What to Do When the Boss Is Wrong

“Nobody disobeys my orders,” the president insisted. But workplaces function better when they make room for defiance.

White House Counsel Don McGahn sits behind President Donald Trump at a Cabinet meeting in the White House.
Jonathan Ernst / Reuters

Mercurial bosses in dysfunctional offices sometimes give orders that their employees just ignore—even when that dysfunctional office is the highest in the country. According to Robert Mueller’s recent report, Donald Trump tried to get his staff to impede the special counsel’s investigation, but figures such as Don McGahn and Rod Rosenstein protected the president—and themselves—by quietly letting those orders slide.

In better-run offices, employees defy their superiors overtly. Back in the early 1980s, when Joanna Hoffman was in charge of marketing for Apple’s nascent Macintosh computer system, her boss, Steve Jobs, was a demanding, tantrum-throwing perfectionist. According to his biographer, Walter Isaacson, every year from 1981 on, the team developing the Mac gave an award to the person who could best stand up to Jobs. The first winner was Hoffman.

At one point, Isaacson wrote, she found out that Jobs had adjusted her marketing projections “in a way she found totally reality-distorting.” As she marched toward his office, she told his assistant, “I’m going to take a knife and stab it into his heart.” The company’s counsel overheard her and rushed out to stop her. “But,” she told Isaacson, “Steve heard me out and backed down.” The next year, she won the award again.

In the traditional workplace hierarchy, CEOs are used to getting their way, and open defiance could endanger a worker’s job. The literature of human-resources management abounds with articles such as “How to Write Up an Employee for Insubordination” and “Getting Compliance When Employees Simply Do Not Want To.” Tips to employees on how to fend off unwise, unethical, or even illegal demands from above are harder to come by.

A product of the business world, Trump couldn’t abide the notion that his underlings would question him—even after Mueller noted that, in slow-rolling his demands, they’d limited his exposure to obstruction-of-justice charges. “Nobody disobeys my orders,” Trump insisted.

The best bosses, however, recognize that defiant employees are sometimes right and that, even when they’re not, their disagreement is useful. In 1985, when Jobs was fired from Apple and started NeXT, Hoffman went with him. Some firms, as a matter of policy, urge employees to speak up. McKinsey, the management-consulting firm, insists that employees have an “obligation to dissent.”

Workplaces function better, business ethicists point out, when they make room for a certain amount of defiance. “I think you always have to make independent judgments about orders that come down to you,” Charlan Nemeth, a psychology professor at the University of California at Berkeley, said in an email. Nemeth, the author of the 2018 book In Defense of Troublemakers, added, “People who speak up are often those most loyal to the organization.”

You’d be hard-pressed to find a psychologist or organizational-culture expert who endorses the idea of blowing off your boss’s commands and hoping she won’t notice. And in the face of real wrongdoing, outright defiance is a clear moral mandate. This is why we make movies lionizing whistle-blowers, and why protections for them are enshrined into law. In military courts, the refusal to carry out an unlawful order is protected. Indeed, it isn’t defined as insubordination at all.

Most of the time, though, the modern workplace can be a difficult venue for conspicuous displays of individual conscience. Activities that are protected by law—for example, union organizing—are often strongly discouraged in reality. Even under the most genial of bosses, office politics usually favor collegiality and compliance over overt confrontation. Some corporate boards, Nemeth notes in her book, even include “team player” clauses in their contracts, discouraging members from disagreeing. Ultimately, what constitutes insubordination is in the eye of the person who can fire you for it.

Even when the boss isn’t fudging numbers or trying to subvert a federal investigation, organizations are worse off when employees defer too much to those in charge. Entrepreneurial history is littered with examples of executive autocracy, from Henry Ford to Abe Rosenthal of The New York Times. It’s also littered with examples of when that style failed. The “cult of the CEO” that took hold in the 1980s and ’90s flattered top executives into equating their companies’ best interest with their own self-aggrandizement. The hardest-charging corporate chieftains may get their comeuppance quickly—for instance, Albert “Chainsaw Al” Dunlap’s infamous stewardship of Sunbeam in the 1990s resulted in his firing amid an accounting scandal after just 23 months—but not before doing great harm to the companies they lead. Sunbeam declared bankruptcy a few years later.

Especially in such environments, disagreement helps everyone make better decisions. “The beauty of the results of our decades of studies is that, even if you are wrong, your dissent stimulates others to think in more open, more divergent, and better ways,” Nemeth said. “They consider more information and alternatives, more cons as well as pros of a position, and in general the team will make better decisions.”

Other studies suggest that employees will perform better when given moral autonomy than when they’re just expected to obey. In 2018, the Harvard Business School behavioral scientist Francesca Gino and her colleagues conducted an experiment: They posed difficult ethical challenges in which there appeared to be no good solution. They then asked some participants what they should do and others what they could do. The “could” group generated more creative solutions, Gino said via email. Gino, the author of the 2018 book Rebel Talent: Why It Pays to Break the Rules at Work and in Life, also cited research indicating that when we experience conflict, we generate more original solutions to problems than when we are in a more cooperative mood.

In other words, confronting the boss is fundamentally helpful. Even when an employer’s order crosses no ethical boundaries, Gino said in a subsequent message, “it could still mean carrying out a process that could be better if employees asked questions rather than simply accepting blindly what they have been asked to do.”

That’s why Joanna Hoffman rejected Steve Jobs’s fanciful marketing projections. She survived because Jobs was, at least sometimes, willing to admit when he was wrong and his subordinates were right.

Good leaders understand how important that capacity is. “Put simply,” the author and entrepreneur Bill Taylor wrote in Harvard Business Review, “you can’t be an effective leader in business, politics, or society unless you encourage those around you to speak their minds, to bring attention to hypocrisy and misbehavior, and to be as direct and strong-willed in their evaluations of you as you are in your strategies and plans for them.”

That kind of humility is in short supply among many CEOs (including, he’s suggested, the head of the country). Taylor pointed to the work of the retired MIT management professor Edgar Schein, who warned, “Deep down, many of us believe that if you are not winning, you are losing.” Sound familiar?

Whether those people who directly disobeyed, blew off, or just creatively interpreted Donald Trump’s orders did the right thing remains to be seen. After all, they were the ones who stood between him and a much stronger case for criminal wrongdoing. What’s undeniable is that, in government and the business world alike, insubordination has its uses—not the least of which might be protecting the powerful from themselves.