Fixable: The Art of the Interview with Andrew Ross Sorkin

From: ReThinking with Adam Grant | Published: December 22, 2025

Episode Overview

This episode features a conversation between organizational psychologist and host Adam Grant and renowned business journalist Andrew Ross Sorkin. They explore "the art of the interview," delving into the psychology and techniques behind great conversations both in media and in job interviews. The discussion extends from the nuances of hosting high-stakes interviews to Sorkin’s new book, 1929, which examines the personal forces behind the world’s most infamous financial crash. The episode is a masterclass in interviewing, curiosity, and understanding what drives high achievers, offering advice that is as practical for the boardroom as it is for broadcast.

Key Discussion Points & Insights

1. The Art and Psychology of Interviewing

• Interview as a Tennis Match

  • Sorkin encourages seeing interviews as an engaging tennis match, not a contest of aces:

    "To me, a great conversation is that you don't really want to see one person acing the other person over and over again...it just makes for a much more interesting dialogue." (Andrew Ross Sorkin, 03:58)

  • Both parties should return the ball; well-placed questions test capability but foster connection.

• Responsibility of the Host

  • The host is fully accountable for orchestrating a good interview:

    "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, 02:31)

  • Great hosts shift guests’ focus from self-promotion to audience value.

• Navigating Uncooperative Guests

  • When guests aren’t engaging, Sorkin adjusts strategies depending on the format (e.g., taking a commercial break on TV, creatively steering conversation on stage).

    "It is on you to figure out how... you are going to make it work." (Sorkin, 06:09)

• Preparation Techniques

  • Sorkin prepares by identifying "fault lines" and "speed bumps":

    “I desperately try to put myself in their shoes. I wanna know where all the speed bumps are before the interview.” (Sorkin, 07:31)

  • He may read critical quotes to guests, using others’ critiques to disarm defensiveness and encourage honest discussion.

• Handling Difficult Topics

  • Prefaces hard questions by acknowledging their difficulty, inviting the guest to join in addressing them:

    “I say, ‘this is a difficult question,’ or ‘here's a complicated question,’ and it's just another way of trying to meet people where they are and acknowledge to them that I understand that this is not easy.” (Sorkin, 09:08)

• Types of Interviews and "Four Walls" Technique

  • Interviews range from friendly explorations to investigative interrogations; Sorkin sometimes uses the "four walls" technique—sequencing questions to create a logical pathway the guest can’t evade.

    “Sometimes you have to corner people if you're trying to get to a particular kind of truth.” (Sorkin, 11:47)

• Improvisation vs. Over-preparation

  • Both agree that few notes can foster unexpected, lively conversations with a skilled subject but can backfire with less forthcoming guests.

    “Some of the worst ones also are when I think I know what's gonna make the person interesting. And I've underprepared as a result, and it just doesn't land.” (Grant, 12:58)

2. Stories from the Field: Interviewing Elon Musk

• Sorkin recounts a high-tension moment interviewing Elon Musk, who made headlines telling Bob Iger to "go f*ck yourself" regarding advertising on X (Twitter):
  • Sorkin adapted by shifting focus from business topics to Musk's personal motivations, successfully redirecting the dialogue:

    “I could sense he was in this place...so we started really talking about where all of this comes from in him...and then once we could go deep there, then we could go to all these other places afterwards.” (Sorkin, 14:14)

3. Parallels Between Media and Job Interviews

• Sorkin draws a direct parallel between media interviewing and job interviewing—both aim to create a give-and-take akin to his tennis metaphor:

  • Good interviews allow the candidate to "return the ball," showcasing authentic strengths rather than tripping them up with gotcha questions.

    "What I'm trying to do in my own way is to meet them where they are....In a job interview, I'm hoping they hit the ball back." (Sorkin, 15:18)

• Adam Grant reflects that the most effective job interviews replicate the real working environment’s give-and-take, rather than pressure-cooker scenarios.

4. Practical Interviewing Tips

• Research 'Controversy': Sorkin Googles "[Name] + controversy" before high-profile interviews to anticipate tough questions.

  "It's just an easy, silly thing...just to find the speed bumps." (Sorkin, 17:10)

• Self-analysis: Sorkin once asked ChatGPT to provide critical feedback about himself, finding value in self-awareness (with a nod to the "Forer/Barnum effect" of generalized feedback).

  “I am narcissistic enough to know all of the problems. I just don't know how to fix them all.” (Sorkin, 18:45)

• Perfectionism & Improvement: Sorkin and Grant discuss their drive for continual self-improvement—a double-edged sword of perfectionism.

  "It's a constant sense of trying to make everything better, of trying to fix it..." (Sorkin, 19:49)

5. Psychology of Powerful People

• Sorkin observes that many high achievers are propelled by insecurities, regardless of their outward success:

  “Despite all of the success, still feel like they have something to prove...even the ones who appear to have scaled themselves to the absolute top..." (Sorkin, 21:27)

• Curiosity is often high in great leaders, but may wane as they accrue power and "answers" become expected of them rather than questions.

  “Some of the most successful people in the world are the most curious...one of the things that does happen with great success is that they...become less curious.” (Sorkin, 23:51)

Notable Quotes and Memorable Moments

| Timestamp | Quote | Speaker | |-----------|-------|---------| | 02:31 | "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 | | 03:58 | "A great conversation is...a long, long match...you actually want the other person to return the ball." | Sorkin | | 05:07 | "...it's incumbent upon me to convince the guest that it's actually in their interest to serve the audience." | Sorkin | | 07:31 | "I desperately try to put myself in their shoes. I wanna know where all the speed bumps are before the interview." | Sorkin | | 09:08 | "...this is a difficult question, or here's a complicated question, and it's just another way of trying to meet people where they are..." | Sorkin | | 11:47 | "Sometimes you have to corner people if you're trying to get to a particular kind of truth." | Sorkin | | 12:58 | "Some of the worst ones also are when I think I know what's gonna make the person interesting. And I've underprepared as a Result." | Adam Grant | | 14:14 | (Musk interview shift) "I could sense he was in this place...so we started really talking about where all of this comes from in him..." | Sorkin | | 15:18 | "...what I'm trying to do in a job interview...is to meet them where they are...hoping they hit the ball back." | Sorkin | | 18:45 | "I am narcissistic enough to know all of the problems. I just don't know how to fix them all." | Sorkin | | 19:49 | "It's a constant sense of trying to make everything better, of trying to fix it..." | Sorkin | | 21:27 | "...most people who've had what I describe as shoot the moon success...still feel like they have something to prove..." | Sorkin |

Deep Dive: Andrew Ross Sorkin’s "1929"

(29:39 – 37:46)

• Book Premise:
  Sorkin discusses his new book, 1929, exploring not just the crash but the characters, motivations, and psychology behind it.

  "...trying to go back in history and try to understand...what drove them both before the crash to make the mistakes that they made..." (Sorkin, 29:51–31:10)

• Revelation:
  The American Dream's current incarnation—wealth as celebrity, get-rich-quick—arose from the culture and accessible credit of the 1920s.

  “The whole sort of like, get rich quick idea was actually like a very 1920s idea..." (Sorkin, 31:21)

• Lessons from 1929:

  1. Humility in the face of inevitable bubbles and crashes:

     “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." (Sorkin, 34:02)

  2. The necessity of some speculation for innovation:

     “Speculation is the twin of innovation...Elon Musk could not have had success unless somebody was willing to speculate on him." (Sorkin, 34:02)

  3. The lasting psychological scars that market crashes leave on individuals, illustrated by his grandfather’s lifelong mistrust of stocks.

     "My grandfather, who lived till 92, never bought a share of stock...after that....he really believed that the stock market was this very dangerous place..." (Sorkin, 36:05)

Lightning Round & Advice Highlights

(40:23 – 43:10)

• Worst Interview Advice:

  "...to show up with these three points that they're supposed to repeat over and over ...the best interviews...are the ones where it feels like the person is actually grappling with the question." (Sorkin, 40:34)

• Dream Interviewee:
  Michael Jackson—for understanding the psyche behind such a unique and turbulent life.
  (41:30)

• Hot Take:

  "Money is not emotional armor." (Sorkin, 42:05)

  • Most people believe money protects against emotional hardship, but Sorkin argues otherwise.

• A Life Maxim:

  "Nothing good happens after 8:30" (rather than the cliché "after midnight"). (Sorkin, 42:16)

• On Adam Grant’s Hosting Skills:
  Sorkin awards Grant an A- for creating an open and serendipitous space, noting the tradeoff between surprise and prepared (possibly canned) responses.

  "But if I were to tell you you did terribly and it's your own podcast, how would that work? Well, I'd give you an A minus. That means there's always room for improvement." (Sorkin, 43:09)

Key Timestamps for Major Themes

• Interviewing as Tennis Match/Host Responsibility: 02:31–05:35
• Difficult Guests/Ethics of Interviewing: 05:54–07:19
• Preparation & Handling Criticism: 07:31–09:56 & 10:42–12:31
• Improvisation & Elephant Metaphor: 12:31–13:28
• Musk Interview Example: 13:33–15:13
• Job Interviews as Conversations: 15:14–17:10
• Preparation Tricks (Google/AI): 17:10–19:11
• Insecurity & Psychology of Leaders: 21:13–26:25
• Sorkin’s Book ‘1929’: 29:39–37:46
• Lightning Advice & Rapid Fire: 40:23–43:10

Final Takeaways

• The best interviews—media or job—are interactive, authentic conversations that create space for both parties to surprise one another.
• Preparation means understanding the subject from multiple angles and anticipating challenges, but also remaining flexible and in-the-moment.
• High achievers, despite outward confidence, often operate from a place of healthy (or sometimes unhealthy) insecurity—one that can drive, but also scar.
• Curiosity, humility, and self-awareness are traits found in the best leaders, journalists, and interviewers.
• History teaches that speculation, risk, and bubbles are part of innovation, but they require humility and safeguards.

This episode is an essential listen for anyone wanting to level up their interviewing technique, gain insight into the psychology of successful people, or understand the timeless dynamics behind financial booms and busts.