Business Pundit

I never heard of National Boss’s Day until yesterday. Did the National Boss Day people set up a hardcore PR campaign or something? This was simply not celebrated during my office days, which admittedly took place not too long ago.

In honor of boss’s day, which I am celebrating by almost being my own boss (with an obligation to provide you with excellent content), I create a list honoring the five worst bosses I’ve encountered during my career.

Boss #1: The Del Mar Fair Breast-Gazer

My first job ever was at a sausage stand in North County San Diego’s Del Mar Fair. Yes, I know what you’re thinking. My boss must have been thinking the same thing. He hired, monitored me, and fired me by talking to my breasts.

If you’re a woman, you know what I’m talking about. Some men make eye contact between breast oglings. This guy never made eye contact.

Boss #2: The Well-Meaning Absentee

This boss was cheerful and friendly during meetings. She almost always smiled. However, she did nothing to help her employees. If you wanted to talk to her face-to-face, you usually had to wait a week. She didn’t tell you how to get ahead, nor how you might be falling behind. She didn’t acknowledge your projects or good work. She was sweet, smiled, and did absolutely nothing to help.

She just didn’t seem to know what she was doing.

Boss #3: The Concerned Micromanager

This boss micromanaged by constantly monitoring his team, either by dropping in on them nine times a day (via seagull management), or by emailing a constant stream of questions about their work.

I don’t work well under these kinds of circumstances. I seize up and get so nervous that my productivity goes down.

Micromanager noticed my lack of enthusiasm, so he called me into his office, where he informed me that I struck him as the kind of person who didn’t have many goals in life.

Thankfully, he moved on to a different project where he didn’t have to deal with other human beings.

Boss #4: The Outshiner

This boss was incredibly concerned with creating a team that outshone her competition (the six other middle managers on the floor). She was all about numbers. If the analytics showed that her team’s numbers were top-notch, she would gain recognition and a coveted promotion.

So she drove us to build numbers without any further explanation or motivation. This led to an embittered, alienated team effect not augmented by the fact that other teams performed better than we did every quarter.

Boss #5: The Backpedaler

An organizational nightmare can disarm even the most skilled of managers. This manager, an otherwise excellent communicator, was no exception. He told us something different almost every week. When someone brought up what he had said the week before, he would claim he never said that. So his employees spent most of their time floating in informational mid-air.

Boss #6: The Bad Hippy

This unsuccessful entrepreneur takes the bad-boss cake. Not only did he operate an illegal shop, hiring people as contractors with stringent requirements that would legally entitle them to salaried pay, but he did nothing to insulate his contractors from his wild mood swings, chewing out an unlucky few while lavishly praising others.

He also looked like a hippy–hence the title–disproving my long-held belief that peaceniks were also peaceful.

Anyone else have a bad boss tale to share?