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 PettittWebsiteEpisode Chapters:00:00 Introduction and Welcome01:19 Guest Introduction: Jess Pettitt and Body of Work03:19 A Flamingo, Complexity, and Unexpected Human Moments05:21 Humor’s Role in Difficult Conversations09:11 Learning, Language, and Avoiding Performative Efforts12:16 Organizational Values, Shared Goals, and Truth Telling15:24 Discomfort with Complexity and the Realities of Safety17:00 Making Room for Dissent and Practicing Curiosity19:41 Feedback Loops and Real-Time Adjustment24:08 AI Tools, Accuracy, and Personal Responsibility26:44 Cultural and Conscious Response vs. Habitual Reaction29:42 “Good Enough Now”—Progress, Stakes, and Ethics33:24 Humanity, Everyday Generosity, and Self-Reflection36:30 Balancing Ego and Humility in Driving Change39:09 Power, Voice, and Cultural Structures in Organizations45:25 Recognizing Politics and Power Hiding Behind “Neutrality”51:59 Imagining a Hopeful, Human-Centered Future57:32 Reclaiming Coexistence and Forward-Looking Hope01:01:29 Closing Remarks and Takeaways
