I’ve had several jobs over the years, with plenty of bosses. Some were great (I’m look at you, Linda and Matt), some were decent enough, and some… well… I’ll paraphrase a line from “The Leadership Secrets of Attila the Hun” which said:
Every boss has value, even if only to serve as a bad example.
So earlier in my career I wasn’t what you’d call, well, mature. I was still mentally in school mode, which meant try hard to make friends and be funny. So while I often amused my coworkers, sometimes I made comedic choices that weren’t in the best interests of my career. But, you live and learn.
Here are a few of my favorites.
- My very first real honest to goodness job was in midtown Manhattan working for a foreign credit organization. The big boss was a transplanted Frenchman with whom I never did seem to connect. He was conducting his annual charity clothing drive when he popped into the middle of a conversation I was having with some coworkers, and he asked me if I had any old clothes. Without thinking I blurted out, “Yes, but I don’t think they’ll fit you.”
- When I’d gotten passed over for a promotion to department head, after having performed as acting department head for quite a while, I turned in a resignation letter effective at the end of the day. My VP called me into his office that afternoon to tell me they weren’t accepting my resignation. My immediate response was to ask, “Then what were you going to do when I didn’t show up on Monday?” (They eventually offered me a different position elsewhere in what turned out to be a better career move.)
- The Project Manager of my development team resigned in the middle of a big project, and my director (with whom I did NOT get along) asked me to take over as acting project manager. (Acting, remember?) I asked him if he thought I was qualified to do the job, since I actually was interested in it. Without thinking twice, he said he did not. Not to be out-unthunk, I turned it down. “If I wanted to act,” I said, “I’d move to Hollywood.” Within a couple of months I became a director myself, and (separately) he was terminated and escorted from the building.