I worked at a 4 person interior design firm in NYC for a few months during the recession. My boss and firm owner was a total psycho. She made us sit classroom style, facing her so she could see what we were doing at all times. Every day she would yell at us and threaten to not pay us the next pay cycle or fire us. One afternoon she made us stop working for 3 hours and write an essay explaining the 5 reasons why she should not fire us. We had to then present the reasoning front of everyone else. We had an intern who she fired because she was too ‘star struck’ when meeting a C-list celeb client. She also once lectured at us because we didn’t personally serve her a cupcake a promo event. Once I had a pair of $50 shoes and a $3 necklace from Aldo delivered to the office and she flipped out because she claimed HER money was going to fund MY wardrobe and she could not afford such items. She would also search our work emails and internet history every night to see if we were talking shit about her. She would make us thank her for allowing us to wear business casual clothes and not have to pay for dry-cleaning. She made me work on Valentine’s day because she was jealous she has still single and I had just gotten engaged. These are just the highlights, I could go on and on! Not sure how I survived that one.

OP, your boss sounds like mine sans the alcoholism. She constantly gossips about other staff to me, routinely badmouths her boss and our VP a daily basis. And yes it’s usually very personal details about someone’s health or family situations that I do not need to know. Just the other day she told me our co-worker withdrew his 401K to fund his son’s college tuition. I mean really, really inappropriate stuff.

In addition she never gives me any real feedback, usually she nitpicks my work to death and never ever says thank you! She always complains that she is so much smarter than everyone else and that she works so much harder, yet she comes in at 930 and never leaves past 430. She has never given me a formal performance review. She also likes to keep me out of important meetings and talks over me when we do meet with clients. When I have asked for specific direction, she gives me a very vague answer and then blows up because I was unable to read her mind. Most of the time she talks to me it is to brag about her travel plans, her daughter’s tennis awards, her beach house, etc.

A prior boss decided to surprise a co-worker for his birthday with a male stripper. Because the stripper didn't take AmEx he made the Admin exec put it on her personal card. A few hours later, 3 wallets were missing.

I left shortly after this little display. (I was at a coffee shop across the street, as I wanted zero part of this)

When they are bad, they are sooooo bad.

I had the laziest boss when I got out of college. She got into the office at 10, but wanted me there at 8 to turn on her computer and turn on her lights and answer her phone (I was supposed to say "she's on the other line.") She'd routinely take 2+ hour lunches, and come back and talk about totally inappropriate things (where she got her bikini waxing done, how much it hurt, or one time talking about whether to buy a pushup bra, etc.) She stayed past 5:00 pm maybe twice in the year I worked there, but mostly had to meet people for "work" and would leave at 4:30. She'd get angry if I wanted to come in late or leave early (no one to cover for her office lights, computers, etc.) I once left early and didn't tell her--because she wasn't there to inform--and she b*tched about ME on facebook... I was so steamed!

Oh, and she asked me to pick up her dry cleaning. I just stared at her like she was speaking another language and she dropped the subject.

Sorry for typos above, my iPhone autocomplete!

I have a terrible boss. He is a terrible passive aggressive manager, gossiping about staff, divulging personal information (including mental illnesses) of people be supervised. He bad-months staff to those who report to them, asks multiple people to do the same task consistently, and is an alcoholic.

At the same time, he is so incompetent it lets me get away with mediocrity, and I don't burn the candle at both ends. I stay where I am for the money and benefits, particularly while the little ones want more time with me.

Would love to hear bad boss stories to make me feel better about mine!