Maybe an employer asked you a ridiculous question, or maybe they demanded you to complete a task outside of your job scope. Without thinking, you spout off a sarcastic response. Hey, no worries! We’ve all been there. In fact, it happens more often than you would think! These employees share the most insane, rude, or downright questionable things they’ve said to their bosses. We recommend you don’t try these at your job! Content has been edited for clarity.
Tech Company Triumph Part One
“I worked for a high-tech company when technology was just starting to make an impact on the world. This was before the internet, even before everyone had PCs. We had one PC for our entire department at work, and it was a thrill to use it.
The company I worked for made high-speed modems, but since the technology was new and difficult to produce, they were ten thousand bucks a piece. Plus, you needed at least two modems for them to work properly. The modems worked at lightning speed at the time, and the benefits were immediately apparent. Every major company wanted them and didn’t care about the cost. Unfortunately, the techniques we were using were in their infancy and had lots of bugs. Even though we were selling them like ice cream on a hot day, they didn’t work as advertised.
A huge oil company bought a massive amount of products from the company I worked for. They planned to link all of their gas stations across the United States to their central site and have the managers report daily sales to the home office. This previously had been done by mail or phone, but it was a slow and inefficient process. With a modem system, they could know what their revenues were to the penny overnight, or even several times during the day. They did some cursory testing on the devices and rolled them out. However, they didn’t work.
Our engineers worked day and night to fix the issues, but they turned out to be intractable. There were grave concerns about how we might never solve the problem. Our salesman for the company was a brave and confident expert with years of experience, but even he was becoming increasingly despondent. The customer was agitated, angry, and threatened to return the product. This would have been a huge setback, possibly a terrible blow to the company. They were by far our most significant customer and by far the most profitable sale we had ever achieved. And the salesman would not get his commission.
I was the manager of the business unit, newly promoted to the role at the age of twenty-six. I thought I was something special, and to be honest if not modest, I was a worldwide expert on these technologies. But what I didn’t know how behind the scenes, the senior managers of this customer were now demanding a reckoning with our company. Our management knew it was the end if we did not have a solution, and we had no solution.
The salesman set up a meeting with the senior vice leader of the oil company, a man who had an immense amount of power. Suddenly, the leader of our company had a ‘pressing business issue’ in Europe. So did every other executive down the line until, casting about, they looked at me. I was to be the sacrificial lamb they would send to speak to the oil company executives. I was told to go ‘make nice’ with the customer to buy more time. I was unaware of the issues behind the scenes. If I failed, I would be unceremoniously fired as a token of good faith. The salesman knew it, but I did not.
Thinking this was going to be yet another triumphant visit, I went out, bought a new suit and briefcase, and flew from Boston to the West Coast. I didn’t even have anything to put in the briefcase except a pad and pencil since I wasn’t given any progress report, possible solutions, or any token to distract them. My managers were so certain of disaster, they thought it best I go completely in the dark.
I was picked up by our salesman in his new Jaguar, along with our field engineer, both of whom knew the gravity of our situation and how dire things were. I was cheerful and humming in the car as I took in the sights. I was surprised by their gloomy silence until we got to the customer’s campus. I had never seen anything like it before. Oil money could buy anything, and the building was modern and massive. The lobby was quite literally an art museum with original paintings.
As soon as my colleagues and I announced ourselves, we were shown to a conference room. This is when I got scared. The room was huge with an impossibly long conference table surrounded by the most expensive leather chairs money could buy. There were tuxedoed waiters with white gloves bringing crystal glasses for the pitchers of water. There was a stenographer with a real steno machine to take the minutes. The room was already filled with executives and lawyers speaking to each other in low voices and grim expressions. After looking around, I instantly knew I was doomed.”
Tech Company Triumph Part Two
“Finally, the door opened and the senior vice leader walked in. A hush fell over the room. He sat directly opposite me. I blinked stupidly as the sweat rolled down my sides. Next to me, our salesman was gripping his pen like a drowning sailor clutching at a piece of driftwood.
The SVL opened the meeting as if it were a legal proceeding, reading a summary of the problem and all the actions taken to date, emphasizing our failure. As he got into the summary, he became angrier and angrier.
He started pounding the table and he got red as he yelled, ‘Do you understand how much time and money has been wasted on this issue? Your company is made up of a bunch of frauds! I have never seen a product be so misrepresented!’
It was clear all of the SVL’s anger was directed at me.
‘I am insulted your company had the nerve to send you of all people!’ he said while pointing a stern finger at me. ‘If you can’t fix this problem today, right now, around town your name isn’t going to be worth squat!’
And then the SVL sat back in his chair. There wasn’t another sound in the room. Every eye was on me now, and what I would say next. I had nothing. I didn’t even have anything in my briefcase to fumble with for the time being.
And then, without even thinking, I said, ‘Around town, it was well known that when they got home at night their wives would thrash them within inches of their lives.’
I couldn’t believe my ears. To my left, our salesman looked at me in horror and tried to pull himself away from me in his chair. The stenographer looked up from her machine at me. The SVL looked like he was going to begin screaming at me, and I flinched.
Then he stopped.
‘Wait a minute,’ he said, ‘I know the line from somewhere.’
‘Yes,’ I whispered, ‘It’s from Pink Floyd’s ‘The Wall’ album.’
Eyebrow raised, the SVL asked, ‘You like Pink Floyd?’
‘Yes,’ I said, ‘It’s my favorite group.’
‘Mine too,’ he said, suddenly smiling and getting up, ‘I saw them in concert in Los Angeles in the eighties. It was fantastic! I even caught one of Gilmour’s guitar picks. I have it framed in my office with the ticket stubs. Come on, I’ll show you!’
And he got up and walked over to the door. I numbly followed. My ears were ringing and I knew I stunk of sweat and fear. The people in the room were dumbstruck. Everyone had their mouths open or was looking at us in absolute amazement. No one said a word.
As we left the room, the SVL smiled and said to the room, ‘Oh, we’ll give them a few more weeks,’ and he waved them off as we walked down the hall.
The rest of the visit passed in a blur.
The salesman was pounding the wheel and laughing out loud on the trip back to the airport.
‘We gotta get you a great big steak,’ he said, ‘You know, you can only get away with this once in your career.’
When I got back to the office I was the hero of the hour. The salesman had called and relayed the story to everyone he could reach, and I was called into a meeting to recount the adventure. Everyone was laughing and slapping me on the back. It felt good to be the hero for once. Over the next few weeks, we had a dramatic breakthrough in engineering and the problem was solved, the situation resolved, and the customer was saved. The oil company SVL went on to buy many thousands more modems.
Pink Floyd saved the day.”
“Don’t Take This As A Mere Threat”
“I was only fired from a job once. At the time, it was the worst job I have ever had. My father owned a car dealership, and he told me if I ever wanted to work for him, I had to learn the business somewhere else before I could work for him. I had just graduated with an English degree and found a job selling cars.
All car salesmen do not deserve the negative stigma surrounding the occupation, but many do deserve the scorn. Selling cars is a complicated business. Pay is based on sales commissions. If you do not sell a car, you are given a weekly stipend which is deducted from your commission when you finally do sell a car.
My first four months working at the dealership were great. One month, I sold eight cars. The next, I sold twelve. Then, eighteen cars! I was impressed with my natural customer service skills, and I knew my father would be, too.
Then my fifth month at the dealership, I sold twelve cars again. My boss made some comments about me slipping, but I ignored him and stepped up my game. The next month, I sold fourteen cars, but he still commented about my not selling up to the expected standards. There was a board with a list of all the salesmen and the number of cars they had sold in the breakroom. Looking at the list, I was in the middle. I didn’t understand what I was doing wrong.
It was frustrating to have my boss giving me a hard time when it seemed he allowed others to perform at a lower level. When I came close to making a deal, the boss would refuse any negotiation offers from my customers. I was either selling cars at their total price or not at all. He was not helping me sell the car. My next month was the worst ever at the dealership. We were three weeks in and I had sold only five cars.
The third Saturday of the month was a do-or-die day for me to make a sale and salvage my month. As expected, Saturdays are generally the best day for car sales. Even the worst salesman can sell a car on Saturday. This particular Saturday, I planned to sell two or three cars.
After our morning sales meeting, my boss said to me, ‘Can you come by my office? I just need to speak to you in private.’
I followed him in and sat down across from him.
With a serious look, my boss stated, ‘You started strong working here, but your sales have fallen in the past couple of months. I thought you would be better at your job and sell more cars considering your father owns a dealership and you grew up in the business.’
I was speechless, and all I could do was shrug my shoulders.
My boss continued, ‘You need to sell a car by the end of the day or else you are fired. I promise! Don’t take this as a mere threat.’
‘You better hope I sell a car then,’ I replied.
‘Why should I care if you sell a car?’ he asked incredulously. ‘You are the one who will be without a job.’
‘Because if you make me work my whole Saturday and fire me at the end of the day, we are going to fight,’ I said as I made a fist. ‘And don’t take that as a mere threat.’
Shaking, my boss yelled, ‘You’re fired! Get out, now!’
Needless to say, I wasn’t exactly cut out to be a car salesman.”
The Egocentric Business Executive
“Years ago, I was working as an executive assistant, shared between three vice leaders of the company.
One of the leaders was the most demanding and demeaning of individuals I have ever had the misfortune of working for in my life. The other two were quite nice and I enjoyed working for them.
I would typically come in around six or six thirty in the morning to get work done before the day started. Coming into work early was the only time I had to work on my reports or other projects the vice leaders pinned on me.
One day, I got a call from the demanding leader, ‘Mr. M.’ At the time Mr. M called, it was six thirty in the morning, and he was already in a tizzy.
He screamed, ‘Where are the board of directors’ reports? I don’t see them printed and bound sitting in the board meeting room!’
Well, of course, the reports were not printed and bound yet, as he had not asked me to complete those tasks. He did not even tell me about how he was going to a meeting in general.
Mr. M continued, ‘I need thirty copies of the report as soon as possible. And, you need to collate and bind the reports so they look presentable.’
The company had a printing room where I could complete the tasks, but only one printer. The report was over one hundred pages long, and the company printer was painfully slow.
An hour went by, and Mr. M texted me, ‘Where are you? More importantly, where are my reports?’
I rolled my eyes and replied, ‘I am still busy binding the reports, and I am waiting on the printer to finish up.’
All of the sudden, Mr. M blew up.
He texted back, ‘I only wanted pages eleven through thirteen! Are you stupid?’
I sighed and scrapped the jobs on the printer. I printed out the three pages and bound them so they looked professional.
Ten minutes later, I received another text from Mr. M.
He angrily said, ‘Where are you? Do you even know your way around the building?’
I was beyond upset at his tone. I finished up and placed the reports in a box. Then, I calmly went around the office looking for someone, anyone. Finally, I found a director who had come in early.
I handed the director the box and asked, ‘Can you please deliver these to Mr. M?’
The director was confused, but he smiled and asked, ‘Why?’
I smiled slowly and replied, ‘If I see Mr. M, we will have issues. In fact, I will drop everything just to fight him. And trust me, a fight is the last thing he wants. I quit.’
By the time I got home, roses were waiting for me with an apology letter, signed by the other two vice leaders.
One of the vice leaders called me in tears and begged, ‘Please come back! If you do, I promise you will never have to work with Mr. M again!’
I returned, and they moved Mr. M to a different department. It served him right.”
“The Office Was In Something Of An Uproar”
“When I was eighteen, I worked as a network administrator at a nonprofit law firm. There were a pair of creepy toy pigs sitting around the office, and I didn’t care for them. We worked with a lot of minors, so I was sure someone thought the toys put them at ease. However, the toys looked like something out of a horror movie, and even the executive director dreaded them.
One night, upon learning of her fear of them, I picked the lock of her office and left them sitting, in separate chairs, staring at the door. I re-locked the door and went home.
The next day, the office was in something of an uproar.
Lacking common sense at that age even more so than I do now, I copped to it immediately, explaining, ‘I thought you could use the company. It’s lonely at the top.’
The executive director, a nice older woman, was vastly amused by my explanation. She simply asked me not to pick any more locks.
Over the day, I overheard at least twice co-workers discussing how anyone else would have been fired, on the spot, for breaking into her office. But my boss took it for what it was. A simple prank. I showed no sign of guilt or attempt to deflect blame since eighteen-year-old me didn’t see it as having done anything wrong. I sold her on the innocence of the situation.
Now when I break into executive offices, I bill by the quarter-hour.”
“My boss and I were in Cancun Mexico, organizing a major international conference. We had the weekend off, and he and I decided it would be fun to go on an organized boat tour of the nearby islands.
The tour guides told us that the tours were free, but only if we agreed to sit through an hour-long sales pitch for a timeshare. Never having been to a timeshare pitch, I was intrigued. The catch? The resort only did timeshare pitches for married couples.
At the time, I was in a long-term committed relationship with my husband. My boss was also in a long-term relationship with his husband.
There was zero attraction between us, but I asked my boss, ‘Shall we just say we’re married?’
My boss cackled at my question, and we did it. We pretended to be married for an hour and got a free boat tour out of it. We both thought it was hilarious, and it was one of my favorite work memories.”
“His Face Turned An Angry Shade Of Red”
“When I finished grad school, I worked for a consulting firm for a few months before I landed my current job.
My horrible, condescending, boss went to an Ivy League school. He made sure he didn’t leave a chance to remind me of the fact, too.
My boss would matter-of-factly say, ‘Oh, you know in Harvard, we did things differently,’ or, ‘Oh, in Harvard, we reference so and so textbooks,’ and so on.
So one day, my boss leaned back in his chair, arrogance spilling out when he asked, ‘What do you think is the one thing Ivy League students have that other schools don’t?’
I was tired of him reminding me for the past six months about how I didn’t study at an Ivy League. Plus, I was sick of my boss treating me terribly.
I shot a dirty look across the room and said, ‘Hmm, let me think. A massive loan, perhaps?’
I watched as my boss’ face turned an angry shade of red, and I floated back to my cubicle happy and content.
I didn’t get fired, but I thankfully had another job offer waiting for me.”
“They Laughed About It For Hours”
“When I was an eighteen-year-old private in the military, I found myself in a new position driving the company commander around in a military Jeep.
At the time, we were completing training missions in the field. The commander sat in the passenger seat, and three sergeants sat in the back seat. On this particular day, the commander was in a great mood.
He turned to me and asked, ‘Isn’t it wonderful the government pays you great money, and all you have to do is drive a Jeep?’
I responded, ‘Of course, but isn’t it wonderful they pay you so much more to just sit there?’
The sergeants laughed about it for hours.”
When Risk Paid Off
“The craziest thing I ever said at a job interview surprisingly got me hired.
I was interviewing for a job in the program planning department for the New York State Department of Transportation.
My would-be boss explained, ‘We need to hire someone who absolutely won’t be intimidated by the bigwigs in the company. Far too many executives visit the office, and I need someone who knows how to handle them.’
‘Yeah, no problem,’ I replied.
‘Are you sure?’ he asked. ‘Can you tell someone important something they might not want to hear?’
‘Absolutely,’ I said. ‘For example, did you know you’re really short?’
My boss busted a gut laughing and I got the job. This guy interrupted my second interview the same day, which was taking place down the hall. He burst in to tell the interviewer she couldn’t have me because he already had dibs. He was a fabulous boss and a great friend.”
“I Decided I Wouldn’t Be Returning To The Job”
“A while back, I was out on medical leave. When I was out, something happened at work and I was written up for it. Yes, my boss wrote me up for something I couldn’t have possibly done since I wasn’t in the office. I was out recovering from surgery.
I tried to argue with my boss, and I explained to him how the situation wasn’t fair because I wasn’t in the office.
He countered, ‘Just sign the write-up so you can get back to work.’
I angrily replied, ‘No, please call human resources and get them down here.’
He was insistent I sign the write-up, but I told my boss no again.
I explained, ‘If you don’t want to call HR and get them down here, I will go up and talk with them instead. Your choice.’
My boss rolled his eyes, tore up the write-up, and tossed it in the trash.
After this, I decided I wouldn’t be returning to the job. My boss and I butted heads on several other occasions, and I was done dealing with him. Only two months later I quit.”