Sorkin discovered that the direct reply function of his Dealbook newsletter created an invaluable feedback loop. High-profile readers, including dealmakers he was covering, would respond directly with corrections, insider documents, and story leads, turning the audience into a primary source.
Andrew Ross Sorkin emphasizes that for the DealBook Summit, the audience is as important as the stage talent. By filling the room with peers and other influential leaders, speakers feel compelled to engage more deeply, knowing they are being judged by people whose opinions matter to them.
Andrew Ross Sorkin's best sources are often "jilted" individuals—bankers who lost a deal, executives passed over for promotion, or spurned partners. These sources have nothing to lose and are motivated to talk, providing reporters with a powerful, albeit biased, starting point for a story.
Sorkin prepares for interviews by mapping a "flight path"—knowing the start, end, and key topics. However, he expects "weather" (unexpected answers) to force diversions. This mental model provides structure while allowing the flexibility to listen and react, which is the key to a great interview.
Andrew Ross Sorkin argues against the conventional wisdom of professional detachment. He observes that the most successful people take everything personally because they care immensely about the quality of their work. This personal stake, while sometimes painful, is what drives them to achieve greatness.
Andrew Ross Sorkin believes the most crucial moment of an interview is the brief, informal interaction just before it officially begins. This is the window to calm a guest's nerves, build rapport, and set a tone that encourages candor, which is more important than the first question asked.
Instead of asking for confirmation on a rumor, Sorkin's method is to build the story almost completely with details from various sources. By the time he asks the company for comment, he presents so many facts that they are incentivized to cooperate and shape the narrative, rather than just deny it.
Andrew Ross Sorkin launched the Dealbook email newsletter in 2001 not as a grand innovation, but as a defensive tool to bypass the physical paper and reach Wall Street professionals who preferred the Wall Street Journal. It was an internal disruption designed to capture a key audience the main product was missing.
To broach a sensitive topic, Andrew Ross Sorkin reads a critical quote from another source. This technique shifts the focus from a personal attack ("I think you...") to a public concern ("Others are saying..."). It forces the interviewee to grapple with an issue they have likely already considered, leading to a more thoughtful response.