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.

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 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.

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.

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.

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.

The most driven entrepreneurs are often fueled by foundational traumas. Understanding a founder's past struggles—losing family wealth or social slights—provides deep insight into their intensity, work ethic, and resilience. It's a powerful, empathetic tool for diligence beyond the balance sheet.

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.