ReThinking: The art of the interview with Andrew Ross Sorkin

What if a great interview felt like a long tennis rally?

Here's what stood out to me: Andrew Ross Sorkin, a forensic observer of markets and people, treats conversation as choreography. He wants rallies—long, unpredictable exchanges where both players keep returning the ball. That image stuck with me because it flips the usual interview goal on its head. The aim isn't to score points or get soundbites. It's to sustain momentum until something surprising reveals itself.

The art of making the elephant dance

There is a blunt admission at the center of Sorkin's approach: the host is responsible for the performance. That felt refreshingly democratic. He compares guests to animals trainers face—sometimes the elephant refuses to move—and he takes the blame when a conversation stalls. What I liked most was his practical humility. He prepares for "speed bumps": the tricky subjects, the mistakes, the criticisms that will likely trip a guest up. Then he uses tactics that feel more humane than ambush—reading a critical quote aloud, signaling that a question is difficult, or building a sequence of questions that gently corners an evasive answer.

Techniques that actually work

Sorkin borrows from sport and psychology with the same ease. He names the "four walls" technique without preaching: stack questions so a guest's own answers make it harder to avoid the truth. He also values curiosity over performance. The best leaders he profiles are not those who always have answers; they're the ones who ask good questions. That was a surprising reminder—power often amplifies existing traits, but curiosity can protect leaders from the bubble of yes-men.

Personally, I found his blunt take on preparation oddly comforting. Instead of rehearsed talking points—"three things to repeat"—Sorkin advises being present. Answer the question first. Pivot later if you must. That felt like medicine for modern media's soundbite addiction.

From interviewing to hiring

One neat crossover: interviewing for media and interviewing for jobs share the same essential test—can the person return the ball? If your goal is to simulate real work, then an interrogative grilling that seeks to embarrass is counterproductive. Instead, create a court where candidates can demonstrate skills under realistic conditions. That was an immediately useful idea for managers and podcasters alike.

History as a mirror: 1929 and the psychology of risk

Sorkin's new book, 1929, reads like a character study of ambition, temptation, and national mood. He argues that the 1920s birthed a modern culture of celebrity around wealth and a particular appetite for speculation. The takeaway surprised me: the memorable public faces of business—bankers and tycoons on magazine covers—weren't common before the 1920s. Suddenly finance became glamorous and stock trading turned into a pastime you could do almost anywhere.

I kept thinking about an image Sorkin shared: you could buy stock with a dollar while the bank lent the rest. That ease of leverage made the upside feel almost frictionless. Gambling greased into daily life. And like any wound left untreated, the crash left psychological scars. Sorkin remembers his grandfather, a messenger during the crash, who never bought stock again. The human fallout extended far beyond balance sheets.

Two stubborn lessons

Sorkin lands on a difficult pair of conclusions. First: humility. Bubbles will likely recur, and we need guardrails to limit damage without extinguishing growth. Second: speculation fuels innovation. Without people willing to back wild ideas, progress stalls. These claims felt contradictory until he reconciled them: the goal is not to stop speculation, but to manage its scale and consequences.

I found that argument emotionally resonant. It's tempting to demand absolute safety after a crash, but we might also kill the risk-taking that births transformative companies. The question becomes not whether to allow speculation, but how to design institutions and norms that absorb contagion while preserving imaginative bets.

Small rituals, big effects

Some of Sorkin's smallest habits reveal the mind of a journalist: typing a name plus "controversy" into Google before an interview, or asking guests to respond to a quote rather than confronting them directly. Those tactics remove ownership of nastier questions and give interviewees room to explain. They are deceptively effective because they respect the person while serving the audience.

Honestly, I didn't expect to feel both reassured and unsettled. Reassured because conversation can be crafted; unsettled because the forces that made the 1920s risky—easy credit, celebrity culture, a taste for lottery-like gains—recur in our own finance and tech moment. What if the dynamics haven't changed as much as we like to believe? That question lingered with me long after the credits.

Final thought: Good conversations are constructed to coax truth, not to humiliate; history reminds us that human appetite for risk is both a motor of progress and a persistent hazard.