The Worst Bosses in Film

They say that art reflects life, and when it comes to how we perceive our workplaces, this is often true. Though the situations portrayed in film are often exaggerated (few of us would plot to kill our boss, however often we may dream of their demise), movies and TV shows about workplace dynamics can sometimes be very truthfully reflective of the challenges we face, both as employers and as employees. Here, we take a look at what some of the most notorious bosses in film teach us about what not to do.

The “I Own You” Boss

This is the boss that usually takes the crown when it comes to horrible bosses. They are perfectly willing to ruin your life to get what they want and they expect you to be grateful for letting them do it. Think: Buddy Ackerman (played by Kevin Spacey) in Swimming with Sharks or Miranda Priestly (played by Meryl Streep) in The Devil Wears Prada. These bosses feel it is their prerogative to make unreasonable demands of their underlings and think it is unreasonable for those underlings to be anything but delighted to serve them or anything but brilliantly successful in attending to their boss’s needs (or whims).

The Devil Wears Prada (2006), 20th Century Fox

These tyrants often believe, or at least profess to believe, that it is good for their subordinates to be exposed to this kind of treatment in order to “toughen them up” for work in one or another tooth-and-nail industry. They are permitted to persist in their tyranny because they are, when it comes down to it, very good at their jobs and underlings put up with it because it does a career good just to be working in their shadow.

But this can’t be the only way. As unforgiving as these fields may be, the dog-eat-dog cultures in these industries persist because they are allowed (and encouraged) to persist by those at their pinnacle. As other industries, i.e. those related to technology, look to raise productivity by raising the quality of life of their employees, it may be time for industries traditionally ruled by iron fists to reconsider whether they are likely to attract the best talent with the old autocratic approach now demonized rather than admired in film.

The Unforgiving Perfectionist

Perhaps most closely related to the “I Own You” boss is the unforgiving perfectionist. Like Miranda Priestly and Buddy Ackerman, this boss is a tyrant. But unlike them, there is no carrot of career advancement buried under the heel of their boot. This boss rules only through fear and threats. We see a version of this boss in David Harken in Horrible Bosses (another sadistic tyrant played by Kevin Spacey…hmmm), but we think this more classic example really highlights the nature of this approach to management.

Star Wars: A New Hope (1977) and The Empire Strikes Back (1980), Lucasfilm and 20th Century Fox

In Darth Vader, we see tyrannical management taken to its extreme. Not only does failure result in very literal termination, his expectations, like those of the boss who thinks they own you, are largely unreasonable (“Asteroids do not concern me, Admiral. I want that ship, not excuses…”). This boss has no interest in his underlings’ success or failure and is happy to move through subordinates (and coworkers) until he happens to come across one lucky enough to stumble upon a route to his end goal – a goal which he can’t be bothered to share with those he expects to help him reach it.

This “leadership” style is, besides of course being morally detestable, totally unsustainable. With no promise of reward, employees will do only what they have to in order to avoid punishment. If demands are too high, they get burnt out quickly and will eventually get wise and realize they can find other jobs, appeal to law and workplace regulations, or join the rebel alliance to get out from under the threats of their bosses. In a workplace ruled by a tyrant, it only takes one savvy employee to remind the others of their rights as workers. It is too fragile a system to be maintained in most modern workplaces, and one condemned by management experts and labor laws alike.

The Boss Who Has No Business Being the Boss

This may be a boss with no managerial skills, no knowledge of the industry, no interest in being a leader, or someone who simply isn’t competent enough to take on a leadership role. In movies, we most often see these bosses pop up when an undeserving heir takes over their parent’s company and is so caught up in their newfound sense of power or access to wealth that everyone in the company – and the company itself – suffers.

Horrible Bosses (2011), New Line Cinema

Though the business world is certainly rich with inept heirs, in real life, an incapable boss is more often the result of unqualified managers get promoted to their point of incompetence, a phenomenon commonly referred to as the Peter Principle. In these cases, an excellent salesperson, for example, may be promoted to regional manager as a reward for success in sales, regardless of whether his or her strengths include qualities necessary to a capable manager.

While this tendency has been well-known in the management industry for decades, it is still not uncommon to see successful individuals promoted to the point at which they fail. Managers, then, must be careful to nurture those who may lack the skills to take on a job for which they may be “next in line”, to recognize in themselves areas of expertise that they may need to strengthen in order to fulfill their current roles, and to recognize when the necessary skills or abilities are not likely to be developed – in themselves or others – and find other ways to reward excellent performance.

The Passive Aggressive Boss

The passive aggressive personality rears its head everywhere, but it is perhaps nowhere more irritating than in the workplace. The passive aggressive boss avoids confrontation at all costs. They send memos instead of making direct requests; they frame bad news and unfair decisions in language that is difficult to oppose; they hide behind company policy and pass the buck in order to avoid taking responsibility for unpopular decisions. Their passive, “everything’s fine” demeanor leaves employees feeling not only disempowered and taken advantage of, but ultimately resentful and just plain annoyed.

Office Space (1999), 20th Century Fox

Employees will not respect the passive aggressive boss and will always be looking for a way to get out from under them. Because passive aggression is a form of manipulation – one that can easily devolve into sabotage – once it is introduced into company culture, cohesion and morale quickly break down. The result? Attrition and high turnover at best, backstabbing and deliberate undermining at worst. Better to engage with employees directly, listen to what they have to say, and address their concerns. Lance the boil instead of letting it fester and infect the body.

The Best Buddy

This unfortunate soul is trying at once to be everyone’s best friend and to be everyone’s boss. Usually driven by insecurity – either in themselves or in their position – their primary concern is to be well-liked, which means, among other things, avoiding confrontation, letting poor performance slide, and allowing laxity to go unchecked.

The Office (2001), British Broadcasting Corporation (BBC)

While opinions vary on how friendly relationships between supervisors and employees should be, it is fairly certain that a boss who is more concerned with gaining his or her employee’s approval than with running an efficient or productive office is not likely to succeed in either. Add to this the often inappropriate familiarity that can arise as superiors try to forge unnatural friendships with those working for them, and the result tends to be a lack of respect for the boss, a lack of motivation on the part of the employees, and a deterioration of productivity in the absence of any real leadership.

The “Everyone Should Be My Clone” Boss

This type is also known as the “Know-It-All”, and it is not confined to bosses. It is, however, especially unappealing in those in positions of authority. Here, we have an individual who attempts to motivate employees by highlighting his own accomplishments, setting himself as a standard to which subordinates should aspire.

Glengarry Glen Ross (1992), New Line Cinema

The obvious arrogance of such an approach aside, the end result is more often to demoralize those to whom the self-aggrandizing diatribe is directed than to inspire them to comparable greatness. Employees have likely already taken note of their superiors’ accomplishments. The desire for similar rewards is, indeed, often why they have chosen that work in the first place.

For the majority or employees, such reminders only serve to highlight a hierarchy which, in many cases, they perceive as working against them. It may also remind them of their own failings or, as in the case cited above from Glengarry Glenn Ross, engender resentment at what they feel is an unfair distribution of opportunity or reward. It is only the very rare employee who believes that their failure to achieve the success equal to that of their superiors results from their own lack of ambition or hard work. The boss who thinks everyone should try to be like them is, by definition, failing to recognize and encourage the strengths of his or her subordinates.

The Unscrupulous Boss

This character, in film anyway, tends to be primarily cast as middle management. This is the supervisor whose primary goal is to work his or her way to the top of the food chain. But by “work” here is really meant lie, cheat, and manipulate, most often at the expense of subordinates. While we may have come to expect this behavior in our politicians, the effects of this kind of scheming in the workplace can be disastrous.

9 to 5 (1980), 20th Century Fox

If a manager’s primary motivation is their own glorification, they will not only be willing to sacrifice the well-being of the employees that make a company productive and profitable, they will likely be willing to sell out the company itself, should a more prestigious or lucrative opportunity present itself. This sense, combined with the knowledge that the accomplishments of the team are likely to be appropriated by the boss as personal achievements, leaves subordinates feeling insecure and unmotivated, resulting in a lack of company loyalty, reduced productivity, and high turnover.

Other bosses to look out for:

Jekyll & Hyde

This is the superior who treats you like the most valued employee one minute, then berates you and threatens your job the next. One day, you’re rewarded for taking initiative, another you’re chided for acting out of turn. Trying to figure out how to please this kind of boss can end up taking an employee’s attention away from their real task – to contribute to the success and profitability of the department and the organization. It should always be clear to employees what is expected of them and how they can succeed, and the expectations of their superiors need to be consistently in line with these standards.

The Ghost

We rarely see this boss in film because, well, we rarely see this boss. This is because they are out on business trips, at conferences, or schmoozing clients at lunch the majority of the time. On the rare occasions they do make an appearance in the office, they are in meetings or on the phone with the door closed, inaccessible to their team. It is, of course, inevitable that some positions require those who fill them to be out of the office a great majority of the time. However, if travel or meetings mean that someone in authority will be largely inaccessible, then someone who is accessible needs to be placed in a position to act on their behalf or at least be able to communicate quickly and consistently with the actual boss. Otherwise the result is a leadership vacuum inside of which employees may start to form their own agendas and the unified vision of the company will get lost.
Of course no boss is relegated to just one cardinal sin of management, and few embrace any of them fully, but being aware of these tendencies and traits can help managers to check their own behavior as well as promote to positions of authority those who are well-suited to lead the team.

Film clips used in accordance with the Fair Use statutes of U.S. copyright law.

The original post was published at Find My Shift.

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Abbie Reedy is “The Conjurer of Content” at Heroic Search, a Search Engine Marketing company focused on ROI and committed to making the Internet a better place.