unSILOed with Greg LaBlanc

665. Understanding Trump’s Leadership Tactics and How to Counter Them with Jeffrey Sonnenfeld

unSILOed with Greg LaBlanc

Show Notes

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.

*unSILOed Podcast is produced by University FM.*

More from unSILOed with Greg LaBlanc

Oct 22, 2026

The term “Luddite” is often used today in a pejorative way for people standing in the way of progress and averse to technology. But for the Luddites of the 19th century, pushing back against technological advancements was a matter of life and death.

Oct 20, 2026

Meghan O’Gieblyn is a writer who writes on the interface of technology and humans. Her latest books are titled Will and Attention: A Memoir and the book God, Human, Animal, Machine: Technology, Metaphor, and the Search for Meaning. Greg and Meghan discuss Max Weber’s disenchantment thesis, whether technology and AI re-enchant the world, and how opaque algorithmic systems invite faith-like deference while also prompting anthropomorphism and mechanistic views of the mind. Meghan explores how metaphors in religion and AI become literalized, complicating concepts like intention and consciousness. Turning to will and willpower, she connects her Calvinist upbringing, debates over free will, and experiences with addiction and recovery, emphasizing surrender and Simone Weil’s idea of curing faults by attention rather than will. *unSILOed Podcast is produced by University FM.* Episode Quotes: AI and the new disenchantment 03:42: I think the whole idea of disenchantment is that we can understand the world, right? That we have like, the more we gather more information, more data, we're slowly gaining more control and more understanding. And now we find ourselves at the mercy of these systems that are, in some ways more intelligent than humans, that are better at predicting things than humans, that are outsmarting humans already in many ways. And we don't understand, even the people who are making them don't totally understand how they work. And we're at a point of information glut and overload where we almost have to defer to these opaque systems in order to understand the world. And I was curious about the idea of like, well, how is it different to, just have to accept an algorithmic output on faith as opposed to what I was told as a Christian, which is like, “The world is so complex we can't understand it, we just have to trust God and His will.” Why we see ourselves in AI 06:16: “I think that we are kind of doomed for better or for worse to seeing the world through the lens of the human. And the fact that we do this with... really crude technologies that we tend to personify. And then here come these algorithms that use language, and we have never in our human history encountered something non-human beyond a spiritual being, that uses language and interacts socially with us in that way. And I just think we're not prepared evolutionarily, to engage with that kind of technology without imbuing it with personhood. When metaphors stop being metaphors 10:50: In the earlier days of AI research, it was really common to see words like thinking or learning in quotation marks, just to signal that these were metaphors, and at some point, we lost those quotation marks, and in fact, now a lot of people will say, "Well, they are thinking. They are learning. Like, what's the difference?" And so yeah, I think we're never going to get away from metaphors. Like, our whole language is built on metaphor, but, do think there's a way in which, it does make a difference whether you're attentive to when you're using a metaphor and when you've, it's become a dead metaphor and you've forgotten it. Show Links: Recommended Resources: The Protestant Ethic and the Spirit of Capitalism Transhumanism Ray Kurzweil Simone Weil Akrasia Reformed Christianity Julian Jaynes Iris Murdoch Arthur Schopenhauer Saint Augustin Bill W. Amor Fati Guest Profile: Meghan O’Gieblyn’s Website Wikipedia Page Guest Work: Harpers Articles Amazon Author Page Will and Attention: A Memoir Miss MacIntosh, My Darling God, Human, Animal, Machine: Technology, Metaphor, and the Search for Meaning Interior States: Essays If you enjoyed this show, here are some other unSILOed episodes you may like: 649: N. Katherine Hayles - Bacteria to AI: Technics, Nonconscious Cognition, and Meaning in LLMs Christine Rosen Sherry Turkle Clancy Martin

Oct 16, 2026

Nir Halevy is a professor of Organizational Behavior at the Stanford Graduate School of Business, and the author of the new book called Level Up: Why Hierarchies Are Broken and How to Fix Them.

Oct 13, 2026

Why is it easier to imagine the end of the world than the end of capitalism? Believe it or not, the economic system was not inevitable in human history, and it’s not inevitably in our future either.

Oct 9, 2026

What happens when your brain predicts a symptom that doesn't belong — and your body obeys? Can a diagnosis itself make you sicker? And could the way your doctor delivers bad news change the course of your disease?

See all episodes →