Deep Questions, Steelmanning, and Building Reciprocity

A Note from James

I’m really concerned about the level of discourse in this country. It’s almost a cliché to say that now, but especially after the Charlie Kirk assassination, the division feels overwhelming. I even got invited to speak at the Oxford Union—the most prestigious debate society in the world—but ultimately declined because I didn’t like how the whole situation was being handled.

I can’t stand when anyone celebrates a death. Regardless of politics, it disturbs me. And every day, my social media feed is filled with more division and hatred. So I wanted to talk with Charles Duhigg. He wrote Super Communicators (now out in paperback) about how to actually connect with people in a world that seems torn apart. Even in a short conversation, I learned so much from him—things that made me think in new ways.

Episode Description

Pulitzer Prize-winning journalist and bestselling author Charles Duhigg (Super Communicators, The Power of Habit) joins James to explore how we can talk to each other in an age of polarization. From tragic political violence to everyday disagreements with family and friends, Charles explains why humans are wired for connection, how to ask better questions, and what it takes to turn conflict into understanding.

This episode is a practical guide to becoming a better communicator—especially when the stakes are high.

What You’ll Learn

• The three types of conversations—emotional, practical, and social—and why mismatched conversations cause breakdowns.
• How to ask “deep questions” that uncover values and experiences, not just surface facts.
• Why mirroring, looping, and listening carefully make people feel truly heard.
• How to handle anger and cliches with curiosity instead of combat.
• Why disagreements don’t destroy democracy—bad communication does.

Timestamped Chapters

• [03:08] James on division, Oxford Union, and why he turned down an invitation
• [06:06] Why James brought Charles Duhigg on the podcast
• [07:00] Political violence, polarization, and clashing conversations
• [10:42] What made Charlie Kirk an effective communicator
• [12:21] Communication as connection, not just information
• [13:21] Do both sides have to want connection?
• [15:20] Congress, partisanship, and performative politics
• [19:36] How “deep questions” build trust and reveal values
• [21:10] James on why he podcasts—and Charles’s analysis
• [23:39] Social reciprocity and feeling closer through vulnerability
• [24:23] History shows the value of disagreement done right
• [26:00] Why we reward bad behavior—and how to stop
• [27:09] James on gun control neutrality and frustration
• [29:00] Parenting lessons applied to political disagreements
• [30:00] “When you’re furious, get curious”
• [31:53] Moving past cliches by asking about personal experiences
• [33:08] Admitting confidence levels in arguments
• [34:19] Is Charles optimistic about America’s communication future?
• [34:50] A challenge for listeners: ask someone you disagree with “why does this matter to you?”
• [36:09] Closing thoughts: Super Communicators now in paperback

Additional Resources

• 📖 Super Communicators by Charles Duhigg
• 📖 The Power of Habit by Charles Duhigg
• 🌐 Charles Duhigg’s website

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