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.