On April 10th, I hosted The Daily WTF: Live! in Pittsburgh. It was a blast. We had a great crowd, and some great performances.

Our final story is another one of my own, and this one is about… the worst boss ever. I mean it, and in this story, I can prove it. This is also arguably my first interaction with a real WTF.

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This brings our season of TDWTF:Live to a close. I had fun hosting and recording these stories, and I hope you had fun listening to them. Next Thursday will return to your regularly scheduled WTFs.

And since Paula is freaking out at the moment, pop over here for the comments.


At the Daily WTF, there’s one kind of story we get a lot of submissions for that we don’t often run, and these fall into the category of what I like to call a Bad Boss Story. There are three reasons we don’t run bad boss stories. The first one is you never really know if it’s truly that this boss was a terrible boss, or it was just somebody that has sour grapes. ‘Cause sometimes, you read them, and you’re like, ‘You just didn’t like the guy. It’s not that you had a bad boss, you just didn’t get along.’

The other reason is that there’s nothing IT specific about any bad boss story. Everybody’s had a bad boss. Raise your hand if you’ve had a bad boss. Pretty much everybody. And that’s one of the other reasons we don’t run them, there’s nothing IT specific. But the main reason we don’t run a lot of bad boss stories, is because I had the worst boss.

And I can prove this, and I’m about to in the next couple of minutes, I’m going to prove that I had the worst boss.

My story starts a little bit like Mark’s. I was graduating college and it was just around the DotCom bust. And I did not want to, after graduation, go home and live with my parents. I was very, very opposed to this. I happened to have some friends who were generous enough to let me impose upon their closet. I lived in their closet for about six months, so I really wanted a job. I was not very picky about the job, there was nothing really going, so as soon as I found a job- and it was an IT job. I was doing stuff with Word and Excel, not programming, but it was an IT job. Y’know what, it’s an IT job, I’m going to take it, and I don’t care about any of the details.

And that was my first mistake.

So, I walk in on the first day, and the Big Boss, Tom, the owner of the company is there to greet me. And I’m kinda overwhelmed almost instantly by Tom. Because first, Tom was so orange that Tropicana has sued him for trademark infringement. It wasn’t just, like the bottle-tan, Jersey Shore orange, because he had grey hair, and he wanted to ensure that he didn’t have any seams, so he would work the tanning lotion into his scalp, so he had this fringe of orange hair all the way around.

And that was just the first thing you notice. The second thing you notice is that he’s a very grabby boss. The very first thing he does is slap his hand on my shoulder and give it that… squeeze. “Hows everything GOING?” Ugggghhhhh.

But everything was going pretty well, because I had a job, and in a couple weeks I was going to be getting a paycheck. Everything was going well. I was enthusiastic.

I learned, very quickly, Tom was not- as much as he pretended to care (How’s everything going, SQUEEZE SQUEEZE SQUEEZE) he didn’t really care about his employees. So, when he needed you to work two weeks straight, 16 hour days, you were 16 hour days for two weeks straight. There was no compensation. There was no buy you a pizza. He didn’t buy you dinner. You just did that, because that was your job.

And again, I was still kinda happy to have a job, so I would drag my ass in at 7 in the morning, and leave at around 10 PM at night, and I’d do that for two weeks straight, three weeks straight- no, actually, after the third week, I needed to travel to a different location, so Friday night after the third week I get Saturday, but then Sunday I have to go drive ten hours away to the other side of New York State, which is where this was based.

So, that’s the next thing I learned about Tom. But y’know what? That’s still not why he’s the worst boss I ever had.

I learned a few other things about Tom, over time. First off, Tom didn’t have a good sense of where he was at any given moment, or what his purpose there was. One day, I’m sitting in the break room with one of my co-workers, and Tom comes in- and he bursts, he just explodes into the room, full of energy. There is a reason why he has come into the employee break room. He is looking for someone, to tell them something, and he bursts in, and he’s about to do it- you can see him winding up, you can see the gears turning. Then he looks at my co-worker, and he looks at her tights, which have this check pattern on them, and he says, “I just want to play tic-tac-toe on your legs.” And then he turns around and walks out. And we just take a long moment, I look at Paige, she looks at me, and we ask, “Did that just happen?” and the answer is yes.

Later that day, I was getting a cup of coffee and all of the sudden, THUMP “How’s everything going?” Ugh.

Little later than that, we actually learned another fact, didn’t know it at the time. Tom, and his wife- who worked there, she was actually the Vice President- always a sign of a healthy company- they were swingers. And they did invite some employees to some parties at points. They did invite some employees to parties at points. I don’t know whether to be happy or insulted that this never happened to me, but y’know? None of that is why Tom was the worst boss I ever had.

Tom was the sort of boss that really loved to have pep talks. Every Friday, at 4:30, you did not go home, you went to the mandatory meeting. There was no excuse that would get you out of that meeting. There was no excuse that would get you out of that meeting. If you called in sick that day, you couldn’t get out of that meeting. He really wanted to give you your pep-talk. And his pep-talk were absolutely content-free, but you also learned another thing about Tom.

Friday, at 4:30, Tom would be dragging ass just like the rest of us. You’d see him in the hallway and he wouldn’t go “THUMP How’s everything going?” He’d be, “eh”, it’s Friday, at 4:30. But right before the meeting, he’d go into his office and close the door. And then the door would open, and (sniffling sound) he would come out and he was READY TO PEP YOU UP.

But Friday at 4:30 coke fueled meetings were not why Tom was the worst boss I ever had.

One day, I come into work, and Tom’s not there. Which, is actually a pretty good thing. Everybody’s pretty happy about that. Nobody’s upset that Tom’s not there, until Chris, the Ops Manager, starts running around frantically to everybody. “There’s a meeting during lunch, and you HAVE to be there. Don’t go to lunch, doesn’t matter if you didn’t think to bring a lunch, you HAVE to be at this meeting.”

I’m like, “Oh god, what’s Tom gonna do to us now?” Well, as it turns out, Tom wasn’t going to do anything to us, because Tom had drained the company’s bank accounts, run off to Connecticut, left about two dozen contracts unfulfilled, and was being hounded by lawyers. The content of this 12 o’clock meeting was “We don’t know where Tom is, we don’t know how to get in touch with Tom, but if Tom contacts you, let us know. The State Troopers would like to have a conversation with him.”

And that’s STILL not why Tom was the worst boss I ever had.

If we rewind just a little bit, keep in mind I was just happy at this point to have a job, but if we rewind just a little bit… One day, I’m standing at a urinal, going to the bathroom, as one does, and all of the sudden…

THUMP SQUEEZE SQUEEZE SQUEEZE. “How’s everything going?”

There’s so many witting things that you can think of after the fact, that you could have said or done in that situation, but when it actually happens to you, everything just shuts down. EVERYTHING shuts down. You just stop. You wait for it to be over. You wait for Tom to leave. You wash your hands. You just… cry briefly. And then you remember, at least you have a job.

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