Published on: September 29, 2026 at 10:28 am
Many CEOs have asked themselves, “Is there a secret to staying on U.S. President Donald Trump’s good side?” Some have publicly embraced him, including prominent tech CEOs, while most have stayed silent. Only a small minority have opposed him.
According to Academy of Management Scholar Jeffrey Sonnenfeld of the Yale School of Management, who moderated the panel “The Framers of 1776 vs. The Nation’s Leadership In 2026; Is the Vision Now Vivid or Blurred?” at the 2026 AOM Annual Meeting in Philadelphia, many chief executives participate in The Business Roundtable, but the organization has not taken a public stand with regard to the Trump administration. Sonnenfeld has coauthored the book Trump’s Ten Commandments: Strategic Lessons from the Trump Leadership Toolbox with Steven Tian, also of Yale.
The CEO of a popular U.S. motorcycle manufacturer responded to Trump’s tariffs from a purely financial perspective but still drew the president’s ire.
“What could be a more iconic U.S. brand than Harley-Davidson?” Sonnenfeld said. “Trump attacked the CEO of Harley-Davidson, Matt Levatich, in 2018 after the company announced plans to shift some of its motorcycle production overseas to avoid retaliatory EU tariffs—his hand was forced because of reciprocal trade tariffs blocking the sale of bikes, which were 100% made in the U.S., in the EU market.”
Levatich “had to shut down a plant in Kansas City and open one up in Thailand, and Trump was furious—he took it personally,” Sonnenfeld said. Trump “told people not to buy Harleys. Harley drivers lean a little MAGA and coincidentally Harley workers lean a little bit anti-MAGA, but this CEO is nonpolitical—he just wanted to pilot this company down the center of the road, but he winds up being a target of political vitriol.”
“The stock plummets, and he gets fired, so there’s a cautionary tale.”
Sonnenfeld said that unity is the only way for CEOs to get President Trump to back down.
“You have to have collective action, but just calling him names from the sidelines doesn’t do it—you can’t fire back verbally the same way he does,” he said. “That old saying holds true in this case: ‘Don’t get into the mud pit with a pig and start throwing around the mud because the pig knows it better than you do and enjoys it.’
“Senior business executives have realized that they need to take the high road with the president, who sometimes will listen to reason,” Sonnenfeld said.
“When Tim Cook, the CEO of Apple, brings a little gift, it’s not a big extortion payment,” he said. “Michael Dell, or especially Arvind Krishna, the CEO of IBM, and other tech titans will meet with him to discuss American technological dominance, AI, quantum computing, and things like that.
“I’m not defending the oligarchs like Elon Musk and Mark Zuckerberg and Jeff Bezos and others; these people have dominant control of their companies, but the other people who are salaried hired hands, whether it’s tech titans or retailers or pharma CEOs, when they meet with Trump privately to talk through the issues, they’ve often made some headway,” Sonnenfeld said.
“So, CEOs have come to the conclusion that there’s no need to humiliate him, at least while he’s still president—we’ll have him at the helm for at least another two years. So how do you successfully navigate the rest of his presidency without losing your job or hurting your company?”
