50 Bad Bosses You’d Never Want to Work For

We asked Rainn Wilson from The Office to help judge your worst boss stories. Whether you laugh in recognition or cringe in outrage, you'll just be glad it's not you.

Photographs by Peter Yang from Reader's Digest Magazine | March 2013

My boss likes to save pennies.

How much? I caught him in the break room retrieving paper cups from the trash can and shoving them back into the dispenser next to the watercooler. He didn’t even bother wiping off the lipstick.—Barbara B., Maryland

After I’d been working in a small marketing agency for two years, my boss called me into his office.

He told me I was finally receiving a promotion and a raise. I was elated. But when I reminded him about it the next day, he reneged. I started to argue, but he cut me off. “You know better than to take me seriously in the afternoons,” he said. “I’m drunk every afternoon.”—Elizabeth B., Georgia

While on the job, I was unpleasantly surprised by the early arrival of my monthly cycle.

After unsuccessfully begging every woman I could for “logistical support,” I reluctantly approached my supervisor, Jerry, and, choosing my words carefully, stammered, “I…um…would like to request permission to go home. I am…having trouble with…a female issue that…I’m not able to successfully resolve.” Poor old Jerry said, “Sure, no problem. But tell me, which female?”—Glenda Herrin, El Paso, Texas

It was a typical hectic Friday afternoon at our law office.

My boss, meanwhile, was hundreds of miles away at a luxury resort preparing for a meeting. In the midst of my insane day, I got an urgent call from him. “You have to phone the hotel right away. It’s important,” my boss said. “Ask them to send someone to the pool area immediately.” “What’s wrong?” I asked. “We haven’t seen a waiter in 20 minutes, and we need our drinks refreshed.”—Bonah Bachenheimer, Long Beach, California

Once after work, my boss, a self-titled “e-mail man,” sent me a text message instructing me to check my e-mail.

I rushed over to my computer and pulled up the important missive. It contained two words: “Call me.”—Martin Hoffmann, Pearland, Texas

My boss was notoriously cheap, so when he handed me a birthday card, I was pleasantly surprised.

“Thank you,” I said. “You’re welcome,” he replied. “And when you get through reading it, take it to Robin down the hall. It’s her birthday today too.”—Gail Snyder, Georgia

Our former department head was famous for his malaprops.

Here are his greatest hits:

• The Greek pyramids weren’t built in a day.
• Spurt me out an e-mail.
• Let’s not put the horse before the cart.
• Tonight we’re eating at the Tibetian restaurant.
• It’s not rocket surgery.
• It’s all smoke and windows.
• Nothing is nailed in stone.
• Sometimes you have to roll the dice, and it comes up tails.
Steve Wehmoff, New York

I was five and a half months pregnant, and the principal decided it was time we had a chat about dress code.

My dress code. “I don’t know if you are aware, but your body is changing,” she said awkwardly. “I’m concerned because your breasts have become inappropriately large for a secondary school teacher.” Long, uncomfortable pause. “That’s all,” she said, dismissing me. She never did say what she expected me to do about the problem.—Kristen J., Tennessee

I stayed late with my boss fielding customer queries.

But after one call, a look of horror crossed his face. “I have to get out of here!” he yelled. “That was my girlfriend. Her husband is in a motorcycle gang, and he just found out about me. He’s on his way over here right now!” The husband had never laid eyes on him, he said, but knew he worked late nights at the newspaper. My boss then left me with these words: “Keep answering phone calls from customers!” And out the door he went. Being eager to please, I stayed put. But then it hit me: My boss was setting me up. He was hoping I’d be mistaken for the boyfriend! I quickly grabbed my coat, turned out the lights, and got out of there.—Phil P., Pennsylvania

At my old office, one of the bosses went crazy and threw his computer out the window, 50 floors above street level.

It bounced on a ledge a few stories down and stayed there, thankfully. Later, he was taken out of the office in a straitjacket. Oddly, he returned to work a month later.—B. O., Montclair, New Jersey

Shortly after 9/11, our division manager wanted to do something to unite the company.

He told my boss to assemble everyone in the boardroom and to place the lyrics of the national anthem on each seat. On the day of the event, I had filled the room with streamers, balloons, and small flags and, as requested, had placed a song sheet with the lyrics of the national anthem on each chair. “What’s this?!” the division manager shouted at me. Pointing to the song sheet with the title “Star-Spangled Banner” on it, he continued, “I wanted the lyrics to the national anthem!”—Anonymous

My boss’s assistant, an efficient middle-aged woman, spent much of the morning transcribing a letter he had dictated.

She suddenly let go with a string of expletives, words I’d never realized were in her vocabulary. “Is everything all right?” I asked. Steaming, she rewound her digital dictation device a few seconds and let me listen to what she had heard: my boss saying, “No, no, forget all of that. [Pause] ‘Dear sir …’”—Johnny Walker, Kempton, Pennsylvania

I was working as a reporter for an “alternative” New York City newspaper.

Our office was a storefront with a double door. The publisher owned a small Honda, a tiny 1970s model no bigger than a shopping cart. Or so it seemed, until he decided to park it in the office at night to avoid the hassle of parking on the street. “It will never fit,” we told him. “Sure it will,” he said. So we pushed all the desks against the wall, and he backed the vehicle across the sidewalk. Sure enough, the rear end of the car made it through the door with an inch to spare on either side. Wow! This was actually going to work! We were going to park a car in the middle of our office! Alas, no. Half an hour later, and dizzy from breathing carbon monoxide, he could not squeeze the side mirrors through the doors. The strange thing is, as we moved our desks back, I was as disappointed as my boss that his scheme didn’t work.—D. N., Morristown, New Jersey

After I worked through lunch to help my boss with a report, he offered to show his appreciation by taking me out for a bite.

The place he had in mind had a wonderful buffet, he said, with foods from around the world. I was absolutely salivating with each detail. So what was his idea of an exotic dining establishment? Sam’s Club. We spent the hour dining on the free samples they handed out.—Wendy Brown, Illinois

I’d gone on vacation without having processed a pay raise for one of the employees of our medical practice.

When I returned, I discovered that my boss had filed the forms away. I opened the file cabinet and looked up the employee’s last name, first name, subject matter—nothing. “Hey, where did you file those papers?” I asked my boss. “Look under M,” he said. “M?” I asked. “But his initials are C. S. Why would you file it under M?” Exasperated, he said, “For money.”—Deborah Bush, Virginia

My boss’s biggest nemesis is the English language.

During one meeting, I asked about the status of a particular report. He replied, “We aren’t going to prepare that report. It would be an exercise in fertility.” It would be funnier if he didn’t earn four times more than I do.—Sue T., Ohio

The front office asked us to figure out the square footage dedicated to each department in our clothing store.

To save time, I suggested we count the ceiling tiles above each department. “They’re each two square feet. Counting the tiles would give us an accurate dimension of each department without having to work around all the displays,” I explained. My boss hated the idea. “He-lloo,” she said, sarcastically, “we need the square footage of the floor, not the ceiling.”—Terri Hanke, Kansas

As a teenager, I worked at a diner that had an all-glass front.

One day, a blizzard blew in, knocking the wind chill factor down to 40 below. But my boss sent me outside anyway to wash the windows. “Put some alcohol in that bucket so the water doesn’t freeze,” he said. “The water? What about me?” I asked. He grunted, “You’re too young for alcohol.”—Scott Donovan, Charlton, Massachusetts

On my first day at a new job, I arrived to find someone in the office that I’d been told would be mine.

Puzzled, I went to find the person who had hired me, but she was away at a conference. So I told another person my story. She made a few calls, then told me to find a place to sit. “Don’t speak to anyone,” she ordered me. “Just wait for someone to find you something to do until your boss returns.” Turns out, before my boss left town, she had forgotten to fire the person I was replacing.—Nancy E., Massachusetts

My boss was a real gentleman.

Although it wasn’t my job, he once made me mow the lawn around our office building. I was wearing a dress and high heels.—Tamara T., Nebraska

During a faculty meeting at our school, our principal grew frustrated with the lack of attention he felt was his due.

Raising his voice, he shouted, “Listen, people. Communication is a two-way street. When I talk, you have to listen.”—T. D., via Internet

My (former) boss had a surprise for me one day.

“I brought in muffins,” he said. “They’re in the break room. Help yourself.” Of course, I ran to get my fill. But when I got there, I found all the muffins were topless—only the stumps were left. “What gives?” I asked him. “Oh, yeah,” he said. “I only like the muffin tops.”—Carl Graf, Tewksbury, Massachusetts

As an employee representative, it was my unfortunate duty to do battle with our boss whenever he asked too much of his employees.

“You think you know everything, don’t you?” he yelled at me once. “No, sir, I don’t,” I countered. “But I do know what the law says. And the law says—” “The law!?” he roared. “The law has absolutely nothing to do with what goes on in this company!”—Y. F., Bellevue, Washington

I was performing with another comic, and part of our deal was a free meal.

After my set, I asked our waitress if I could get a bite. She said no, so I asked to speak with the manager. Next thing I knew, he was charging straight at me, screaming that I was rude to his waitress. He chased me around the table, yelling and lunging at me. Thankfully, the bouncer separated us. When the other comic got offstage, I said, “You won’t believe this, but the manager tried to kill me!” “Really?” he said. “I didn’t think your set was that bad.”—D. F. Sweedler, New York, New York

During my brother-in-law’s first performance review, his boss said, “I’m not quite sure what it is you do here. But, whatever it is, could you do it faster?”

Jeanie Waara, Philip, South Dakota

If Workers Could Talk Back

Fark.com asked readers, “If you could say anything to your boss—anything at all without repercussions—what would you say?”

• “Your yellow shirt and red tie make you look like Ronald McDonald, sir.”
• “Would it be too much to ask for you to actually read the summaries instead of making us summarize the summaries every day?”
• “Quit dressing like Snookie from Jersey Shore and dress for business.”
• “We all know it’s not iced tea.”
• “No. Why don’t you get in the Chuck E. suit.”
• “Do you know why you don’t think Dilbert is funny?!?”
• “You remember that one time we were at this bar and you chugged a whole pitcher of beer? That was awesome.”


Five recent, true stories about getting fired:

• A New Zealand office worker was axed for using bold, uppercase letters in an e-mail to coworkers on how to properly fill out forms. The company deemed the capital letters confrontational.

• Wells Fargo fired a customer-service representative with seven years on the job after discovering he’d put a cardboard cutout of a dime in a Laundromat washing machine nearly 50 years earlier.

• A waiter in Fort Lauderdale, Florida, claims he was let go after leaving his post to help a woman who was being carjacked in the parking lot.

• A fashion model was reportedly fired for being too fat. The model is five ten and weighs 120 pounds.

• A Chicago car salesman was shown the door for wearing a Green Bay Packers tie to work.

Sources: New Zealand Herald, Associated Press, wsvn.com (Fort Lauderdale, Florida), stylelist.com, espn.go.com

My boss...

... was divorced
I was fired by my boss because of the way I laugh. Apparently, it reminds him too much of his ex-wife’s laugh. I’m a guy. (fmylife.com)

... is empathetic
My boss hired a guy who was color-blind to do color corrections at the photo lab. After angry customers returned their pictures, I informed my boss. She told me that I was putting him down to build myself up. (jobs.aol.com)

... is a menace
Last night, my boss dropped his cell phone in his pool, so he put it in the dryer. Now he’s out a phone, and his dryer needs servicing to remove the tiny shards of glass caused by the phone screen smashing apart. (mystupidboss.net)

My boss...

... is a lover of the arts
My boss overheard me tell coworkers that I’d gotten tickets to a concert. Later, he said I had to work the night of the show. He then offered to buy the tickets from me for half of what I’d paid for them. (fmylife.com)

... loves to entertain
My fiancé and I were invited to a party that my boss was throwing. She said how pretty my white blouse and black skirt looked on me and suggested I wear it. When we arrived, she introduced me to the caterer as the waitress and showed my fiancé to the bar where he would be working. (jobs.aol.com) ... is a teetotaler
Our bar owner told us to begin cutting off drunk patrons. Pointing at me, he said, “When they start hitting on her, they’re too drunk to drive.” (fmylife.com)

My boss...

... is otherworldly
Our chief executive made decisions based on graphology and astrology. She would secretly acquire handwriting samples from new staff and decide on appropriate placement for each person based on the results. (bobsutton.typepad.com)

... is xenophobic
My boss told his wife that the Great Lakes are a man-made border to separate us from the Canadians. (mystupidboss.net)

... is not a cook
My editor left a note on a recipe story I was working on. It read “Please be specific. Do you have to peel the egg before you boil it?” (forbes.com)

My boss...

... is a quick study
You would be talking with my boss, and suddenly she would snap. She’d lock eyes with you, and her voice would drop very low. It turns out that she learned this technique in obedience class with her dog, and she found it to be an effective “tool” in managing people. (jobs.aol.com)

... is short
I was chewed out by my boss because, according to him, I look down on him. I’m six five. (fmylife.com)

... is a delegator
My supervisor’s 80-year-old mother-in-law was in his office upstairs from mine. He called my name, and I ran upstairs. He was on the phone. Without hanging up, he said to me, “Would you mind giving her the Heimlich maneuver? She can’t breathe.” (jobs.aol.com)

... is a narcissist
My boss gave the first employee-of-the-month award to himself. (bobsutton.typepad.com)

Become more interesting every week!

Get our Read Up newsletter

Sending Message
how we use your e-mail

Your Comments

blog comments powered by Disqus