Nightmare Bosses

The worst manager stories I’ve heard in a decade-plus of writing a workplace advice column.

Collage of angry bosses.
Photo illustration by Slate. Photos by Thinkstock.

Executive Time is Slate’s pop-up blog about bosses.

In the more than 10 years I’ve been writing the workplace advice column Ask a Manager, I’ve heard about some really bad bosses. Really bad ones. Picture the worst boss you’ve ever had, and these still might be worse. We’re not talking garden-variety incompetence here. We’re talking wedding-crashing, organ-pilfering, horse-murdering bad.

I’ve pulled together the eight awful boss letters that still give me nightmares. I’m going to ease you in (somewhat) slowly, but they get pretty horrific by the end of this list.

The boss who wants 20 percent of your salary from your next job

Ideally bosses invest in your development and help you build the skills and connections that will lead to your next job. But this one thinks that makes him entitled to a cut of your next salary:


I recently told my boss that I am looking for a new job, and that I would be leaving his company within four weeks. When I had a few offers, I met with the boss and discussed them with him, especially since one of the offers is a current client. He said that he wishes me well and that he will waive adherence to the “non-compete” clause, as the client is not changing any services with his company. A few days later, my boss calls me and says that he feels that it is fair that I pay 20 percent of my new salary as a conversion fee to his company. He said that it was because of him that I was able to interact with the company, and most recruiters charge 20 percent of the new salary as a fee.

The boss who wants help hiding his affairs from his wife

Being an assistant can mean you learn more about your boss’s personal life than you might want to know … but this guy has enlisted his assistant to facilitate his affairs and hide them from his wife:


My boss is having multiple affairs. I am his assistant, so I know about all his visitors and his schedule. He is married, but he often has visits from two different women, and he outright told me to never tell his wife about them. When either of them visit, he locks his door and tells me he is not to be disturbed. This happens almost weekly.

He sometimes asks me to book local hotel rooms for an hour or an afternoon, and he sometimes buys jewelry and flowers for the two women he sees regularly. I know this because he sends me out to pick up the jewelry (which I later see them wearing) or asks me to have the flowers sent to them. He never does anything like this for his wife. One of the women just had a baby who is named after my boss and has his surname.

One time, his wife showed up for a surprise visit to take him out to lunch, and he directed me to lie that the woman who was in his office was there for a job interview. He also submits expenses from his business trips (where he has traveled alone) and I have to re-calculate everything because he has upgraded the company-provided hotel room to a better one on his personal credit card and bought breakfast for more than one person the next morning. When this happens, he tells me he had “company.” There was also an incident where he came to work panicked because he said he accidentally used his company credit card at a strip club. He sent me to retrieve it and pay his tab with cash, but the address he sent me to was actually a massage parlor.

The boss who crashed a wedding

People sometimes agonize over whether to invite their boss to their wedding. What if you decided not to and he showed up anyway?


I’m an executive assistant. My boss … went to a coworker’s wedding because he had a question about something and she was the only one who could answer it. One of the groom’s relatives is a police officer and she had to escort my boss out because he wouldn’t leave. He tried to have the coworker written up at work over what happened, and she ended up quitting before she left for her honeymoon.

The boss who showed up while an employee was having chemotherapy

Speaking of showing up at inappropriate places to ask work questions, when this person was diagnosed with cancer, her assistant manager decided to show up at her chemotherapy sessions:

Recently while I was having chemotherapy, Ned showed up at the clinic and started asking me about work matters. I was completely surprised that he even knew where I was and that he was asking me about work on my off-time. The things he was asking about were not emergencies or work with deadlines. … I have asked the clinic not to admit Ned, but sometimes he comes in anyway or waits until no one is looking before he comes in. There have been times when the nurses have asked him to leave or told him to get out of the room I am in. Sometimes he lies to them and says it is an emergency, and one volunteer told me Ned told the nurse on duty that he was family. … His behavior is stressing me out even more than I already am.

The boss who read every email employees sent … and put cameras in their offices

Lots of people have worked for micromanagers at one point or another, but this boss took lack of trust to a new and deeply paranoid level:


One of the first things that alarmed me was that I learned the company’s CEO has our email system set up so that he is automatically blind copied on every single email that is sent out from a company address. … They also recently installed security cameras that include audio in each of our offices. I am fine with having video surveillance for common areas, but it feels odd to me that my boss could be watching me from his office at any point in the day without my knowing. It isn’t that I have something to hide, but sometimes on my lunch break, I close the door to take a personal call, and now I feel like there is nowhere to get any privacy. … Although my boss repeatedly tells me (almost as if he senses my apprehension) that I am “the very last person” he’d ever be watching or be suspicious of and that I am far from the reason he is taking such precautions, I feel very strange knowing that I have someone invading my space to that degree.

The boss who threatened to fire people if they didn’t sign up to be a liver donor for his brother

This boss must have desperately wanted to help his sick brother—but apparently forgot that you can’t demand that employees hand over parts of their bodies:


The owner of the company has a brother who needs a liver transplant. Two weeks ago, a company-wide memo went out that all employees would be required to undergo testing to see if they were a suitable liver donor for the owner’s brother. No exceptions.

Last week at the branch the owner works out of most of the time, his assistant went around to schedule days off for everyone so they could go get tested. People who declined were let go. … I’m in remission from cancer. I’m ineligible to donate and any kind of surgery would put a major strain on my system. Even if I was healthy, I would still object to possibly being forced into donating an organ just to keep my job.

The boss who let an employee’s horse die

One of the saddest letters I’ve ever received was from someone whose friend was taking care of her horse, discovered the horse was seriously ill, and tried to reach her at work since the vet wouldn’t proceed with treatment without her authorization:


My friend explained how dire the situation was and my manager told her he would let me know immediately. Except that he didn’t. … Unfortunately, in the three hours between my friend calling and my hearing of it, my horse’s heart rate had shot over 120 beats per minute. That 120 mark is used as an indicator that recovery is very unlikely, and I made the choice to have her put down.

I asked my manager why he hadn’t let me know what was going on and he said he was going to let me know at lunch time (approximately five hours after the call came) and I could leave then. … The kicker in all of this? That morning, my manager had me hosing walkways because he “didn’t have anything else for me to do.”

The boss who made an employee leave a work note at a grave

Think it’s bad that your boss won’t stop calling you when you’re out sick? (It is.) This boss told an employee to leave a work note at the grave that he expected a bereaved colleague to be visiting:


Three weeks ago one of my coworkers lost a relative. She has been off work on bereavement and family leave. Our boss isn’t happy with her being off for so long. Since it is out of his control and he doesn’t get to approve or deny her leave in this case (the HR department is in charge of that) I have been doing my best to ignore him whenever he complains.

Last week my boss gave me an envelope with my coworker’s name on it and told me to leave it at the grave of my coworker’s relative. He said it was a condolence card at first, but I didn’t buy it because our work had already sent a card. When I asked him about it again, he said it was a note with some work-related items only she knows about and he needs answers ASAP and she won’t answer her (personal, not work) phone when he calls her. He gave me directions to the cemetery and everything.

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