Horrible Bosses I Have Known

At one time or another, we've all been trapped in this particular circle of hell

Photograph by Getty Images/Big Cheese Photo RF

I've been doing some research on bad boss behavior for a novel (my first, and probably my last). From what I've read so far on the Internet, it appears that a young woman is less at risk of sexual abuse or harassment at a drunken frat party than she is from a supervisor in the average American workplace. Men have it better, but not much. Their ability to survive today's vicious corporate rat race depends in large part on how well their bodies tolerate high-octane mood stabilizers and mass quantities of Mylanta.

Last week, a friend of ours—a dedicated and experienced health care professional—got texted by her boss during her father's funeral. She was undoubtedly still in shock, as she attempted to text him back halfway through the rabbi's eulogy. A clear-thinking friend snatched away her cellphone and ripped off a huffy reply: "She's at her father's funeral! STOP TEXTING NOW!"

As it happens, the woman's boss knew perfectly well where she was. And, although the matter at hand was hardly an urgent one and could easily have waited until the body was in the ground, this boss chose to soothe his own immediate feelings of anxiety rather than bother with the usual social conventions of death and dying.

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I've been pretty fortunate when it comes to bosses, but I've also had a lot of jobs and a few bad apples were bound to fall from the tree and land on my head.


Some years ago, when I was first starting out in a new career as a social service case manager, I accepted an entry-level job that came with a three-month probation. During this period, I was not permitted to miss a workday—not for illness, death in the family ... nothing. About 30 days into the job, the sister of a very old and dear friend was killed in a horrific traffic accident. The funeral was scheduled for the following day in a town several hundred miles from my home in New York.

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"I'm sorry," I advised the boss. "I need to take tomorrow off to go out of town." I explained the situation and apologized for having to violate the terms of my probation.

"I'm afraid I can't allow you to do that," the boss said, in a voice half robotic and half Joan Crawford. "The rules are the rules." I wondered who it was she thought she was talking to.

"Well," I replied, "I'm taking the day off. You do what you have to do."

The boss ultimately backed down and I kept my job. I wanted to ask her what ungodly impulse had prompted her brief descent into corporate madness, but I opted to let it go.


About 35 years ago, I took a freelance job doing clerical work for a psychiatrist who ran a mental health clinic. In retrospect, it was less a job than it was a psychological experiment. The boss was truly off his nut, a living corroboration of the belief that all psychiatrists are crazy. I showed up for work every day not for the money, but just to see what this guy would do next.

One afternoon, for example, a colleague found him standing beside the office copy machine, muttering all manner of expletives as the machine spat out copies of the front of a business envelope.

"I can't understand," said the boss. "This isn't working." Seems he thought that if you placed an envelope in the Xerox machine, it would produce more envelopes. My colleague, rather than try to delve into his dementia, just backed quietly out of the room.

Later, the boss, in an effort to save some money, had me and my ex-wife move his giant marble coffee table from the office to his personal residence. It took us hours to move the massive thing and, naturally, we chipped the edge of the marble.

"I told you to hire a licensed mover," I said to the boss when he threatened to sue me for the damage to the furniture.

I lasted in this job only a few weeks, as the good doctor's eccentricities had clearly begun to lose their ability to astound and amuse. I imagine him still standing beside the copier, waiting for the envelopes.


When Dean Wormer sentenced Delta House to double secret probation, he let loose a demon on corporate America. An entire generation of psycho bosses now felt empowered to use this diabolical management technique on their poor workers.

After the editor in chief was let go at a business magazine I worked at in the '80s—he was a great guy—they replaced him with a nasty little prick named Todd. That's usually how corporate successions work. Anyway, Todd was very big on double secret probation. One day a reporter walked into my office and said Todd had just reamed him out about his work, telling him he needed to shape up or ship out. But Todd wouldn't tell him what was wrong with his work, what he needed to do to improve his work, or provide any timeframe for that required improvement.

"What am I supposed to do?" the dumbfounded reporter asked me.

The answer was obvious. "Throw a toga party," I said.

Shortly thereafter, I walked into Todd's office and quit. I so much wanted to fulfill my dream of telling a horrible boss to "take this job and shove it." But I just couldn't say the words, even to a schmuck like that. Probably why I never became a big boss man.

Tags: work

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