Why Some Bosses Suck
By: Tim Denning
Tags: Leadership, Self Improvement, Life, Startup, Entrepreneurship

Every morning I’d walk up the hill of the busy city streets trying not to be late. Late, to my bad boss, was anything past 8:59 am. He’d sit at his desk with his beer gut, drinking coffee and tapping his metaphorical stick against the desk while simultaneously looking at his watch.

He wanted people to fear him and attendance of his strict times was one way he played out this adult fantasy. Some days he looked like Voldemort with his death like appearance. See, he wasn’t an old guy based on his age, but the way he looked told a completely different story. His smile showed off his off-white teeth and deathly smile. His hair was long, tired and grey. His skin was dry and flaking and he’d spent one too many summers mowing the front lawn of his mansion while forgetting to contemplate the meaning of life.

Some days he wore a nicely kept suit and his favorite Williams boots. On Friday, you’d get to see who he really was. He’d wear his wife beater chequered shirt and his brand new Nike shoes. It was like he was watching himself in the movie Back To The Future and reminiscing about his teenage years to understand what went wrong in his life. He wasn’t fooling anyone. During one of these Fridays, his shirt was rolled up. I could see an arm full of tattoos which for a supposed corporate warrior from back in the day, I was surprised by. He then told me he was covered all over in tattoos. This was the first sign I’d come across that might give me a clue to his past. The mystery of why he’d become a bad boss intrigued me even though on some days I thought to myself “Who cares, just fire his ass by quitting.”

He was a bad boss and I’m convinced that deep down he knew it. That was why, strangely, I felt sorry for him in a way despite the fact he treated me like a piece of shit that he found on the bottom of his Williams boots and was stuck with. When I’d sit in meetings with him, I couldn’t focus on what he was saying. This part is important: what made him a bad boss was that it was all about him. His goal was to build his sandcastle empire and hope that no one would realize it was made out of sand and could be destroyed with a freely available commodity such as water.

Everything he did at work was about building his empire. He’d pretend that he cared about people and their career dreams but never actually go to the effort of finding out what people cared about. It was as if he’d read a book like ‘Tribal Leadership’ by David Logan and wanted to show off the cover of the book to everyone he met, and show the way it sparkled, without ever actually reading it or sharing with anyone what the book meant — or putting into practice some of the lessons.

The part that made him a bad boss was something I’d never experienced before. He’d walk out into the middle of the office and talk loudly about how he loved to fire people. He’d say “Today’s a good day for a sacking isn’t it?”

Or “I haven’t sacked anybody today. Would you like to be sacked?”

It was like I was watching an episode of Seinfeld and laughing along and then realizing that I’d just laughed at a joke about people dying in gas chambers under the reign of Hitler.

The first few times he did it, I laughed. Then I thought about what I was doing and remembered that laughing was a subtle way of telling him, my team, and the poor people he was yelling at, that I agreed with him. Agreeing with him, in my mind, was like telling the devil himself that I’d like to work for him for the rest of my life and do his evil work with a smile.

Sacking people to him was normal. Humans were disposable machines that had an expiry date. His goal was to use you up until you’d had enough of the verbal abuse that he dished out to you, and finally quit. This wasn’t just a figment of my imagination although for the first few weeks I thought it might be. One summers afternoon he took myself and the other two leaders into a room. We’d had a pre-scheduled meeting booked to talk through one of his plans that none of us believed in, but knew we had to listen to. For the record, we didn’t believe in it because he’d told me in another chat how he planned to fire several other leaders so he could control more areas of the business and eventually become a C-Level Executive at the company. He knew he’d have to walk over dead bodies to do it and that excited him in a way. He didn’t do the shooting of his fellow leaders himself; he got others to pull the trigger for him while he sat back and watched with a huge smile on his face.

Anyway, back to the story. In this meeting, there was a bit of banter back and forth. I tried to relax by eating the Barbecue Shape Biscuits that were in the middle of the desk and getting the delicious red flavoring all over my hands. This was a weird thing for me to do because I hadn’t eaten these biscuits since I was a child mostly because they were unhealthy. What can I say, working under a bad boss took its toll in weird and sometimes strange ways. As I took another bite of a Barbecue Shape Biscuit, the conversation went in a strange direction. He started talking about sacking again, but this time he went the extra step. He spoke about what would happen if one of us ever dared cross him and go him for unfair dismissal.

Image Credit: Serena Loder

It went like this: If he fired you, you’d take the four weeks of pay he so kindly gave you (cause he’s a great guy, remember?), pack your shit and get out of his f**king office. They were your instructions. If you chose to disagree with his decision and expect to be put on a performance plan beforehand, and then used that as grounds for an unfair dismissal, he’d use one of his off the shelf strategies that he learned from his previous job. He explained to us that no matter how perfect you are, everyone makes mistakes including him.

For a split second, I thought he might be about to show a tiny bit of his human side.

Then he went back to his usual self and said: “And I’ll find a couple of things you did wrong, by going through your emails, and use them against you at the unfair dismissal tribunal.”

This was his ego talking again. I left the meeting room as soon as he excused us like an angry school principal who just cracked the whip, and went back to my desk. I thought about what he said and I kept coming up with the same question: “But why is he a bad boss? What’s making him be this way?”

The only way I could describe the way he led was “Inhumane.”

It wasn’t enough, though, to draw this conclusion. I wanted to understand why he was a bad boss.