WorkLife with Adam Grant
Episode: ReThinking: The art of the interview with Andrew Ross Sorkin
Release Date: October 21, 2025
Host: Adam Grant
Guest: Andrew Ross Sorkin
Overview
In this episode of WorkLife, Adam Grant sits down with acclaimed business journalist Andrew Ross Sorkin to unpack the art of interviewing—what makes for a compelling on-stage conversation, how to handle challenging guests, and the psychological lessons embedded in both public interviews and private job interviews. Sorkin, author of the new book 1929 about the infamous stock market crash, reflects on the motivations and mindsets of the powerful, and shares insights into how historical risk-taking and speculation shape our modern understanding of the American Dream.
Key Discussion Points & Insights
1. Interviewing as a Collaborative “Tennis Match”
- Metaphor for Interviews: Sorkin describes a great interview as a long, engaging tennis rally, rather than one-sided domination.
- “A great conversation is that you don't really want to see one person acing the other person over and over again... It's important that the other person can return the ball.” – Andrew Ross Sorkin [03:26]
- Serving the Audience First: Both agree that the objective of an interview isn’t to please the guest or the host, but to create value for the audience.
- “I'm not here for the guest. The guest and I are here for the audience.” – Adam Grant [04:23]
2. Handling Difficult Guests & Unexpected Moments
- Responsibility of the Host: Sorkin believes the onus is always on the interviewer to guide the conversation, even with tough guests.
- “You are like an animal trainer. It is your job to make the elephant dance and you can never blame the elephant. And that is the responsibility of the host.” – Andrew Ross Sorkin [01:58]
- Strategy with Reluctant Guests: When guests aren’t engaging, Sorkin adapts—switching topics, changing approaches, or using breaks to reset.
- “If we're on television, we go to commercial... If it's on a stage, more complicated... through hook or crook... you are going to make it work.” – Andrew Ross Sorkin [05:24]
3. Preparing for Tough Questions (“Speed Bumps”)
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Identifying Fault Lines: Sorkin emphasizes mapping out contentious or sensitive topics before the interview.
- “All I'm trying to do when I prepare for an interview is figure out where the fault lines are. That’s literally what I'm always trying to do.” – Andrew Ross Sorkin [06:59]
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Techniques for Difficult Topics:
- Presenting critiques using third-party quotes to disarm defensiveness.
- Warning guests before sensitive questions (“this is a tough question”).
- Drawing parallels to investigative vs. collaborative interview styles.
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Four Walls Technique:
- Adam describes a psychological method used to “corner” the guest into answering by sequentially narrowing options.
- “You’re getting them to answer a first question... and eventually they're in a box...” – Adam Grant [10:57]
4. Improvisation vs. Structure in Interviews
- Risk and Reward of Spontaneity: Both discuss how interviews with less preparation can be the best or worst, depending on guest engagement.
- “Your best and worst are the few, both extremes. And it really depends on... a good dancing elephant...” – Adam Grant [11:58]
5. Job Interviews vs. Media Interviews
- Similar Principles: Sorkin sees strong overlap in creating conditions for candidates or guests to demonstrate their best, not setting traps.
- “I often find that a lot of the same things I try to do in an interview on TV... are almost identical to the things I’m trying to do in a job interview.” – Andrew Ross Sorkin [14:46]
- Testing with Challenge: “You're both trying to give the person a chance to show their strengths. But you're also, you're not just hitting them lobster, you're hitting a cross court shot...” – Adam Grant [15:34]
6. Psyche of High Performers & Success
- Enduring Insecurity: Sorkin shares that many ultra-successful figures are still driven by a sense of having “something to prove.”
- “Despite all of the success, [they] still feel like they have something to prove, that there's some underlying almost insecurity...” – Andrew Ross Sorkin [20:54]
- Curiosity at the Top: The most successful remain curious, though some lose this trait as attention and power increase.
- “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.” – Andrew Ross Sorkin [23:30]
7. The Psychology and History of Financial Risk (1929)
- Cultural Roots of Today's Speculation: Sorkin situates the “get rich quick” mentality and business celebrity in the 1920s.
- “The whole sort of, get rich quick idea was actually like a very 1920s idea.” – Andrew Ross Sorkin [30:20]
- Lessons from the Crash:
- Recognize the inevitability of bubbles; the goal is to regulate, not eliminate, risk.
- “For innovation to happen, you actually do need speculation. Speculation is the twin of innovation.” – Andrew Ross Sorkin [33:01]
- Behavioral Scarring: Sorkin shares his grandfather’s lifelong aversion to stocks after witnessing the crash firsthand.
- “My grandfather... never bought a share of stock... his entire life after that. He really believed that the stock market was this very dangerous place.” – Andrew Ross Sorkin [35:04]
8. Lightning Round
- Worst Interview Advice: “Show up with these three points that they're supposed to repeat over and over and over again... The best interviews... are the ones where it feels like the person is actually grappling with the question.” – Andrew Ross Sorkin [40:17]
- Dream Interview (Dead or Alive): Michael Jackson, due to his enigmatic life and complex decisions. [41:13]
- Hot Take: “Money is not emotional armor.” – Andrew Ross Sorkin [41:47]
- Morning Lifestyles: Sorkin humorously claims, “I go with, nothing good happens after 8:30.” [41:58]
9. Self-Reflection and the Drive to Improve
- Perfectionism vs. Narcissism:
- Sorkin and Grant debate the mix of self-critique and motivation that drives improvement in their work.
- “It's a constant sense of trying to make everything better...” – Andrew Ross Sorkin [19:08]
Notable Quotes & Memorable Moments
- “You can never blame the guest... It is your job to make the elephant dance and you can never blame the elephant.” – Andrew Ross Sorkin [01:58]
- “I'm rooting for a long, long match. That's what I want. To me, a great conversation is that.” – Andrew Ross Sorkin [03:26]
- “It takes it out of being your critique, it’s somebody else’s critique.” – Andrew Ross Sorkin on handling criticism in interviews [08:00]
- “Speculation is the twin of innovation.” – Andrew Ross Sorkin [33:01]
- “Money is not emotional armor.” – Andrew Ross Sorkin [41:47]
- “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.” – Andrew Ross Sorkin to Adam Grant [42:42]
Timestamps for Important Segments
- 01:58 – Sorkin: The “elephant dance” metaphor for interviewing
- 03:26 – Tennis match as the ideal interview dynamic
- 06:59 – Preparing by finding “fault lines” and “speed bumps”
- 10:57 – The “four walls” technique for getting honest answers
- 14:46 – Overlap between media interviews and job interviews
- 20:54 – The psychology of powerful, successful people
- 30:20 – How the “American Dream” and financial risk culture began in the 1920s
- 33:01 – Lessons from 1929: bubbles, speculation, and innovation
- 40:17 – Worst advice for being interviewed
- 41:47 – Hot take: “Money is not emotional armor.”
- 42:42 – Sorkin’s feedback on Adam Grant as a host
Final Thoughts
This episode reveals the intentional craft behind great interviews, from mapping the conversational terrain to handling live surprises. Sorkin’s perspectives illuminate the parallels between public interviews, job assessments, and life itself: curiosity, adaptability, and a focus on genuine engagement are universal differentiators. The discussion on financial history reframes current economic attitudes as deeply ingrained social phenomena, and both host and guest exemplify a restless drive for improvement even at the top of their fields.