Podcast Summary: People I (Mostly) Admire

Episode: How to Have Great Conversations (Update)
Date: September 20, 2025
Host: Steve Levitt
Guest: Charles Duhigg (journalist and author of Super Communicators and The Power of Habit)

Episode Overview

This encore episode revisits Steve Levitt’s candid conversation with Charles Duhigg, a Pulitzer Prize-winning journalist and acclaimed author, focusing on the science and art of great conversations—the subject of Duhigg’s book, Super Communicators: How to Unlock the Secret Language of Connection. Levitt, having applied Duhigg’s strategies himself, explores with Duhigg the often-misunderstood goals of communication, the value of “deep questions,” and practical tools for transforming how we connect with others—in personal, professional, and even fleeting everyday encounters.

Key Discussion Points & Insights

1. Why Great Conversations Matter

• Levitt’s Transformation: Through podcasting and reading Duhigg’s book, Steve Levitt comes to value conversation as a key life skill and is impressed by how "shockingly powerful" Duhigg’s tools are when put into practice.
  • “In the two weeks since I read Charles Duhigg's book, I've tried hard to put the book's ideas into practice and I have to say it has been shocking to me how powerful these tools are.” (02:04)

2. The Instincts and Traps of Conversation

• Natural Instincts: Duhigg asserts that conversation is rooted in instincts shaped by evolution, though often misapplied or misunderstood.

  • “You are a great conversationalist. You've literally spent your entire life practicing… once we understand how conversations work, we can converse and connect with, really, anyone.” (02:48–03:44)

• The Curse of the How-To Author: Levitt asks if writing about communication creates pressure on Duhigg to excel at it in all contexts; Duhigg humorously recounts his wife referencing his own book when critiquing his dinnertime monologues.

  • “My wife…will say, you know, there's this book about communication that I think you could read that would really help you a lot.” (02:48)

3. The Three Types of Conversation Goals

• Not All Conversations Are Alike: Duhigg introduces the distinction between practical, emotional, and social conversations, stressing the importance of matching your approach to the other person’s needs:

  • “Every discussion contains multiple conversations… practical, emotional, and social…If we're having a different kind of conversation than someone else, then we're probably failing to connect.” (06:09–07:37)

• Levitt’s Realization: Levitt realizes he'd long assumed all conversations sought solutions, missing the emotional or social needs of others, a common blind spot for logical, problem-solving types.

  • “For most of my life, I thought that the purpose of every meaningful conversation was to find a solution to a problem. But I was so wrong.” (05:51)

4. Deep Questions and Permission-Giving

• "Deep Questions": Duhigg explains that truly connecting involves asking questions about a person’s values or experiences, prompting them to reveal their authentic selves.

  • “You asked this barista something about her values…Those are deep questions because they're inviting the other person to reveal something about themselves.” (09:58)

• Levitt’s Experiment: Levitt describes engaging a barista in a meaningful conversation, noting how even small moments become “magic” when you engage emotionally rather than transactionally.

  • “It is so shocking to me. It's like magic. Watching people melt when you acknowledge a little bit of emotion.” (08:54)

• Permission and Empathy: Duhigg shares a teacher’s conversational tool: asking students “Do you want to be heard, helped, or hugged?” Matching the conversational type matters most.

  • “At the core of how we communicate is giving each other permission.” (13:17)

5. Overstepping Social Boundaries (and the Rewards)

• The Power of Vulnerability: Levitt gives examples of crossing typical conversational boundaries—asking children of divorce how they feel, or talking openly about his own son's death—often resulting in relief and gratitude.

  • “To talk about it doesn't make it worse. It only makes it better.” (15:08)

• Duhigg Agrees: Traumatic experiences become less isolating when someone allows us space to discuss them:

  • “We learn about ourselves by talking…when someone gives us that gift, it's enormous.” (15:21)

6. Power Differentials and Empathy

• Empathy from Authority Figures: Levitt observes that empathy means even more in relationships with a power imbalance, such as teacher-student or doctor-patient.
  • Duhigg gives the example of Dr. Bhafar Adai, a surgeon who improved patient communication dramatically by asking, “What does this diagnosis mean to you?” to elicit patients' real needs (practical, emotional, or social).
  • “He found some people would answer…asking him about treatments. But the vast majority…would talk about illnesses their parents had…They were there not for advice, but to make sense of being sick.” (18:54)

7. Fast Friends, Deep Questions, and Super Communicators

• Nick Epley Example: Both Levitt and Duhigg are struck by Nick Epley’s ability to forge instant connection—by reciprocating vulnerability and asking deeper questions, not through charisma.

  • Duhigg: “If you tell [Nick] something about yourself, he tells you something about himself…It makes it feel so natural to talk about my life.” (22:20–23:25)

• The Hedge Fund Experiment: Epley’s “fast friends” experiment (posing escalating deep questions to strangers) reliably forges emotional bonds—undeniable, even among skeptical type-A executives.

  • “That's the best conversation I've had in years…because they were invited to ask a deep question and answer a deep question...” (25:40–26:06)

8. Levitt's Group Exercise: The Power of Permission and Bragging

• Levitt recounts facilitating a dinner of high achievers, instructing everyone to introduce themselves without any modesty—insisting on full permission to “brag.”

  • The result? 8 strangers end up sharing both triumphs and fears, all eventually crying at a work dinner.
  • “It breaks every social norm about restraint…After we finished, …we ended up…having one of the most wonderful and intimate group conversations…” (27:17–28:44)

• Duhigg links this to “looping for understanding”—a technique of repeating back someone’s statement, then clarifying if you got it right:

  • “By asking them if you got it right, you’re giving them permission to correct you or to say, yes, you understand me.” (28:48)

• Levitt discusses using looping with his wife:

  • “The first time I tried it, I said what I thought she had said, and she's like, no, that's not it at all. …By repeating back…she felt heard.” (30:15–30:54)

9. Lessons from Duhigg’s Other Books

• The Power of Habit:

  • Habits are built of a “cue–routine–reward” loop; understanding and manipulating the loop is the key to changing behaviors—not willpower but engineering your context.
  • Duhigg received over 26,000 emails from readers and personally responds:
    • “As a journalist, you basically just steal other people's ideas and then try and explain them in entertaining ways…I can’t think of something more meaningful…than to help people connect with the people that they love the most.” (34:18–35:47)

• Smarter, Faster, Better (and "Frozen")

  • Levitt is “devastated” to learn that Frozen’s famed story was the result of trial and error, discarded scripts, and blending unrelated elements.
  • Duhigg:
    • “Creativity comes not from a brainstorm… but mixing ideas together in new ways… Behavioral economics is pointed to as the apex of innovation brokerage.” (40:05–41:44)

10. The Levitt/Duhigg Parallel: Borrowing and Remixing

• Both men admit “borrowing” has been at the heart of their own professional breakthroughs; success comes from courageously “asking new questions” and remixing, not clinging to orthodoxy or trying to invent from scratch.

  • Levitt: “All I did was I was myself…I just actually tried to pay attention to what was interesting to me and didn’t worry about whether it’d be interesting to other people…” (43:01–44:03)

• Duhigg observes the meta-cognitive act of successful communication:

  • “If we’re a good communicator…we’re observing ourselves a little bit …This capacity for sort of meta observation … means that our own experiences become a data set that we can learn from.” (44:03–45:08)

Notable Quotes & Memorable Moments

• On Instincts and Conversation:

  • "Part of what I tried to do with the book is to explain how conversations work so that … people can stop thinking about having those conversations. They can let their natural instincts take over." (02:48) — Charles Duhigg

• On the Power of Empathy and Recognition:

  • "[Baristas] melt...when you acknowledge a little bit of emotion." (08:54) — Steve Levitt

• On Looping Technique:

  • “When you say to her, like, here's what I heard you say, and then you screw it all up...What you're really saying is, no, I really want to understand what you're saying.” (30:54) — Charles Duhigg

• On Fast Friends and Connectivity:

  • “That’s the best conversation I’ve had in years…because they were invited to ask a deep question and to answer a deep question…” (25:40) — Charles Duhigg on Nick Epley’s experiment

• On the Reward of Breaking Social Norms:

  • “After we finished, one of the men…said…‘Would it be okay if I also tell you about my deepest regret?’…Every single person at the table cried that night.” (28:19) — Steve Levitt

Key Timestamps

• 01:58 — Levitt on why mastery of conversations matters.
• 03:44 — Duhigg: Book is both “how to” and self-help for himself.
• 06:09–07:37 — Duhigg details 3 types of conversations (practical, emotional, social).
• 08:54 — Levitt describes the effect of attuned communication on strangers.
• 09:58 — Duhigg explains “deep questions.”
• 13:17 — Duhigg on the power of permission in conversations.
• 15:08–15:21 — Both discuss talking about loss and social vulnerability.
• 18:54 — Duhigg shares Dr. Adai's patient strategy: “What does this diagnosis mean to you?”
• 22:20 — Why Nick Epley makes everyone feel like a close friend.
• 25:40 — Epley's hedge fund “fast friends” experiment.
• 27:17 — Levitt on permission-giving through breaking “bragging” taboos at a dinner.
• 30:54 — The value of “looping for understanding” in conflict resolution.
• 32:13 — The simple “habit loop” from Duhigg’s earlier book.
• 34:18 — Duhigg on meaningfulness of reader feedback.
• 38:57 — The surprising and circuitous making of the film Frozen.
• 41:44 — “Innovation brokerage” as the secret to many creative breakthroughs.
• 43:01 — Levitt’s “desperation” led him to break economics rules—and succeed.
• 44:03 — The meta-cognitive power in communication.

Closing

Levitt concludes, almost spellbound by Duhigg’s conversational skill and warmth:

• “I can't stop thinking about how much I love Charles Duhigg, how he feels like a close friend, even though this is the first time we've ever spoken. It's almost like he cast a spell over me. That's how powerful these conversational tools are.” (45:25)

Charles Duhigg caps the episode with excitement for his next project—covering AI for The New Yorker—and an open invitation for listeners' ideas.

In Sum

This episode distills the art and science behind remarkable conversations, showing how curiosity, vulnerability, and conscious permission-giving transform how we connect—whether with family, colleagues, strangers, or even ourselves. Tools like “deep questions” and “looping for understanding” are not just effective—they are transformative, as both research and personal stories vividly illustrate.

Next episode: Harvard psychologist and linguist Steven Pinker returns as Levitt’s guest.