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A leading constitutional lawyer shared surprising advice for companies anxious about Trump’s anti-DEI hit list

By
Lila MacLellan
Lila MacLellan
Former Senior Writer
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May 20, 2025, 11:19 AM ET
Legal scholar Kenji Yoshino speaks on stage
Kenji Yoshino asked companies to think twice before jumping into negotiations over legal DEI practices. Kristy Walker/Fortune

One of President Donald Trump’s earliest anti-DEI executive orders took aim at private-sector companies and organizations, instructing the heads of federal agencies to list those they consider the “most egregious and discriminatory DEI practitioners” so the companies might be investigated for “civil compliance investigations.” The order set a 120-day deadline for the alleged offenders to be named.

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That was four months ago. In other words, the deadline for this executive order is upon us. Right now, it’s unclear whether the government’s list will materialize on time—or at all—but companies are preparing just in case. 

As they do, Kenji Yoshino, a top legal scholar and a professor of constitutional law at the New York University School of Law, has some advice: If you find your company is on the list, don’t negotiate, he says, “unless you have your eyes wide open to the fact that this is not going to end.”

Negotiating may look like a way to escape a prolonged legal battle, but it will only identify you “as a soft target for more negotiation,” Yoshino told the audience at Fortune’s Workplace Innovation Summit conference on Monday. 

An ‘insightful’ memo

His suggestion was inspired by an “insightful” open letter written last month by Sheila Heen, a Harvard Law School professor and deputy director of the Harvard Negotiation Project, Yoshino also said. Heen’s six-page missive, which was widely shared on social media, urged U.S. law firms under pressure from Trump’s White House (ostensibly over DEI and pro bono practices) not to negotiate with the president. Although much of Heen’s memo is specific to legal services and the way law firms operate, her underlying rationale is applicable no matter what type of business or individual is weighing their options.

Heen explained in her memo that her “don’t negotiate” advice drew on her years of experience. She is also the co-author of Difficult Conversations: How to Discuss What Matters Most, a best-selling book first published in 1999. “I have been teaching negotiation at Harvard Law School, and developing theory and practice at the Harvard Negotiation Project for thirty years,” she wrote. “I have spent my career helping colleagues and combatants find common ground. I’ve worked in international ethnic conflict, with senior teams across industries, and with judges, law firms, and general counsel offices. I’m now offering advice that I almost never give. Do not negotiate.” 

To unpack her reasoning, Heen also explains a foundational truth about what drives people in deal-making. “Negotiators can be driven by any of three approaches: interests, rights, or power,” she writes.
The first category is self-explanatory: People come together to work out an agreement that best serves the parties’ priorities.

“A rights focus looks at what parties are due based on industry practices, or under legal, moral or human rights principles,” she adds, while those who are motivated by power use their authority to wield it, while “weighing the strength of the other side’s alternatives away from the negotiation table.”

Agreements centered on balancing interests and respecting rights can be productive and “stable,” she says. However, Heen continues, “President Trump is a caricature of a unidimensional negotiator, operating exclusively from the domain of power. He rarely appears to care about the issues at hand or the people directly or indirectly affected by his actions. He tramples on rights–human rights, due process rights, constitutional rights–willy-nilly.”

“Oft-described as a schoolyard bully,” the memo continues, “Trump’s attacks on law firms are not about DEI and pro bono hours any more than the playground shakedown is about the lunch money.”

Heen also explores what could happen when companies signal they’re open discussions with the president. “The hope is that the President’s attention moves on to other firms and players, and you live to fight another day,” she begins. Instead, she continues, you are likely to encounter ongoing threats and “meddling.”

“While the agreements may attempt to preserve your ability to say no at any point in the future,” Heen adds, “the President’s reaction to that perceived betrayal may be even worse than the original sanctions.” 

Another piece of wisdom: “[C]onceding anything to the administration teaches Trump that, Yes, maybe he can push you around. Coming to agreement confirms it: you are willing to sign over your autonomy
and let him micro-manage the internal decision-making and governance of your firm.”

The price is higher than you think

On stage, Yoshino described a similar danger for blacklisted companies who might attempt to negotiate.

“What organizations often think is, ‘Oh, it’s just $100 million or so, and that’s a very low price to pay, relatively, for getting off of this blacklist or getting out from under the crosshairs,’” he said. But in reality, the cost is going to be $100 million plus future demands, “plus all the negative press and backlash that you’re going to get from the other side,” he said, referring to the pro-DEI movement. 

Yoshino emphasized that he wasn’t suggesting that negotiating is always the wrong move—he simply wants companies to be aware of all the possible risks connected to it. Namely, that the dealmaking will never end. 

Read Sheila Heens’ full memo here; watch Fortune’s interview with Yoshino, here.

Join us at the Fortune Workplace Innovation Summit May 19–20, 2026, in Atlanta. The next era of workplace innovation is here—and the old playbook is being rewritten. At this exclusive, high-energy event, the world’s most innovative leaders will convene to explore how AI, humanity, and strategy converge to redefine, again, the future of work. Register now.
About the Author
By Lila MacLellanFormer Senior Writer
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Lila MacLellan is a former senior writer at Fortune, where she covered topics in leadership.

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