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7 Leadership lessons from Pop Culture’s Worst Bosses

These bad bosses may be fictional, but they deliver real-world lessons in leadership and management.

[Source photo: Macall B. Polay/HBO]

Warning: This piece has spoilers from television shows and movies, including The Office, The Devil Wears Prada, Succession, Severance, Working Girl, blackish, and Office Space.

Bad bosses. We’ve all had them. In fact, they’re so common that they’re regularly characters in the movies and television shows we enjoy. Their transgressions range from irritating annoyances to murderous intent, often with funny, horrifying, or otherwise compelling results.

Thankfully, most of us don’t deal regularly with felonious behavior in the workplace. But that doesn’t mean that bad bosses don’t create their own share of chaos. In a recent episode of The New Way We WorkFast Company Deputy Editor Kate Davis and speaker and author Diana Kander, host of The Growth League podcast, discussed how some common missteps and peccadilloes can undermine the work many people do to improve their leadership and management skills. Common issues like micromanaging, withholding honest feedback, and failing to deal with problem employees are behaviors of which many may be guilty from time to time.

So, we thought we’d take a look at some of the more well-known “bad boss” characters on television and in the movies to dissect their behavior to see if there were any takeaways. Turns out, leadership lessons are everywhere. Here’s what some of the worst screen bosses can teach us.


Bad boss behavior: Steve Carell played the leader of fictional Scranton, Pennsylvania paper company Dunder Mifflin for seven seasons. Michael Scott was needy and let his desperation for others’ approval, attention, and affection drive poor decisions and inappropriate behavior. This ranged from undermining employees’ opportunities for development and advancement to—in possibly his worst move—making a reckless and false promise to pay for low-income students’ college educations. It is only when Scott learns to be more confident in Carell’s final season that he fulfills some of his leadership potential.

The leadership lesson: People-pleasing clouds a manager’s ability to make the best decisions, especially when they may be unpopular. And when you don’t put faith in your employees and stay true to your word, it’s hard to cultivate one of the most important elements of leadership: trust.


Bad boss behavior: Rude, dismissive, and demoralizing, it’s hard to imagine why anyone remains working for this fictional fashion magazine editor-in-chief, played by Meryl Streep. Employees are expected to be on-call and work-life balance doesn’t exist in her world. Despite her dedication and loyalty, Andrea Sachs (Anne Hathaway) eventually walks away from the coveted role when she can’t stomach Priestly’s behavior toward loyal employees.

The leadership lesson: During Priestly’s more vulnerable moments, it’s clear that her behavior is driven by her own unrelenting perfectionism and the scrutiny she endures. What she fails to learn, however, is that if you don’t treat your employees with respect and give them a measure of work-life balance, you’ll lose your best talent.


Bad boss behavior: The patriarch of the Roy family, played by Brian Cox, is loyal to no one—not even the closest members of his own family, who are heirs to the family business. He seems to be preparing his adult children to take over his media empire, but his backstabbing and cruelty know no bounds. His behavior destroys his relationships and threatens the future of his company.

The leadership lesson: Mixing family and business can be tricky and requires clearly defined roles. (It also helps if everyone involved has even a marginally functional moral compass.)


Bad boss behavior: Despite promising her assistant, Tess McGill (Melanie Griffith), that she will help her climb the corporate ladder, Sigourney Weaver’s Parker instead steals her good ideas and tries to take credit for them. When the deception is finally revealed—as it so often is—Parker loses her job, and McGill gets the opportunity of a lifetime.

The leadership lesson: When you surround yourself with good people, recognize their ideas and achievements. Stealing ideas, lying, and taking credit for others’ work will quickly ruin a reputation.


Bad boss behavior: At Lumon Corporation, employees who work on the company’s most sensitive projects may elect to undergo the “severance” procedure, which blocks personal memories at the office and work memories at home. Cold and abrupt, Patricia Arquette plays Cobell, who oversees “severed” employees. But she also takes advantage of the memory lapse to insert herself into the life of employee Mark Scout (Adam Scott) as his neighbor and a lactation consultant to his sister. In a pivotal finale moment, the worlds collide and threaten the entire company.

The leadership lesson: Professional boundaries are important, even in seemingly friendly workplaces. Bonus lesson: brain surgery as a job requirement is probably a red flag.


Bad boss behavior: Lumbergh, played by Gary Cole, is the ultimate micromanager, sticking his nose into everything from how employees fill out forms to which office supplies they’re permitted to have. Instead of focusing on outcomes, Lumbergh keeps his employees where he can see them—even on their time off.

The leadership lesson: As Kander pointed out in The New Way We Work and a previous piece for Fast Company, micromanaging destroys innovation, curiosity, and a desire to move the organization forward. “The bosses that don’t recognize how they get in their own way, are getting the smallest amount from employees,” she says.


Bad boss behavior: Stevens, played by Peter Mackenzie, is a partner in the advertising agency where Andre Johnson (Anthony Anderson) works. He’s also a racist, although he doesn’t see himself that way. Stevens regularly drops microaggressions and biased remarks into his conversations. Johnson endures most of the remarks and often responds with quips, but occasionally, the behavior and comments become too much and lead to some of the show’s most insightful, moving, and provocative moments.

The leadership lesson: Racism and bias in the office reflect their presence as a whole. Only when they are recognized and confronted can leaders hope to create truly inclusive workplaces.

Perhaps the reason that the “bad boss” trope is so common in media is that employees weather so much poor leadership behavior. When we stop to question why an over-the-top depiction is funny or compelling, we may end up learning a thing or two about how to be better leaders in real life.


Gwen Moran is a writer, editor, and creator of Bloom Anywhere, a website for people who want to move up or move on. She writes about business, leadership, money, and assorted other topics for leading publications and websites. More

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