Last week, I posted "The 10 Dumbest Corporate E-mails of All Time." However, boneheaded emails are only the tip of the proverbial iceberg when it comes to lousy management inside large enterprises.

The following stories, culled from dozens readers sent me over the years, provide the best reasons I've ever encountered for starting a company rather than remaining with a big firm. Can you top them?

1. I hate to disturb you, but …

I was filling in for a co-worker who was having a baby by Caesarian that morning. The boss couldn't find a file and asked me if there was any way I could contact the absent employee to ask her where he could locate the file. I replied in jest: "Sure, I can call the hospital and have her paged." Ten minutes later, the boss reappeared at my desk and asked, "Did you reach her yet?"

2. It's all about the bottom line.

As a service to the community, my company donates food to the homeless. Shortly after my boss became director of this program, he determined that it was "losing money" because it took employee time to gather and deliver the food. In his next staff meeting, he asked: "Do you think there's some way we could charge the homeless for the food?"

3. Second prize: a set of steak knives.

Every month we had a "Sales Rep of the Month" contest. Each month, the winner just happened to be the daughter of the company's owner. The sales manager made a big deal about congratulating her, awarding her prize money at company meetings with her name on a plaque. The rep with the lowest sales was awarded a plastic chicken that he had to carry to every meeting for the rest of the month.

4. Maybe it was her evil twin.

Our boss decided to attend our Friday-evening sales meeting, which took place in the back room of a local tavern. She had a few too many and proceeded to make out with, dance on, and hug all of the male sales people. We finally sent her home in a cab after she face-plowed in the middle of the bar. To redeem herself on Monday, she publicly accused the entire sales force of making up stories about her.

5. Do as I say not as I do.

Every morning, my boss would hold hour-long meetings during which he'd show us videos about how to be a better leader. In every case, our manager was either weak in, or did the exact opposite of, the behaviors that the video recommended. After the video, he'd force us to have a 30- to 45-minute discussion on how "we" could apply the lessons that we'd learned.

6. A case of mistaken identity.

I was working at a printing company and one of my responsibilities was to proof copy. I had been on vacation and when I got back, the boss pulled me into his office and started berating me, asking how I could miss such obvious and stupid errors. After his tirade, I pointed out that the mistake had been made while I was on vacation. His response: "Well, it looked like something you would do."

7. Expect the unexpected.

My boss, who oversaw the cash management operation for a large San Francisco bank, would wait until one of the guys in the sales group would head to the bathroom. Then, while the poor unsuspecting guy was standing in front of the urinal, he would run in, wave his arms, and shout at the top of his lungs, "Why aren't you out on customer calls?"

8. Big brother is watching.

My boss became obsessed with the idea that one of his work-at-home employees wasn't actually working full time. He started driving by her house to take pictures with his camera phone as evidence. He even parked outside of her 9-year-old son's school ostensibly to observe her picking him up after school during work hours. Think about it: a grown man parked outside a school watching small children and taking pictures.

9. And while I have you here …

My boss could not decide whether he wanted to be our "leader" or "one of the guys." One day, after subjecting me to a session of inspirational talk, he asked for my opinion about something. I said, "Sure, why not?" He raised his shirt to display what looked like a nasty boil. I later found out he'd been ambushing staff all through the office to check out his boil … in the men's room, the stock room, even in the hallway.

10. Honesty is the best policy.

At our recent monthly review meeting, my boss showed a video about the importance of morals and ethics, and expounded upon such virtues as optimism, hard work, and honesty. The movie was very uplifting and motivating, but just before the lights came on, a final message ran across the screen: "For demo purposes only--illegal to use for training."

Readers: Have any bad boss stories to share? Email them to me or leave them as comments.

Published on: Sep 25, 2014
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