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Have You Encountered One of These 4 Difficult Boss Types?


Thu Mar 21 2019

Have You Encountered One of These 4 Difficult Boss Types?

As a corporate trainer and professional speaker, I speak on various topics (such as communications, meeting facilitation, team development, and project management) to a variety of different audiences across the country and beyond. Over the past few years I’ve noticed something that stops me in my tracks every time it happens. Invariably, during my Q&A after my talk (irrespective of the talk topic) one of the first three questions is, “But what if the problem person is my boss?” This insane consistency just reminds me that the idyllic, inspirational, supportive manager is in many ways the mythical creature of our time. Instead, most of us find ourselves struggling to succeed in spite of our boss, not because of our boss.

In defense of bosses everywhere, part of the problem may be that expectations are not always realistic. I think that bosses are like doctors in that patients walk in with the completely erroneous assumption that just because someone has an MD behind their name, they’re all-knowing and all-powerful—and this simply couldn’t be further from the truth. There are great doctors and horrible doctors, and the same is true for managers and executives. Unfortunately, too many of us get stuck with the difficult boss. The good news is that you really can manage up, and not just succeed in spite of the difficult boss . . . but maybe teach them a thing or two in the process and earn their respect!


Clearly, there are many permutations of the difficult boss; however, the following four types seem to appear with unsettling frequency.

The Tornado

“I hope you don’t mind me intimidating everyone with my overbearing nature at your team meetings . . . I’m just trying to help you speed things along.”

Sometimes our boss can become the “problem participant” in our meeting, and that can be difficult to manage.

The Wishful Thinker

“Would you please boil the ocean, and solve world peace too while you’re at it?”

We’ve all encountered the boss who expects you to achieve the impossible. They somehow think you’ve got a magic wand tucked away in your cubicle and can move mountains. When you encounter this boss, don’t fall into their haze of wishful thinking.


The Clueless Chameleon

“I’m not exactly clear on what I’m looking for, but I’ll be sure to hold you responsible when I don’t get it.”

Too often, bosses may have a vague idea of what they want; or worse, they may keep changing their mind. When this happens, employees are sent on wild goose chases trying to reach a loosely or poorly defined objective. Don’t fall into that trap.


The Naked Emperor

**“I love the sound of my own voice in particular, because my ideas are brilliant!”

Nothing is more frustrating than a boss who sees only what they want to see and appears blind to reality (particularly when that reality may reflect poorly on them in some way). This type of boss is particularly dangerous because their blind spots could certainly derail your success if you become too closely associated with them and they go down in flames. Don’t blindly go along.


If you sense that your work environment or boss is a sinking ship, get off! At least build a broad network and develop a Plan B in case they are demoted or removed from the organization. Managing up means using techniques to help your boss (and yourself) be as successful as possible in spite of potential personality differences or shortcomings.

This video provides valuable tips on managing difficult boss personality types.

Want to learn more? Join me at the ATD International Conference & Exposition for the session, The Unwritten Rules of Managing Up: Surviving the “Difficult Boss” (and Thriving).

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