About ten years ago I worked for a local ISP. Several management issues just generally, but my manager in particular was awful.

Three employees, with a board of directors of five people. The board would convene even for routine tasks like writing a $200 check to buy some modems.

One of the owners had another business that shared an office with us. He did our books. He'd routinely be on the phone with other owners complaining about how he wasn't sure he would be able to make payroll - within earshot of the entire staff (no walls or even cubicles in this open floor office). Mysteriously, when he quit in a huff and someone else took over the books, we were in the black in under 30 days.

I initially interviewed for a tech support position. This mostly involved talking to customers and helping them set up or fix their network configurations. I interviewed with the person destined to be my manager. His approach to the interview was to have me draw random shapes on a piece of paper, and then describe them to him. He drew what I told him ("a circle... about 1 inch from the left margin... about 3 inches across...") and the objective was to see how accurate his copy was. I went along with this partly so I might get the job, and partly out of a baffled curiosity as to what the point might be. It turned out that he was testing my ability to describe things to people who can't see what I'm looking at. Never mind that configuration screens look nothing like what I drew, and were described typically by their labels (words) not shapes or positions.

After I was hired, I was given a Linux machine to work on. Almost every customer was using either Windows or a Mac. I had neither to work with for the first month or so. I was also supposed to do certain tasks that required admin access on our servers (i.e. root-level access). But he forbid the main tech guy from giving me this access, meaning I had to interrupt that guy constantly to do things for me. Inside a week, we solved this problem: I was given root access surreptitiously and whenever the boss came around I'd switch to another screen that wasn't logged in as root.

The manager's job seemed to consist of 4 things:

1. Taking long breaks to read playboy.com and Cigar Afficionado magazine. Whenever a customer showed up, everybody knew to double check his monitor to see if playboy.com had to be closed.

2. Browsing catalogs of cowboy boots online, and buying a pair every now and again. These boots were well known in the office, because they'd always be perched up on his desk while he was reading Cigar Afficionado.

3. Going on half-day "business meetings" to one of our clients, conveniently owned by a couple of his high school buddies.

4. Calling his father to beg for another loan to pay his mortgage.

Whenever someone walked up behind me, I could tell if it was him by the smell of his breath (I've smelled better from a dog's mouth). It didn't take long before I instinctively held my breath whenever I heard footsteps.

He resigned a couple of times via email, then just showed up the next day like nothing had happened. The third time he did it, they changed the locks and told him to pack his desk. We had a special lunch to celebrate it.