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Bad Boss Stories That’ll Make You Laugh or Cringe

Life pretty much guarantees that you’ll get a bad boss at one point or another. Sometimes I think that there are as many bad bosses as there are ants in the world; however, at least you can recognize the good bosses after experiencing the rotten ones that make you want to look into entrepreneurship.

The Boss What Set Me Up

“I once had a boss who knew that I needed to go to physical therapy sessions due to an accident. He told me that wouldn’t be a problem. Yet, when one of those sessions was at the end of the day on Friday—he had plans too. So in front of a very senior leader at the company and a client, he said that I’d take the lead on it, then took off.”

The boss Who Didn’t Let Me Use the Bathroom

“My first job out of college was in sales, but it operated much more like a call center (mistake number one). As a result of the high volume of incoming calls, every rep was required to be on the phone and at their desk at all times. That meant we had a ‘bathroom request’ button on our computers. Any time you had to use the restroom you’d click the button, cross your fingers (or legs!), and hope for the best. The requests got kicked up to my not-so-great manager and nine times out of 10 denied immediately.”

The Boss Who Made Fun of Me

“My doctor advised me to lose a few pounds and get more exercise. After I mentioned this to my Boss, he emailed me a ‘motivational’ image of a Baywatch babe with my face and hair. A month later I gave notice. This time, he emailed me an image of a pig with my face on it.”

The Boss Who Wanted Me to Steal

“I worked for the federal government. My boss wanted me to assist him with stealing a $2,800 laptop for his daughter to take to college so he could save some money (he was paid about $168k a year). I refused and he fired me. I filed a complaint which was promptly ignored by his superiors. I lost a $100k-a-year job because of this sociopath. What makes it worse is that he was shortly thereafter caught stealing from the government, but was not fired because he had been there for more than 25 years and his boss ‘did not want to ruin his career.’”

The Boss Who Called Me “Intern”

“When I was an intern at a PR firm, my manager would make me run her personal errands (pick up dry cleaning, ship things, drive her and her friends to SXSW events, etc.). She would get my attention by calling me ‘Intern.’ At more than one off-site team building event where alcohol was served, she not only pressured me to drink and made fun of me when I didn’t give in, but she also told me, at length, about her recent sexual exploits with a married real estate agent. Needless to say, when they asked me to stay on full-time, I politely declined.”

The Boss Who Wanted to Fire Someone

“I once had a boss who decided that, despite very strong performance, they didn’t like someone on our team and wanted to see them gone. They didn’t have the ability to fire them, but looped the employee out of emails and conversations, talked poorly about them behind their back, and disregarded any good performance. Not only is that unethical (and possibly illegal), but it also made actually getting our team’s work done way, way harder.”

The Boss Who Embarrassed Me

“I once had a boss who, while I was replying to a question addressed to me by their boss in a meeting (with whom I had worked before and had developed rapport), actually put their hand less than an inch in front of my face to silence me so that they could answer instead.”

The Boss Who Was Greedy

“I worked on a HUGE project for an engineering firm. EVERYONE was FORCED to work long overtime hours to finish it on time. A large portion of this overtime work went unpaid. Management frequently threatened the workers since the employment market was tight. When the project was finally completed, the staff was called together and berated terribly. My Boss was particularly upset that this project was late. Later that day I talked to one of the clients on the phone. He seemed to be very happy with our work. Towards the end of our conversation he said ‘Well how did yawl split up that $300,000 bonus we gave you for FINISHING AHEAD OF SCHEDULE?'”

The Boss Who Didn’t Value My Time

“I once had a boss who nearly always multi-tasked in meetings by being on her phone and present in the meeting. In both 1:1’s and in group settings she would shift her attention constantly from the speaker to her phone—back and forth, back and forth like this for the entire time. At first, I just thought she was extremely busy, and it was the only way for her to get everything done—until one day, I caught her doing crossword puzzles on her phone while doing a check-in with me.”

The Boss Who Gave Conflicting Information

“I work for a large communications firm. After some ‘down-sizing’ in our department a group of us went to the VP and asked about our job security. He replied ‘You are 100% secure.’ Two days later, we got pink slips for a month-end layoff!! The following week the President came to speak to us. He said, ‘I know you have gotten conflicting information in the past, but yours will be the last layoff for now!!! That should make you feel better.'”

The Boss Who Showed Too Much Appreciation

“My last promotion entitled me to two new departmental benefits: a chair with arms and a bigger cubicle. Since I didn’t see the need to disrupt my life and move another employee for 4 MORE INCHES, I declined the larger space. I was very comfortable where I was. But my Boss wouldn’t let it die. He got maintenance workers to ‘reconstruct’ my area. It took them all day to add an 18″ panel to my cubicle. When the work was done, my Boss stopped by. With a big grin on his face he said ‘Now this is more befitting of your new status.'”

6 Management Solutions to Increase Employee Productivity

The Boss Who Micromanaged Me From Home

“Although I’d gotten approval to work from home one day a week (my boss WFH three days a week!), if I took my eyes off of my computer screen (we used Gchat to communicate throughout the day) for three minutes, my manager harangued me. She told me I’d lose my remote privileges unless I started letting her know when I was getting up to take the dog outside, make a cup of tea—or use the bathroom.”

The Boss Who Spied

“Recently, the plant where I worked was faced with a union drive. In order to determine who was ‘at fault’ the President arranged for private meetings so they could air their issues, with no supervisory or managerial personnel were allowed in order to ensure that all comments would remain confidential. During the meetings, I happened to visit the HR manager’s office and surprised him by just walking in. After I was seated he indicated that I should be quiet and then he readjusted the intercom. He was listening in on the ‘private’ meetings. The President had ‘bugged’ the room and the HR manager was furiously taking notes, so that the President could ‘get even; with the workers.'”

The Boss Who Offered Too Much

“When I was hired, my boss promised that I would be making a very handsome salary by the new year. Although the starting salary was less than I wanted, I took the job based on his promise. Over the next few months it became apparent that his promise might not be kept. When I confronted him, he said ‘I tried to get that raise for you, but the front office won’t allow it.’

‘Why, then, did you quote me a figure that you weren’t authorized to give?’ I asked.

He said, ‘When I made you the offer, I quoted you the salary that I WISHED you could get.'”

The Boss Who Ditched Me

“I am the manager of the secretarial pool. One night a manager came to my office in a panic. He said he had a very important proposal that HAD to go out that night. It was 5:00 o’clock, I was tired and I refused. Before I could leave the department the sales rep managed to reach the VP who called and ‘convinced’ me to get it done. Before I started the proposal, I told the manager that I would miss my ride and as a result, I would be without a way to get home. The manager offered to take me home and said he would be waiting in his office upstairs. Without that worry I went to work. I worked non-stop until 8:00 p.m. Proud of my accomplishment, I carried it up to the salesman’s office. The floor was empty and his office was dark. The cleaning crew said he left at 5:30.”

The Boss Who Wanted to Pay Me Less

“Our company was running into financial difficulties and my Boss asked me to work for half of my salary. I said, ‘Well, I can work half the time for half the pay.’

He said, ‘Oh no. What I mean is… you usually work 80 hours a week with 40 hours of unpaid overtime… now I want to pay for just half of the first 40.'”

The Boss Who Robbed Me

“I work for a family-owned check cashing company. Yesterday, I was robbed at gun point by three bandits. Today, the owners want to deduct the stolen cash from my pay check. They say I willingly complied with the bandits’ wishes.”

The Boss Who Tried to Fire Me After I Quit

When I resigned, my Boss asked for more than the normal two week period. He wanted as much time as possible to find a replacement. Since my new job didn’t start for six weeks, I found it easy to comply with his wishes. After three weeks I told my Boss I could no longer work weekends because I was moving out-of-state. However, sure enough, despite my requested restrictions, I was scheduled to work all seven days in my final week of work.

‘I can’t work Saturday and Sunday.’ I told my Boss.

‘You’ve had the last two weekends off.’ he replied, ‘You have to work or I will fire you.’

‘I’ve already quit.’ I told him. ‘I am working this week as a favor to you.’

‘You’re FIRED!’ he shrieked.

‘Fine.’ I shrugged and started out the door.

Before I could reach the door my Boss caught me. He said ‘What are you doing? You can’t leave yet! You’re not fired until the end of your shift!!'”

The Boss Who Could See the Future

“After I got engaged, I went to my Boss to schedule time off for the wedding and honeymoon, which was still more than a year away.

My Boss said, ‘I don’t know if that’s a good time. We’ll just have to wait and see.’

The Boss Who Took My Trophy

“I’m a web page designer for a university. I was called by a prominent organization that we belong to and told that I had won first place for a design. The prize was going to be given to me at a banquet in California. Immediately, I told my boss that I wanted to go and accept the award. Without offering congratulations, he said that the budget was tight and that the university couldn’t afford to send me. The following week my boss went to accept the award for me. After seeing the award, he discovered that my name was engraved on it. He made the committee re-issue the plaque, blank. Now, my award hangs in his office.”


Asian girl emoji holding her hand outReferences:

The Worst Boss I Ever Had: 11 True Stories That’ll Make You Cringe

5 Bad Boss Stories That Will Make You Grateful for Your So-So Manager

Top 40 Bonehead Boss Stories

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About the Author:

Sophia Tinsley is XTech Staffing’s Marketing Specialist and writes career-advice related articles and content for the website. She also manages XTech’s social media platforms. Sophia recently graduated from Texas State University where she earned her BBA with a major in Marketing. She is the crazy cat lady of the office and the embodiment of Michael Scott – she always has wacky ideas. Sophia also writes for her personal fashion blog and creates movie trailers as hobbies. She thinks she’s unique, but likes all things “basic” (i.e. Starbucks). And if you’re a Game of Thrones fan, then you and Sophia will get along swimmingly.
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