ReThinking: The art of the interview with Andrew Ross Sorkin
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In this fascinating episode of Rethinking, organizational psychologist Adam Grant sits down with master interviewer Andrew Ross Sorkin, the business journalist behind The New York Times DealBook and co-anchor of CNBC's Squawk Box. The conversation dives deep into the psychology of elite interviewing, exploring Sorkin's tennis match metaphor for great conversations and his philosophy that successful interviews require making the "elephant dance." (02:00) The discussion then shifts to Sorkin's new book "1929," examining the behavioral psychology behind history's most infamous financial crash and the powerful figures who both caused and failed to recover from it.
- Main Theme: The art of elite interviewing, the psychology of powerful people, and lessons from the 1929 financial crash that remain relevant today
Speakers
Adam Grant
Adam Grant is an organizational psychologist at Wharton and the host of TED's Rethinking podcast. He's a bestselling author known for books like "Think Again" and "Give and Take," and is recognized as one of the world's top management thinkers for his research on motivation, generosity, and challenging conventional wisdom.
Andrew Ross Sorkin
Andrew Ross Sorkin is a leading business journalist who founded and writes The New York Times DealBook column and co-anchors CNBC's Squawk Box. He's the author of the bestselling book "Too Big to Fail" about the 2008 financial crisis and his latest work "1929" about the stock market crash. Sorkin has established himself as one of the premier interviewers of CEOs, politicians, and other powerful figures in business and finance.
Key Takeaways
Master the Tennis Match Philosophy of Interviewing
Sorkin reveals that great interviews are like tennis matches where both participants want long, engaging rallies rather than quick aces. (03:17) The goal isn't to make your guest look foolish or to simply please them, but to create conditions where both interviewer and interviewee serve the audience by hitting challenging shots that the other person can still return. This approach transforms interviews from interrogations or softball conversations into dynamic exchanges that reveal authentic insights. Whether you're conducting job interviews, leading team meetings, or having difficult conversations, applying this tennis match mentality means preparing thoughtful questions that challenge people while still giving them the opportunity to showcase their best thinking.
Identify Speed Bumps Before They Derail the Conversation
Effective preparation involves mapping out potential "speed bumps" - sensitive topics, past mistakes, or controversial decisions that could cause a guest to shut down. (07:35) Sorkin's approach isn't to avoid these topics but to understand them deeply so he can navigate around them or address them constructively. He suggests using Google searches combining someone's name with "controversy" to uncover these areas. For any important conversation, whether it's a performance review, client meeting, or difficult personal discussion, research potential friction points beforehand so you can address them thoughtfully rather than stumble into them blindly.
Use the "Four Walls" Technique to Corner Difficult Truths
When you need to get to an important truth, Sorkin employs what Grant calls the "four walls technique" - asking a series of questions that create logical boundaries, making it increasingly difficult for someone to avoid giving a direct answer. (10:53) Each question builds on the previous response, creating constraints that eventually box in the respondent. This isn't about being manipulative but about creating a logical progression that leads naturally to the truth. In workplace situations, this might mean asking about goals, then resources, then timelines, and finally accountability, making it harder for someone to avoid taking ownership of results.
Present Criticism Through Third-Party Perspectives
Rather than directly confronting someone with your own critical observations, Sorkin recommends reading them a critical quote from someone else and asking them to respond. (08:26) This technique removes you from the position of attacker and positions you as a neutral moderator while still addressing difficult topics. The person being questioned has likely seen the criticism before and has had time to formulate a thoughtful response. This approach works in professional settings when addressing performance issues, strategic disagreements, or team conflicts - instead of saying "I think you handled this poorly," try "Some people have said X about this situation. How do you respond to that perspective?"
Recognize That Power Amplifies Underlying Insecurity
Despite appearances, most highly successful people continue to feel they have something to prove, driven by underlying insecurities that propel them forward. (20:51) Even those who reach the pinnacle of success don't simply "ski down the mountain" - they keep looking for the next peak to climb. Sorkin observes that this insecurity, when channeled healthily, becomes a driving force for continued achievement and contribution. Understanding this dynamic can help you better relate to high achievers, provide more effective feedback to ambitious team members, and recognize that confidence and competence don't eliminate the fundamental human need for validation and growth.
Statistics & Facts
- You could buy stock in the 1920s with just $1 down while the bank provided the other $10, creating 10-to-1 leverage that made gambling on stocks accessible to ordinary people. (32:26)
- There were stock brokerages on street corners in New York during the 1920s "like there's Starbucks" today, and you could trade stocks in hotels, making speculation ubiquitous. (32:45)
- Based on LinkedIn data, 72% of small businesses using LinkedIn say it has helped them find high-quality candidates for their organizations. (38:41)