Life Lessons From a Bad Boss

“Do you have a drug or gambling addiction?” my new boss asked the first time I met him. 

He just laughed when I replied, “Are you allowed to ask that?”  

Then he asked if I came from money. 

“Money?” I repeated.

He said he thought I might because I looked polished. 

I was surprised. Polished is not a word anyone had ever used to describe me before … or since. 

“Do you come from money?” he asked again.

I mumbled something about being from a small farming family. 

“So if you got into trouble with money, is there anyone who could bail you out?”

Another odd question, but then the whole conversation was odd. 

What makes a bad boss?

There is a range when it comes to badness in a boss. On the one side, there is the type often depicted in books and TV shows. Bumbling yet affable, delusional about their greatness and quick to pass the buck, but somehow still likable.

On the other side, across a spectrum the size of the Grand Canyon, is a manipulative, cruel person who is completely lacking in empathy or conscience. The kind of person who likes nothing more than to see people fail. 

This particular boss wasn’t completely here, but he definitely had at least one toe on this side of the bad boss spectrum.

Kind of like Don Draper without the style.

Frank Underwood without the brains. 

Picture Mr. Burns with hair plugs. 

It might seem like he was just awkward and clueless, merely lacking in people skills. But he wasn’t. He wasn’t just an inept clown who built a business on credit cards and luck. He was (and is) a successful businessman who owns a yacht, lives in a 10,000-square-foot house, and attends church every Sunday. 

Looking back after a decade of reflection, our first interaction was not a subtle warning. It was an enormous red flag flapping in the wind with the word RUN! printed on it in big yellow letters. I should have walked out after he quizzed me about addictions, but I was naïve and at this point in my life, nothing mattered but the rent.  

Besides, I figured I had already experienced a tough boss when I worked in advertising in New York. He once called me, “a waste of skin” after I made a rather large and admittedly dumb mistake in an important piece of copy.

What I have learned, however, is tough does not equal bad. 

 My New York boss was definitely tough. Never warm or friendly, he left office parties after one Scotch and five minutes of painful small talk. He yelled a lot and regularly used language frowned upon by all religious denominations and my mother. He was gruff and sharp and a little scary.

But he also handed out raises and bonuses willingly. He was always quick to praise. He let the whole office leave at 1pm on Fridays in the summer, long before that became a thing to keep Millennials on the payroll. He paid for any classes or extra training and pushed people to be better even if it meant good people left his company. His expectations were high, but within reach. 

He made me more resilient and tenacious with his blunt, but usually fair, honesty. His people were nervous to disappoint him, but fiercely loyal.

I left that job better, with stronger skills and a clearer belief in myself. 

The bad boss had the opposite effect. He was cheap with money and with praise. He wanted you to feel small and was always looking for ways to knock you off your feet. He believed the more he ground down a person’s self-worth, the harder they would work. 

But unlike my New York boss, he was smooth and charming. He never raised his voice. He would dish out casual cruelty with a smile on his face. If you performed well, he would politely remind you of a time you failed. If you accomplished a goal, it was met with indifference. He cherished gossip and encouraged competition by letting you know when you didn’t measure up to a colleague. 

His entire management system was based on finding the place where a person might be fragile, like how you look for the weakest part of a branch you want to snap in half. 

I found out later that he always asked about addictions because he believed “addicts are easier to control.” 

At first, I was shocked he would admit that, but it would soon become clear. He believed he stood on top of everyone; untouchable on his pedestal.

Luckily, this meant his intentions were right out in the open. He didn’t quietly figure out your vulnerabilities and then shrewdly use them to destroy you. That’s the only thing that kept him from being fully on the bad side of the boss spectrum. His intentions were obvious – flagrant even – to anyone who wasn’t duped by his charm. You have a fighting chance when a predator is in front of you; if it’s hiding behind a tree preparing for ambush, you’re toast.

I left that job after a year, a little worse for wear, but definitely not snapped in half. I left with hope and a determination to find another good boss. A boss who wants people to succeed. A boss who knows when people feel valued, they do a better job. A boss who will call you to the carpet for a mistake in an effort to make you better. A boss who gives a damn about people. 

I wanted to work for someone like my New York boss again. A little scary, yes, but whose door I walked out taller than I walked in.


~Christine MacLeod