ReThinking with Adam Grant — “The art of the interview with Andrew Ross Sorkin”

Date: October 21, 2025
Host: Adam Grant (Organizational psychologist, author, TED podcaster)
Guest: Andrew Ross Sorkin (NYT DealBook founder, CNBC Squawk Box co-anchor, author of 1929)

Episode Overview

This episode explores the craft of interviewing with world-class journalist Andrew Ross Sorkin. Adam Grant delves into Sorkin’s metaphors and frameworks for interviewing (whether in media, on stage, or in job settings), his strategies for tackling tough topics, and his insights into the psychology of powerful people. The latter part of the episode covers Sorkin’s new book, 1929, unpacking lessons from history’s most infamous stock market crash and reflecting on the enduring human behaviors that drive risk, innovation, and financial bubbles.

Key Discussion Points & Insights

The Interview as Tennis Match (02:35)

• Sorkin’s core metaphor:

  “A great conversation is that you don’t really want to see one person acing the other person... there’s very little to learn from it. You actually want the other person to return the ball... sometimes you’ll place the ball in the corner to see if they can run. And by the way, sometimes they’re going to place the ball in the corner to see if you can run.” (Andrew Ross Sorkin, 03:05)

• It’s not about one-upmanship; the best interviews are dynamic exchanges, not monologues or grillings.

Serving the Audience, Not the Guest (04:03)

• Grant’s early learning:

  “I’m not here for the guest. The guest and I are here for the audience.” (Adam Grant, 04:03)

• Sorkin’s strategy is to convince the guest that serving the audience is ultimately in their own interest.
• When guests are resistant or performative, Sorkin adapts (“through hook or crook, carrot or stick”) to keep things on track.

Preparation & Tackling Tough Topics (06:39)

• Preparation is about “finding the fault lines”:

  “All I’m trying to do when I prepare for an interview is figure out where the fault lines are... I want to know where all the speed bumps are before the interview.” (Andrew Ross Sorkin, 06:39)

• Speed bumps = sensitive areas, tough questions, past mistakes, critiques.
• Tactical approach: Use someone else’s critical quote rather than making it adversarial; it invites the guest to respond thoughtfully, not defensively.

The “Four Walls” Technique (10:29)

• Ask a series of interconnected questions that “build walls,” gradually guiding the guest to a point where they are compelled to answer the difficult issue.
• Grant names this the “four walls technique” from psychology; Sorkin uses it intuitively.

Notes vs. Improvisation: The Perils and Rewards (11:38)

• Both agree: the best and worst interviews can come when you have few prepared notes—it depends on the chemistry and skill of all involved.

  “With great dancing elephants, no notes is ideal because we both end up improvising… some of the worst ones also are when I think I know what’s going to make the person interesting, and I’ve underprepared.” (Adam Grant, 11:46)

The “Dancing Elephant” (01:38; 12:14)

• The host is “an animal trainer”; “you can never blame the elephant.” Success (or failure) always falls on the interviewer.
• Most rewarding interviews are when you get a tough guest—one who “doesn’t want to dance”—to suddenly open up.

Memorable Moment: The Elon Musk Interview (12:41)

• Musk’s famous on-air “F-off” to Bob Iger could have derailed the segment. Sorkin responded by abandoning his plan, diving deep into Musk’s psychological state, which salvaged and deepened the remaining conversation.

  “I could sense he was in this place... maybe we can really do something interesting here, talk about what that place feels like, and then... go to other places afterwards, and happily that happened.” (14:14)

Parallels Between Media & Job Interviews (14:25)

• Sorkin sees strong similarities: both are about “meeting people where they are,” testing how agile they are, and seeing if “they can return the ball.”
• Contrary to popular advice, the goal is not to stump the guest or candidate, but to give them a chance to flourish under fair challenge.

Sorkin’s Practical Tip (16:17)

• Research for ‘speed bumps’: “I will oftentimes write their name and, or their company or institution or affiliation and write the word controversy into Google.” (Andrew Ross Sorkin, 16:17)
• Use AI tools (e.g., ChatGPT) to surface potential critiques or blind spots, even about oneself.

Self-Knowledge, Perfectionism, and the Drive of High Achievers (17:37; 18:48)

• Sorkin confesses to perpetual self-critique, describing himself as a “masochistic narcissist” or perfectionist—always seeking incremental improvements, never fully satisfied.
• Grant reframes this less as narcissism (which defends ego) and more as pro-social, integrity-driven perfectionism.
• Both note that many “shoot-the-moon” achievers are driven by a fundamental insecurity, always trying to prove themselves, even after reaching the apex of their fields:

  “Even the ones who appear to have scaled themselves to the absolute top of the mountain... keep looking up for something else.” (Andrew Ross Sorkin, 20:34)

• Some eventually transcend insecurity, motivated by growth, contribution, and curiosity.

Curiosity and Power (23:09; 24:13)

• The most successful people often start off highly curious—asking questions, exploring new ideas.
• With more success/power, some lose this curiosity, retreating into echo chambers or simply transitioning into “answer mode.”
• Sorkin admires those rare individuals who maintain their curiosity, asking not only grand but even “mundane” questions.

1929: Lessons from the Biggest Crash (28:50)

The Cultural Invention of “Get Rich Quick” (30:33)

• The 1920s birthed the notion of the American Dream as “get rich quick,” celebrity financiers, and excessive risk-taking—parallels abound with today’s culture.
• “Gambling became an American pastime. And I think in many ways, gambling is part of our pastime today.” (Andrew Ross Sorkin, 32:19)

Two Core Lessons from 1929 (33:14)

1. Humility:
   “We’re probably always going to have crashes… the goal probably isn’t to eliminate the bubble completely... the goal is to make sure that the bubble doesn’t get too far out of hand.” (33:14)
2. Speculation as Innovation’s Twin:
   “For innovation to happen, you actually do need speculation. Speculation is the twin of innovation.” (33:14)

The Psychological Impact of Crashes (35:18)

• Personal story: Sorkin’s grandfather, present at the 1929 crash, never invested in stocks afterward—“scarred for life” by that trauma.
• The real danger is not knowing cycles are inevitable:

  “It was like getting hit over the head with a two by four that they didn’t see coming... the more people understand about how the system works… that to me, unto itself, just the information is power to some degree.” (Andrew Ross Sorkin, 36:16)

Lightning Round (39:39)

Worst advice for being interviewed:

“Show up with these three points that they’re supposed to repeat over and over... But the best interviews are the ones where it feels like the person is actually grappling with the question.” (Andrew Ross Sorkin, 39:50)

Who would you most want to interview (alive or dead)?

“Michael Jackson. I can’t even begin to think about how you could unpack that life and those decisions...” (Andrew Ross Sorkin, 40:54)

Hot take to defend:

“Money is not emotional armor.” (Andrew Ross Sorkin, 41:20)
“I know people say like, nothing good happens after midnight. I go with nothing good happens after 8:30.” (41:31)

Notable Quotes & Memorable Moments

• On Interviewing:

  “You are like an animal trainer. It is your job to make the elephant dance. And you can never blame the elephant.” (Andrew Ross Sorkin, 01:38)

• On prepping for tough interviews:

  “Oftentimes a lesson is embedded in the mistake.” (Andrew Ross Sorkin, 07:22)

• On the psychology of high achievers:

  “Most people who’ve had what I describe as shoot the moon success... still feel like they have something to prove...” (Andrew Ross Sorkin, 20:34)

Feedback on Adam Grant’s Interviewing (42:13)

• Sorkin:

  “Pretty great... But if I were to tell you you did terribly and it’s your own podcast, how would that work? Well, I give you an A minus. That means there’s always room for improvement." (Andrew Ross Sorkin, 42:13)

• Highlights value of unpredictability for fostering authentic, unscripted conversation.

Timestamps for Major Segments

• Interview as Tennis Match: 02:35–04:26
• Serving the Audience: 04:03–04:42
• Speed Bumps & Preparation: 06:39–09:03
• The Four Walls Technique: 10:29–11:38
• Improvisation vs. Over-Preparation: 11:38–12:14
• Memorable Musk Interview: 12:41–14:14
• Parallel to Job Interviews: 14:25–16:08
• Using Google & AI for Prep: 16:17–17:58
• Perfectionism & Insecurity: 18:48–20:34
• Curiosity and Power: 23:09–25:27
• Context of ‘1929’ Book: 28:50–31:55
• Lessons from the Crash: 33:14–36:59
• Lightning Round: 39:39–41:59
• Meta-Feedback: 42:13–43:05

Tone & Style

The discussion is candid, self-reflective, sometimes humorous, and always intellectually curious. Both Grant and Sorkin balance humility with deep expertise, using vivid metaphors (“tennis match,” “dancing elephant”) and concrete anecdotes (Elon Musk interview, Sorkin’s family story) to bring abstract ideas to life.

“Life is about hopefully learning about other people.”
—Andrew Ross Sorkin (25:32)

This summary captures the essential content and energy of an episode filled with lessons, behind-the-scenes wisdom, and the human element at the heart of great interviews—on both sides of the mic.