The Lighter Side

5 Types of Difficult Bosses

Yes, these lists are everywhere. I think Matt Groening wrote a “difficult bosses” series in his book “Life in Hell.” I’ve come up with my own list, however, that I think is actually reflective of what you may encounter in an office setting, plus some advice on how to deal with them. Enjoy!

1. The Avoider

Description: This boss is never around. He’s either out playing golf, on vacation, or has some sort of fancy remote-working environment that allows him a lot of time away from the office. It’s the kind of boss we all want to be, but to work for? That may be another story.

Pros: Very, very little micromanagement. If you are the independent type, you can expect to have plenty of leeway to get your work done. This is the ideal boss for you.

Cons: This is NOT a great boss for someone who needs direction, tends to ask a lot of questions at work and feels more comfortable with some guidance. If your avoider boss says to you, “Get x and x done, e-mail me if there is trouble”, doesn’t give you any parameters, and this strikes fear into your heart, you may want to consider working somewhere else.

How to deal with an Avoider: Make sure you are clear about his expectations of you. Never bug him relentlessly for details, because he doesn’t want to be bothered. He just expects his employees to get the stuff done efficiently with minimal supervision and interruption. If you really are lost, send him an e-mail asking him SPECIFICALLY what you need to know. This allows him to respond on his own time and thus, feel less like he’s being bothered by you.

2. The Micromanager

Description: One of the most common types of bosses you will encounter, the micromanager is a pain in the neck for anyone who has any ounce of self-direction. That includes you, for reading this blog. They constantly hover over you, making sure you are on top of every little minute detail of every aspect of your job. They’ll ask you to dot every “I” and cross every “T”, even when the “T” doesn’t need crossing. They’ll ask you if you changed the toner in the printer 15 times. The worst part is that they also tend to snoop and check what websites you have been visiting.

Pros: I suppose the micromanager could be good for an employee who is easily lost and needs direction on the job

Cons: They are irritating and will relentlessly hound you no matter how reliable an employee you may prove to be. You will actually do a WORSE job than you would have done on your own because it sure is tough to concentrate when someone is bugging you all the time while you are trying to work. They also have a tendency to talk to you while you are on the phone, making life at work even more challenging. Expect to have trouble focusing in general.

How to deal with a Micromanager: While this may be hard to believe, this may be the most dangerous of all the bosses in the long run. You can’t tell them to just go away and leave you alone, and your performance will likely suffer no matter what you do. They will make your job more stressful. One of the only methods that is effective in countering this type of boss is to be stubborn and ask a plateful of questions at once. Be confusing if you have to. Don’t fight back directly, but challenge them. If they ask why you didn’t do something, ask them why you should. The more questions you ask, and the more you are a pest back to them, the more they will leave you alone. Just don’t get yourself fired.

Or maybe, with this type of boss, do get yourself fired!

3. The Drill Sergent

785973_repressionDescription: This guy is old-school. He expects results, and he expects them without complaining. If you mess up, you’ll hear about it, and you will not be able to make any excuses. The drill sergeant is tough and can be mean. Does your boss actually yell at you for something small and insubstantial? Chances are good that you have a drill sergeant on your hands. They tend to be found more commonly in blue-collar settings than corporate environments, but they really do exist everywhere.

Pros: If you actually do a good job and follow orders, you’ll be rewarded. Generally these bosses have a sort of “tough love” thing going. They may even promote you if you can stand it long enough.

Cons: Ready to have a heart attack? Being yelled at/living in fear all day is hardly conducive to your health! It’s never a fun situation at work when you and all your co-workers suddenly grow quiet because the boss has walked into the room. Never. Note to the drill sergeant: this is actually not a good way to treat employees. Instilling fear will not lead to increased productivity. It will lead to employees quitting their jobs.

How to deal with a Drill Sergeant: If you are a sensitive person, just find another job. You are better off not dealing with this kind of garbage, no matter how much you are making, or how much you may like other aspects of your job. You may end up in the hospital. If, however, you have a tough skin (especially if you are used to the military) than become a model employee. If you stand out above your peers you’ll be treated better than the rest. Taking the blame for something that went wrong is actually a sign of strength, and the drill sergeant will respect you more for it. After all, they hate excuses. Just don’t screw up too much.

4. The Bum

Description: The bum will sit in his office all day playing online video games, sleeping, or on the phone with his friends. He never does any “work” at all, but somehow got into a position of power. Sounds like some politicians I know. He can be difficult in that his laziness is a detriment to your own job stability.

535904_sleepyPros: Usually the bum isn’t a difficult boss to work for. Since he has such low standards for himself, he isn’t usually too demanding. Expect to have a lot of free reign of your own.

Cons: It’s likely that your department (or even the whole company) may suffer due to your boss’ negligence over time. This could cause you to be laid off should the bum fail in his duties.

How to deal with a Bum: It’s not too hard at all. Prepare to come to work in a relaxed mood and ready to play minesweeper all day. As long as you get your work done, you should be fine. Just be on the lookout for performance slides from your department. If you overhear talk of your boss being replaced, be prepared to start looking for work yourself should things get really bad. In all reality, many bums don’t get axed at all but go to work and collect a big paycheck for doing virtually nothing! Welcome to America.

5. The Human Pep Talk

Description: This boss is like your typical high school marketing teacher who also doubles as the football coach. Every day he constantly reminds the team of it’s goals and how great it would be if the department reached them. He overuses tired sports lines like, “let’s get with the game plan,” and “We are all going to bat a thousand today, team!” Any baseball fan knows that this is impossible, as are this maniac’s goals. He usually dresses well and is a nearly constant ray of fluorescent sunshine, even on the coldest, dankest of Monday mornings. He’ll make you want to hang yourself with a homemade paper clip noose.

Pros: None

Cons: His constant energy will wear down almost everybody over a long period of time. Even though it may increase superficial morale for your office, it will bring everyone to the perilous edge between extreme productivity and insanity. Nobody likes a football coach as a boss, even if they love the NFL. And they certainly don’t need to be reminded of the scores every single day, both on and off the field.

How to deal with a Human Pep Talk: Transfer offices to a different department or quit entirely. You will burn out, I promise you. Maybe not today, and maybe not even this week, but eventually you’ll go crazy and end up babbling like a child in the corner at Starbucks with a gallon of fresh coffee at your side. Another victim of the “Go team, go” mentality in the sales department.



  • Scott Jackson November 15, 2007 at 4:33 pm

    My boss is some odd combo of 1-3. He likes to micromanage, but not with stuff I’m involved in usually. He’s also very grumpy a lot. I just try to avoid him as much as possible, as does everyone else.


  • Mike November 15, 2007 at 5:03 pm

    There is probably some kind of personality testing system I could come up with that helps fit a boss into one of these categories. I think I’ll work on it.

    At my old job, my first boss fit the avoider description well, while I had a micromanager for my second boss who sometimes become a drill sergeant. Good times!


  • Beth November 16, 2010 at 9:36 am

    I have bosses (plural) who fit a combination of these traits. One is a combo of the Bum and Drill Sergeant, if you can believe it. She does little work herself and can’t be bothered, always out to three hour lunches or hair appointments, but is quick to remind you when you didn’t do something the way she would have liked, even if it was done correctly and efficiently. She’s impossible to deal with and quite an unpleasant person.

    Then there’s my other boss, a combo of Micromanager and Human Pep talk. Quite possibly the worst combo imaginable. She even instigated “staff huddles” on Monday mornings. 🙂 You know, like sales people sometimes have. Except we’re just office minions. They’re just conference calls, thank God; not the huggy smiley puke-inducing hand-holding the phrase brings to mind. I can’t imagine a more productive use of my time than spending the first half-hour of my Monday on the phone not listening to my co-workers because whatever their work entails doesn’t affect me, and then having to make up a list of things of my own to tell them while they’re not listening to me. My favorite thing about her is that once she has instigated a new policy, which is about twice weekly at this point, and always counterproductive in some way to someone, she phrases it this way: “You all need to be doing X and Y and it needs to be done by Friday. I need it done exactly this way, and you need to report back to me by Wed. on your progress. Are we all OK with that?” Haaaahahahaha. Are we all OK with that? Nice touch.

    I honestly felt like less of a child in high school.


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