Jeffrey Sonnenfeld -Yale

From Harvard to Yale: Building the Premier CEO Education Institution

Jeffrey Sonnenfeld’s path to founding the Chief Executive Leadership Institute began with a book. His seventh book, The Hero’s Farewell, studied more than a hundred iconic leaders whose names had become synonymous with the companies they ran, from David Rockefeller of Chase Manhattan to Reginald Jones of General Electric, and examined how they left power. He mentions to us and in his book, four archetypes: monarchs who die in office or are removed by force, generals who reluctantly leave and often return like Bob Iger or Steve Jobs, ambassadors who transition into mentor roles, and governors who serve a bounded term and move on to something new. The book became a bestseller, and the conversations it sparked convinced him there was a need for a dedicated institution where CEOs could learn from each other as peers.

He pitched the idea to his then-dean at Harvard, where he had spent eighteen years, and was given a trial run. Here’s where the reboot moment occurred. But Harvard had a structural problem: having three CEOs on campus the same day was considered a scheduling error, because the institution was focused on fundraising and recruiting rather than making senior executives vulnerable as learners. Sonnenfeld believed deeply in the old Greek idea that people atrophy in high office and need constructive, critical feedback in real time. He took the Institute to Emory and eventually to Yale, where it has been based for nearly thirty years. Today it brings together CEOs from firms including Ford, UPS, Verizon, Pepsi, Dow, State Farm, Blackstone, IBM, Dell, and Morgan Stanley, among dozens of others.

The Room Where Egos Go to Learn

Getting a room full of the world’s most powerful executives to actually learn something is harder than it sounds. The instinct of every handler, lawyer, and communications director in their orbit is to prevent exactly that. Jeffrey Sonnenfeld has spent nearly thirty years dismantling that instinct one ballroom at a time. The formula sounds simple: no notes, no PowerPoints, no prepared questions, no stage, and no panels. What it produces is anything but simple. When the scaffolding of managed messaging gets stripped away and the people in the room recognize each other as genuine peers, something shifts. The heavily guarded executive who has not received an honest piece of feedback in years suddenly becomes a learner again. Sonnenfeld calls it “Treating them like playful porpoises instead of the scary sharks they actually are in the real world, and it works precisely because no one sees it coming”.

What separates the Chief Executive Leadership Institute from the many executive education programs that followed in its wake is the peer dynamic Sonnenfeld has spent decades cultivating. He researches every participant in the room before they arrive. The conversation is not scripted. There are no prepared questions. The format is designed to create the conditions for honest dialogue rather than managed messaging, and to generate the kind of constructive, critical feedback that CEOs almost never receive inside their own organizations. That feedback loop, Sonnenfeld argues, is what makes the Institute genuinely useful at scale, not just as a networking event but as a real learning environment for the people running the largest institutions in the world.

The Three Dimensions of AI for CEOs

When it comes to artificial intelligence, Jeffrey Sonnenfeld sees the challenge facing CEOs through three distinct lenses. The first is how CEOs are approaching the technology themselves. Three years ago, as large language models exploded into public awareness, the Institute began mapping the different tribes of CEO response. There were wild-eyed enthusiasts who embraced AI at all costs. There were resistors, including some tech pioneers, who warned of grave dangers ranging from job loss to the erosion of societal safety. There were executives who had no real idea what they were talking about but felt compelled to have a position. And then there was the largest group in the middle, trying to honestly assess where the value was and where the risks were in their specific industries. The Institute now has active research underway on agentic AI and how it plays out differently across sectors like healthcare and hospitality.

Beyond the C-suite, Sonnenfeld’s team has tracked AI legislation across all seventeen states currently moving bills forward, finding that Connecticut, Colorado, and California are the furthest along. One surprising finding is that existing consumer protection law already covers many of the intellectual property and privacy concerns that new legislation is designed to address, though areas like deepfakes and identity theft still need work. The legislative picture matters because the risks are real and moving fast, and most companies are not as far ahead of them as they think. On the educational front, Sonnenfeld believes the kind of teaching he does, spontaneous, associative, and drawing on decades of real relationships, cannot be replicated by any model currently in existence. But he is candid that AI has already produced work his team could not have matched on their own. A recent presentation built with AI-generated graphics for a group of agricultural cooperatives was, in his words, “Way better than anything they could have come up with themselves”. The lesson he draws is not that AI threatens great teaching, but that staying on your toes is no longer optional.

The Trump Leadership Toolbox: What to Learn, What to Avoid, and What to Understand-

Sonnenfeld’s latest book unpacks Donald Trump’s leadership style not as a simple endorsement or critique but as a three-part framework that he argues every executive needs. The first category is lessons leaders can genuinely emulate. Trump’s decisiveness and his impatience with bureaucratic friction are real advantages that large organizations consistently lack. His willingness to cut through the process and force a decision, even an imperfect one, is something many Fortune 500 CEOs could learn from.

The second category is lessons no leader should emulate. Trump’s approach to building trust, for example, is the inverse of what conventional leadership recommends . Where most trust-building starts small and accumulates over time, Trump opens with maximum pressure, a shock to the system designed to make everything that follows look reasonable by comparison. Sonnenfeld uses the analogy,  “Building a fire: you start with tinder, kindling, and small sticks before adding the heavy logs”. Trump skips straight to the heavy green logs. That approach may produce results in certain negotiating contexts, but for most executives, the conditions that work for Trump may not suit their leadership style. 

Sonnenfeld has known Trump since shortly after he bought Mar-a-Lago, and spent the first season of The Apprentice writing weekly leadership critiques for the Wall Street Journal. His verdict on the show’s premise was that it taught exactly the wrong lessons, turning leadership selection into an elimination game. While others may disagree, understanding different approaches help leaders come out better prepared.

China, Russia, and the Civic Duty of CEOs

Sonnenfeld played a central role in catalyzing what he describes “As the largest stampede of business exits in world history following Russia’s invasion of Ukraine, ultimately tracking more than 1,200 companies as they pulled out of the country”. His team of students worked around the clock to separate genuine exits from performative gestures, holding companies accountable for what they actually did rather than what they said. The financial results were clear: every company that pulled out benefited from it. The reputational and operational risks of staying outweighed the relatively modest revenues most of them were generating in Russia.

China is a different and more complicated challenge. He points to the pharmaceutical sector as the most urgent concern, noting that the US dependence on China for active pharmaceutical ingredients, including antibiotics, is far more dangerous than the dependence on Chinese textiles or consumer electronics, which can be sourced elsewhere. Companies like Apple, he argues, are doing a serious and genuine job of diversifying their supply chains, not just going through the motions.

His parting advice to the next generation of leaders returns to a theme he has spent his career championing. CEOs are not the only ones with a responsibility to speak out, but they are among the most visible. The instinct to hide behind institutional neutrality or to stay in a narrowly defined lane is, in his view, a failure of civic duty. That social capital, Sonnenfeld argues, “Is just as important as financial capital, and it is something every leader, not just CEOs, has an obligation to contribute”.