My Bad Boss Contest, 2008

World Class Bad Boss, Leona Helmsley

Have a really bad boss story to tell?  Are YOU a really bad boss?  The voting for the My Bad Boss Contest for 2008 is now closed at, so you’ll have to wait for next year’s contest if you think you’ve got what it takes!  This year’s winners received an all expense paid vacation for a richly deserved break.  One  winner’s story is like a page out of the SAUSD’s playbook when the Boss gets some bad news from a subordinate.  Disappointment turns to malicious retaliation and demotions.  Yummy petty vindictiveness against the powerless!  😉

Joan of Kansas wrote of her Bad Boss in, “I Didn’t Realize I Could See into the Future”:

Several years ago when I was the office manager at this company My boss asked me to organize an outing for our employees and I agreed. I felt an evening at a major league baseball game would be ideal for everyone.
I set the date for about two months out, getting a reduction on tickets for a group, getting a set amount of cash to give each employee so they could purchase snacks, organized carpooling, handing out tickets, etc.

The date arrived and it rained! My boss informed me that I had picked that particular date because I knew it would rain! My title changed from Manager to Assistant Manager and I was given a small reduction in pay.

A few months later, he asked if I would like to organize a picnic. I told him no. He then informed the Board that I refused to organize an employee picnic!


The other winner, Hillbilly Business Practices: 101  reads like a Jerry Springer episode with a tragic ending.

Often the ambulances had “mechanical problems.” My boss bought them used and abused and literally duct-taped them to stay together. One cold, Christmas day, I agreed to work for another employee so she could spend time with her kids for the holiday. All three ambulances were experiencing problems (1 had no lights or sirens, 1 had no functioning brakes, and one had no heat), and we were left to pick the lesser of three evils to take out on calls. My partner and I chose the ambulance without a functioning heater and had to fib to our patients regarding the frigidness of the ambulance. (Looking back, I suppose I could have stuck my head out the windows and made “Woo-Woo” sounds.)   Read the rest

If Bad Boss stories are your thing, then you’ll have fun with the Workingamerica site.  You can read all of the winning Bad Boss Stories—from categories like Scrooge Boss, Creepy Boss, and His Royal Bosiness –


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