Flamingo, Complexity, and Unexpected Human Moments
05:21 Humor’s Role in Difficult Conversations
09:11 Learning, Language, and Avoiding Performative Efforts
12:16 Organizational Values, Shared Goals, and Truth Telling
15:24 Discomfort with Complexity and the Realities of Safety
17:00 Making Room for Dissent and Practicing Curiosity
19:41 Feedback Loops and Real-Time Adjustment
24:08 AI Tools, Accuracy, and Personal Responsibility
26:44 Cultural and Conscious Response vs. Habitual Reaction
29:42 “Good Enough Now”—Progress, Stakes, and Ethics
33:24 Humanity, Everyday Generosity, and Self-Reflection
36:30 Balancing Ego and Humility in Driving Change
39:09 Power, Voice, and Cultural Structures in Organizations
45:25 Recognizing Politics and Power Hiding Behind “Neutrality”
51:59 Imagining a Hopeful, Human-Centered Future
57:32 Reclaiming Coexistence and Forward-Looking Hope
01:01:29 Closing Remarks and Takeaways
