Episode 665: Jeffrey Sonnenfeld
July 3rd, 2026
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Understanding Trump’s Leadership Tactics and How to Counter Them
Jeffrey Sonnenfeld is a professor of management and senior associate dean for leadership studies at the Yale School of Management. He is also the author, co-author, and editor of a number of books. His works include The Hero's Farewell: What Happens When CEOs Retire, Firing Back: How Great Leaders Rebound After Career Disasters, and, most recently, Trump's Ten Commandments: Strategic Lessons from the Trump Leadership Toolbox with Steven Tian.
Greg and Jeff discuss why Jeff thinks leadership scholars and journalists misread Donald Trump. He argues the goal should be not to normalize or judge Trump but to understand Trump’s predictable, strategic patterns—often mistaken as impulsive—so they can be countered, and he criticizes the labeling Trump as “stupid” or “crazy” for helping create widespread complacency.
Jeff recounts a contentious 30-year relationship with Donald Trump that began with his Wall Street Journal critiques of “The Apprentice,” and then continued through Trump’s attempts to win him over (including with a position at Trump University), and Trump’s use of tactics like divide-and-conquer, distraction, the “sleeper effect,” and “wall of sound.” The discussion contrasts personal power versus institutional success,and stresses collective action as an effective counter.
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Episode Quotes:
The danger of underestimating your opponent
04:11: My take on this, in short, is the most dangerous element of American society, after perhaps Donald Trump and some of his acolytes, are many of his critics because his critics give us a false sense of confidence by, for over 10 years now, calling him stupid and calling him crazy. More recently, he's had a break with reality, a sudden cognitive decline with age, and chortling to themselves in their articles to one another like love letters in Atlantic Magazine or giggling on show after show on MS Now. It's about as dangerous, almost, as what Trump and his immediate followers are doing themselves because it's giving the American public, their viewers and readers, a false sense of security that this is a guy who is veering off the edge of the cliff and about to implode, that we don't need to worry.
Don’t mistake emotion for impulse
05:14: What Trump does sometimes comes with a lot of emotion-laden packaging, but these aren't impulsive, accidental decisions he's making. These are strategic, decisive, definitive moves that he's making, and that he has a whole arsenal of them.
How to counter divide and conquer
50:18: How do you prepare for false information? Be ready to counter it very quickly and to make sure you're not divided by one another and all these other kinds of things. How do you counter false information? How do you avoid divide and conquer? You know, those are the lessons from the book rather than to follow these tactics.