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featuresThe go-to guy for CEOsJeffrey Sonnenfeld helps leaders learn from their peers. Debra Spark '84 is a professor of creative writing at Colby College. Her most recent novel is Discipline. The dress code said business casual, so it was the usual: suits or suit jackets, some dresses, sober colors, and the occasional bulletproof vest. The group of 200 consisted of CEOs from corporations like IBM, Merck, Otis Worldwide, and Nordstrom, along with past and present federal officials, high-level economists, academics, and broadcast and print media leaders. In January, Sonnenfeld was back in New Haven, this time with a group of about 70 university presidents, talking about the growing lack of confidence in higher education. They talked about tuition costs, concerns over how college prepares students for the workforce, and the political climate on campuses. Leaders agreed that there needs to be a clearer narrative on the actual “return on investment” of college and about higher ed’s important roles in society: preserving democracy, ensuring fairness, spurring economic growth, and enhancing the earnings and well-being of graduates. On the question of institutional neutrality—a policy being adopted by some university leaders in the wake of controversies over Israel and Palestine—some confessed to wanting to keep their heads down to avoid attack, while others emphasized the need for “moral clarity” in deciding when and when not to speak. At both events, the only time Sonnenfeld contradicted an opinion was when someone at the CEO Summit said the problem with our current society was education. Which isn’t to say that Sonnenfeld is shy about his own opinions. Even as he was posing questions to university presidents, Bloomberg, CNN, Reuters, and Business Insider were reaching out to him to comment on corporate DEI policies, CEOs who court Trump’s favor, and the Russian economy. In a typical year, he publishes, alone or with associates, about 100 op-eds, and he appears frequently on news networks like MSNBC or CNBC to offer commentary on topics ranging from the top CEOs to watch in 2025 to Fortune 100 leaders’ pre-election lack of support for Trump to the possible domino effect of the fall of the al-Assad reign in Syria. Born near Philadelphia to a mother who immigrated from Russia and a father who owned a clothing store, Sonnenfeld took on adult responsibilities early, in part because of his parents’ serious health problems. “While they were sometimes both in the hospital, I was there closing out the store and trying to count up the cash at the night and pay people,” he says. Around 11 pm, he’d start his homework. “I was doing that out of necessity but I liked it.” He entered Harvard in 1972, thinking he’d be a doctor, but he blossomed far more in a course called “Human Behavior in Organizations” than in organic chemistry. On graduating, he decided to simultaneously pursue an MBA and DBA, also at Harvard. “When I’d get tired of the venal world of the MBAs, where they were trying to figure out how to take the pennies out of each other’s penny loafers when they weren’t looking, I would identify as this cerebral academic,” he remembers. “But then I’d get tired of the whining, graduate student Marxist views of entitlement, and I’d think, ‘At least these MBAs are having an impact. They’re not just on the sidelines.’ I was really interested in life stages, but also interested in ethical social impact, responsible governance. I figured, well, I’ll just do them both.” Sonnenfeld taught for nine years at Harvard Business School. When his 1988 book on executive succession, The Hero’s Farewell, became a bestseller, people suggested he create “a school for the boss,” as he puts it. So he did, starting at Harvard then bringing the forum with him to a professorship at Emory and later to Yale, where he has been since 1999. And why has he remained interested in educating CEOs? “You know that old Greek adage, how the fish rots at the head?” Sonnenfeld said recently in his SOM office, a cluttered room that he describes as looking like an “OSHA hazard.” If leaders “don’t get timely feedback, it cascades down on the hierarchy and the whole firm. All the employees suffer. Employees aren’t the only people who should learn from feedback, and you aren’t going to get challenging feedback from a lot of lieutenants that feel beholden to the boss. They’re afraid of vindictiveness. If you can imagine that.” If it is indeed lonely at the top, the peer-to-peer nature of the gatherings gives leaders something they are not getting back at work, which appears to be why they routinely take an entire day out of their busy schedules to attend. Bob Diamond, former CEO of Barclays and current CEO of Atlas Merchant Capital, has been to 30-plus summits and notes Sonnenfeld’s gift for “creating a platform where people are comfortable saying what they believe as opposed to what they’re supposed to say.” Lynn Tilton ’81, CEO of Patriarch Partners, who has also attended at least 30 summits, describes Sonnenfeld as “brilliant in his counsel, courageous in his stance, trustworthy in our confidences, and unwavering in his friendship.” Though other organizations now have CEO programs (many with Sonnenfeld advising on the launch), gatherings like the World Economic Forum at Davos or those through Forbes, Fortune, and Businessweek are, according to Sonnenfeld, “gabfests with a commercial agenda.” Not Yale. “We don’t have a political agenda. It’s completely non-commercial.” It is not a place for self-promotion. Instead, Sonnenfeld and his team “research the hell out of the companies” and then “surface their setbacks.” Not to shame, but to challenge and probe, to see what can be learned from trouble as well as achievement. From his 20s on, Sonnenfeld has been interested in the topic of his graduate school thesis (and the title of his first book): Corporate Views of the Public Interest. That subject has recently been refined, for Sonnenfeld and those he educates, into the question of how and when one should undertake a collective rather than individual corporate response to societal troubles. Days after Trump’s 2025 inauguration, Stephen Henriques ’21MBA, CELI’s senior research fellow and one of Sonnenfeld’s frequent coauthors, acknowledged that there was no easy answer, saying, “It’s knowing when the right moment is. When a president’s issuing an executive order, what can a CEO do then? When somebody’s challenging the foundation of democracy, as in 2020, that’s when somebody needs to speak up.” Weeks later, Henriques and Sonnenfeld felt it was the right moment. They wrote in a New York Times op-ed in March that “American companies spent decades developing multinational operations relying on a web of economic trade agreements that fortified postwar America as the envy of the world.” Arguing that executive action was undoing all that and harming businesses and employees, Henriques and Sonnenfeld encouraged business elites to again speak as a collective. At a March CEO Caucus (attended by around 60 mayors, in addition to the CEOs), leaders spoke, again off the record, about their concerns and desires to apologize to international partners for their mercurial president. They said they would speak out if the stock market dropped 20 percent. When it dropped 16 percent they were, as Sonnenfeld was quoted as saying in the Wall Street Journal, “perilously close to hitting that tripwire.”
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