ReThinking: The art of the interview with Andrew Ross Sorkin
Episode
36 min
Read time
2 min
Topics
Career Growth, Productivity, Relationships
AI-Generated Summary
Key Takeaways
- ✓Tennis match framework: Structure interviews as long rallies where both participants hit the ball hard but ensure the other can return it. Place shots strategically to test capabilities without acing opponents repeatedly. This approach serves the audience rather than pleasing the guest, creating more valuable exchanges than one-sided interrogations where learning opportunities disappear.
- ✓Four walls technique: Corner evasive subjects by asking sequential questions that each create boundaries, limiting escape routes. Start with foundational questions that establish positions, then build additional constraints through follow-up queries. This boxing-in method works for investigative contexts where direct answers prove difficult to obtain, forcing engagement with uncomfortable topics through logical progression.
- ✓Speed bump identification: Search the guest's name plus "controversy" in Google before interviews to map potential difficult areas. Share critical quotes from others rather than personal critiques, which removes the interviewer from attack position and acknowledges the guest likely already knows and has considered the criticism, making them more willing to engage substantively.
- ✓Insecurity drives success: Leaders with extraordinary achievements consistently demonstrate underlying insecurity propelling them forward, whether proving themselves to family members, former doubters, or internal standards. Even those appearing supremely confident at career peaks still ask "Was it good?" after conversations. This pattern persists regardless of accomplishment level, fueling continued mountain-climbing rather than satisfaction.
- ✓Curiosity decline with power: Successful people often become less curious as they rise, partly because they shift into answer-giving mode as constant question targets. This represents not curiosity loss but suppressed expression. The most admired leaders maintain curiosity about mundane details despite success, while others create bubbles of yes-people or focus inward, losing the questioning habit that initially drove achievement.
What It Covers
Andrew Ross Sorkin, New York Times DealBook founder and CNBC Squawk Box co-anchor, reveals his interviewing methodology with Adam Grant. Sorkin shares techniques for handling difficult guests, preparing for interviews, and creating productive conversations. He discusses his new book 1929 about the stock market crash and explains psychological patterns among powerful leaders.
Key Questions Answered
- •Tennis match framework: Structure interviews as long rallies where both participants hit the ball hard but ensure the other can return it. Place shots strategically to test capabilities without acing opponents repeatedly. This approach serves the audience rather than pleasing the guest, creating more valuable exchanges than one-sided interrogations where learning opportunities disappear.
- •Four walls technique: Corner evasive subjects by asking sequential questions that each create boundaries, limiting escape routes. Start with foundational questions that establish positions, then build additional constraints through follow-up queries. This boxing-in method works for investigative contexts where direct answers prove difficult to obtain, forcing engagement with uncomfortable topics through logical progression.
- •Speed bump identification: Search the guest's name plus "controversy" in Google before interviews to map potential difficult areas. Share critical quotes from others rather than personal critiques, which removes the interviewer from attack position and acknowledges the guest likely already knows and has considered the criticism, making them more willing to engage substantively.
- •Insecurity drives success: Leaders with extraordinary achievements consistently demonstrate underlying insecurity propelling them forward, whether proving themselves to family members, former doubters, or internal standards. Even those appearing supremely confident at career peaks still ask "Was it good?" after conversations. This pattern persists regardless of accomplishment level, fueling continued mountain-climbing rather than satisfaction.
- •Curiosity decline with power: Successful people often become less curious as they rise, partly because they shift into answer-giving mode as constant question targets. This represents not curiosity loss but suppressed expression. The most admired leaders maintain curiosity about mundane details despite success, while others create bubbles of yes-people or focus inward, losing the questioning habit that initially drove achievement.
Notable Moment
Sorkin reveals his grandfather worked as a messenger boy during the October 1929 crash and never purchased a single stock for the remaining 63 years of his life, convinced the market was too dangerous for common people. This psychological scarring affected an entire generation, demonstrating how financial trauma creates lasting behavioral changes that persist decades beyond the triggering event.
Episode Transcript
This episode is supported by Harvard Business School Executive Education. Their programs create powerful connections for leaders around the world, strengthening both organizations and individuals by deepening existing relationships and fostering new ones. Participants leave with lifelong friends, new potential business partners, and a powerful globe spanning network of fellow change makers. Learn more at hbs.me/learn. That's hbs.me/learn. This message is brought to you by Apple Card. Apple Card members can earn unlimited daily cash back on everyday purchases wherever they shop. This means you could be earning daily cash on just about anything, like a slice of pizza from your local pizza place or a latte from the corner coffee shop. Apply for Apple Card in the Wallet app to see your credit limit offer in minutes. Subject to credit approval, Apple Card issued by Goldman Sachs Bank USA, Salt Lake City branch. Terms and more at applecard.com. This episode is sponsored by Gab. We know that social media plays a role in today's youth mental health crisis. Teens now spend an average of nine hours a day on screens outside of school. That's essentially a full time job. But there's good news. There's a company called Gabb that's tackling the problem by doing something different. They're introducing tech in steps. Gabb's Kidsafe phones and watches are designed specifically for growing kids, starting with GPS enabled watches for younger children and evolving into phones with more features for tweens and teens, all with strong parental controls. Bottom line, you don't have to hand your kid a device made for an adult. Give them Gab so they can stay connected safely. Visit gab.com/worklife and use code work life for a special offer. That's gabb.com/worklife. I always say you can never actually blame the guest. 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. Hey, everyone. It's Adam Grant. Welcome back to Rethinking, my podcast with Ted on the science of what makes us tick. I'm an organizational psychologist, and I'm taking you inside the minds of fascinating people to explore new thoughts and new ways of thinking. My guest today is Andrew Ross Sorkin, my favorite business journalist. He writes for the New York Times deal book, which he founded, and co anchors Squawk Box on CNBC. Over the years, Andrew and I have had some fascinating conversations about the psychology that drives some of the most powerful people of our time. And he's equally interested in the financial decision makers who lived almost a century ago during the stock market crash of nineteen twenty nine. So interested, in fact, that he wrote a riveting new book about it called 1929. Before we dig into that, I wanted to talk to him about interviewing because he's a world class interviewer. You introduced me last year to what has become my favorite metaphor for an interview that becomes a great …
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by Andrew Ross Sorkin
“He discusses his new book 1929 about the stock market crash and explains psychological patterns among powerful leaders.”
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