Top 40 Bonehead Boss Stories

Three things are certain in life: death, taxes, and bad management. With that in mind, here is a collection of horror stories about real-life bosses in real-life situations. Like my recent post "The 32 Dumbest Things that Real-Life Bosses Said", this post is based on material that my pal Larry Jacobs and I compiled for our talk radio program, Funny Business, which used to run on WRKO, the big talk radio station in Boston.

Some of these stories may have already appeared on the Web, but this is first time they've been gathered into a comprehensive list. Readers welcome to add their own stories as comments, of course!

#1: I worked as a secretary for a large metropolitan hospital. My son was in day care at a local church. One day a co-worker ran into the office and screamed "the church is on fire, the church is on fire". Immediately, I ran to the church, where I could see the smoke, the fire, four fire engines and people everywhere. I was in a panic. I lost my shoe, tore my dress and dropped my purse looking for my son. After finding him (Thank God!), I returned to work frazzled and disheveled. When I made it back to my desk, my Boss approached me and said "You left your station without permission. You will be disciplined for this!"
#2: My company has certain key programs, part of what they call their "strategic vision." All other projects are considered "non-strategic" and get no funds for capital equipment, research or marketing. After my non-strategic department's sales beat the rest of the company for three straight years, they renamed my department "Strategic Systems."
#3: I work in the library of a major college. The Director instituted a computerized card catalog and checkout system which required each book, all 100,000 of them, to be barcoded. She wanted this done quickly and told everyone that we would be working a full day on Saturday. We all showed up and worked 9 hours. On Monday we learned there would be no overtime pay for Saturday. When approached, the Director said "Oh, Saturday, that was volunteer work".
#4: After months of hard work, I closed a deal for $7,000,000. My customer bought the equipment because of our strong personal relationship and my company's technical capabilities. Six months later they doubled the order. My Bosses, thinking that they had closed the deal, limited my commission to a fraction of what it should have been. I found a new job and quit. A week later my customer moved the order to my new company.
#5: 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: I work part time in a lumberyard which had theft losses. Aha! said management, it must be our thieving employees. Polygraph tests were ordered for every employee. I flatly refused to take the test. Since I was the leading sales person, I was threatened, but not fired. A week later, during a routine, late night drive by the police caught the thief loading a truck with material from the yard. It was the VP who had ordered the lie detector tests.
#7: I had a job working at a summer camp during college. I had worked at this camp for five summers. This particular summer my best friend unexpectedly died from heart failure and I took leave to go to the funeral. When I returned, my grandfather was on his deathbed and my mother asked me to request more time off. Obviously upset, I approached my Boss and explained the situation. She said "Well, you're just going to have to get over it and get on with your life. I can't let you go again." My grandfather died the next week. When I told my Boss she said "You should have planned better, you have no bereavement time left."
#8: Recently, the plant were 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.
#9: At the publishing company I work for, management regularly stressed their policy of promoting from within. When a middle-management opening occurred, the divisional vice president told my Boss about the opening. He said "Even though there's an opening, don't post it in your department. Someone unqualified might apply."
#10: Last week my Boss discovered the motivational quote "Only in the dictionary does SUCCESS come before WORK". He ordered a large banner for our work area with an "improved" version of the quote. The banner reads: "Only in the dictionary does SUCCESS come before HARD WORK".

#11: In a group review meeting, my Boss turned to one of his direct reports and said "I'm told a strong manager will admit to his mistakes. So tell us, how did YOU manage to lose so much money?
#12: A vendor's rep held a meeting with the executive staff at my company. After a frustrating afternoon in which the only opinions expressed were those of the owner of the company, the exasperated rep exclaimed, "Are you all just a bunch of 'Yes' men?". To which my boss replied, "Of course not! If the owner wants us to say 'No' we're 'No' men!"
#13: After asking each manager to spend two weeks preparing detailed building and capital improvement "wish lists" to plan our facility's budget, our supervisor said "Oh...your wish lists are just that...don't expect anything you requested to actually get done. It was just an exercise!"
#14: I recently wrote a justification to buy a new computer. It had to be approved by my boss. Unhappy with my writing style, my boss re-wrote the justification to show me how it should be done. After it was finally written properly, he turned it down.
#15: 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."
#16: One day I was called into my boss' office and asked to take the lead on a benchmark project. Over the next seven month period, I traveled and worked 16 hours per day, seven days a week. My team accomplished the impossible. Two weeks later, my Boss announced major layoffs. He saved two people in the department, but I wasn't one of them. After such stellar performance I had to know why I was let go. He said "Your last project was good. It just didn't give you the right management exposure to save your job."
#17: I was working with my Boss to prepare for a big meeting with the executive vice president of our division. My wife and I were expecting our second child at the time. Ahead of schedule, my son was born a month premature, the weekend before the big meeting. On Monday I came to work to tie up a few loose items, and to tell my Boss about my son and his critical life situation. Looking up from his slide rack my Boss said "Don't let you personal life interfere with your job. It can only hurt you, professionally"
#18: 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.
#19: After two and one-half years of college I quit and got a job at a major retailer. I quickly learned the ropes and, within the span of eight months, began training the newly hired managers on how to do their job, as well as mine. I repeatedly asked to enter the management training program, seeing as how I already knew how to run the store and had already proven myself as an outstanding employee. My district manager repeatedly denied my requests, while hiring management trainees with no retail experience or degrees in related subjects. I finally confronted my Boss when a fellow associate was promoted after being with the company for three weeks. She said "It takes experience and education to get ahead. You'll need a college degree to be successful, here."
#20: 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."

#21: 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.
#22: My Boss heard there was an opening for a plant manager in our South American facility. To better prepare himself he decided to attend Spanish classes on the company's time and at their expense. The only problem? The plant is in Brazil where they speak Portugese!
#23: I work for a big management consultancy partnership. We pride ourselves in the quality of our internal education programs. However, once it consumed too much non-profitable time one of the senior managers suggested we make the "Team Building Exercise" into an "individual self-help study course".
#24: I was hired as a third shift security officer in a local chemical plant. The company was losing supplies and they wanted me to investigate. After just two weeks, I informed the Plant Manager that the foreman on third shift was carrying the goods off the rear docks. He said "My Brother?"
#25: 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?
#26: On Monday, my Boss approached me at 4:00 PM with an emergency assignment. He had an important meeting early the following morning and needed a new version of a 400-page document. I worked the all-nighter, made the updates, and left the manual on his desk. I left to go home at 7AM the next morning. When I came to work that Wednesday, I asked his secretary about the important, emergency, client meeting. She said "Oh, he decided to cancel. He took a few vacation days instead."
#27: A new computer department director had been hired. Everything was normal for several months. Then, as usually happened about once a year, a reorganization was announced. The entire programming department of about 60 people was crowded into a small room, with half of the people standing. An organization chart was projected on the wall in small print. I squinted to find where I was assigned. The guy next to me said, 'I don't have my glasses. Where am I?' I couldn't see him either. Then the director said 'If you don't see your name on the chart, see me after the meeting".
#28: Concerned about low company morale, our COO purchased a series of "motivational posters," -- brightly-colored inspirational scenes bedecked with doggerel about teamwork. These posters hang in the hall next to the time clock...right by the memo explaining the company will no longer compensate workers for time not registering on the clock, regardless of whether the error is human or mechanical.
#29: 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.
#30: 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!!"

#31: 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."
#32: The Human Resources Department in my agency recently sent out an E-mail message explaining a change in retirement procedures. Subject of the message was "Simplified General Rule". The message was two pages long, contained six paragraphs, a calculation formula, and two tables. One week later, a one-half page message with the same subject was sent out clarifying the first.
#33: My company recently showed a video during one of our monthly review meetings. The video talked about the importance of working together in a morally and ethically pure state. It expounded such virtues as optimism, hard work and honesty. It claimed that an honest management would cultivate honest employees. The movie was very uplifting and motivating. Just before the lights came on, the last message ran across the screen. It read "FOR DEMO PURPOSES ONLY -- ILLEGAL TO USE FOR TRAINING".
#34: A few years ago the President of our company concluded one of the quarterly all-employee meetings by asking, as he always did, if there were any questions. No one asked any questions. He then said, "I keep holding these meetings, and no one asks any questions. I would like someone to ask a question." One brave soul raised his hand and asked a question. The President then said, "Well, if you had been listening to what I just said, you would know the answer to your question. Any more questions?"
#35: My wife went into labor with our first child on New Year's Eve. I called and was granted an emergency day off. After intense labor my wife had a C-section and therefore needed at least one week of bed rest. Like a proud father, I went to work the next day, to advise my Boss on the birth and my son and my need for five more 'emergency' days. Without any congratulations, my Boss said "Sorry, you can have three days, but not three consecutive days. We need you here, too."
#36: I was finishing a spreadsheet my Boss had created. Shortly after I started, I noticed that the numeric entries were freely intermixed, some were numbers, others were text. One value would read "1005.29" and the next would read "one million". I alerted my Boss to the problem. First he laughed at me. Then, as if explaining something to the village idiot, he said, "Let me show you how we compute the totals. " He pulled a calculator from his pocket, and one-by-one, he computed the total. When he was done and his chest was full of pride, he said "Now, just type this number in at the bottom."
#37: 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.
#38: I was refused a raise by my VP. He said, "You're already making more money than I was at your age." I was 24. He was 46. It turns out that he spent his 20's touring around the state playing guitar in a garage band, barely making enough to pay for food and gasoline. When I pointed out that rather than playing guitar, I had spent my youth getting a college degree and working in a high-tech job, he replied, "What's your point?"
#39: 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."
#40: Our purchasing group was negotiating with a major paint supplier. Because of our volume of orders, we were in a strong position to negotiate. Finally, after two days of heated wrangling, we got the manufacturer to agree to a 35% discount. As we were about to sign the contract, the President, who had not been a party to the negotiations, walked in and tore it up. He said "I'm going to teach you purchasing people how to play hardball. That's the way you make it in this world." At that, he turned to the manufacturer's representatives and said "We'll give you 10% under your quoted price, take it or leave it. There are other suppliers out there." The supplier quickly leaped at the change. Turning to us as he left, the President said "I hope you learned something from that."

READERS: Feel free to share your own tales of management boneheadery!

NOTE: Interested in a sales career? My new book How to Say It: Business to Business Selling provides easy step-by-step tutorials for novices and experts alike. It's now available for purchase at:

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