True story: In the late ‘90s, when I was editing Derivatives Week, I tried to hire a kid straight out of college to join my team. He was obviously bright & curious, had Wall Street connections and had already had several stories published as a mere intern at the New York Times.
Alas, this promising reporter went for the glamour of the glossy—rather than the glory of breaking news on the swap market or the latest structured note offering from UBS—and instead accepted an offer from Businessweek.
Since that time, it’s been a marvel watching Andrew Ross Sorkin’s career take off. He became a star M&A reporter back at the Times and founded the Gray Lady’s DealBook section. He penned Too Big to Fail: The Inside Story of How Wall Street and Washington Fought to Save the Financial System—and Themselves, the widely popular book that won the 2010 Loeb Award for best business book of the year and was even turned into a movie. Then, in 2011, while remaining DealBook editor, he became a co-anchor on CNBC’s Squawk Box where he has interviewed CEOs, investment legends and even presidents. He is the author of the new book 1929, which is likely to be on Wall Street’s reading lists this year
If nothing else, let it be noted that I have a keen eye for spotting future finfluencers!
Sorkin recently sat down on Adam Grant’s Re:Thinking podcast for an interview about the art of interviewing (how very meta). The entire conversation is worth a listen, but here are his main pointers for interviewees and interviewers from one of the best in the business:
For Being Interviewed
Engage genuinely with each question instead of just repeating pre-prepared talking points. Audiences respond best when it feels like the interviewee is thinking and grappling with the subject in real time. We wholeheartedly agree with this advice. As a PR professional, I always coach clients to be prepared to include your key messages, but not be overly scripted. I have seen interviews go pear-shaped when a client steamrolled the interviewer with their talking points instead of having a a give and take conversation.
Master the artful pivot: While it’s important to communicate your core messages, credibility increases when you listen and respond directly to the interviewer’s specific questions before connecting back to your key themes.
Accept that serendipity and improvisation often lead to the best interviews. Over-preparation can limit spontaneity, so balance those thematic talking points you carefully internalized with the flexibility to adapt based on the conversation’s direction.
For Conducting Interviews[JL1] [GJ2]
Treat interviews as a collaborative “tennis match.” The goal is a dynamic, back-and-forth dialogue—aim for exchanges where both interviewer and guest actively build on each other’s ideas rather than dominating or “acing” the conversation.
Prioritize serving the audience over pleasing the guest. The host’s responsibility is to create an environment where valuable insights are shared for the audience’s benefit. He doesn’t want to appear too cool for school or overly chummy with the guest.
Prepare[JL3] by identifying “fault lines” and likely speed bumps—Sorkin says he simply Googles the guest name and “controversy.” Research the difficult areas, controversies, or critiques relevant to the interviewee, and learn ways to approach touchy topics. Framing tough questions as someone else’s critique is a diplomatic way to engage the guest and avoid them shutting down because they feel directly and personally attacked by the person doing the interviewer. I would add that it’s a good idea to be specific here—say, by reading a quote by a third person or showing a video clip.[JL4] [GJ5] The overly generic “some people are saying you …” comes across as contrived or even disingenuous.
The bottom line from Sorkin—and it’s good advice, whether you’re prepping for a guest appearance on CNBC or launching your own podcast—is to approach interviews as opportunities for learning and authentic exchange. They’re not a performance or a cross examination of a hostile witness.
The best interviews are candid, audience-focused, and open to unexpected turns.
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