Doing Good Better

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