Clueless, Comical, and Cruel Bosses

A month ago, I asked readers for examples of clueless, comical, and cruel bosses. You did a wonderful job–via comments and emails–of sending in over 100 awful actions. Here are the list of my favorites–the worst of the worst.



You may recall that, about a month ago, I asked readers for examples of clueless, comical, and cruel bosses. You did a wonderful job–via comments and emails–of sending in over 100 awful actions. I promised I would list my favorites–the worst of the worst–here. It took me longer than I expected to get to it, but I finally did this week. The top 14 are presented at Huffington Post as a slide show, with all sorts of bells and whistles (you can vote on each boss and other things). The call it “Horror Stories About the World’s Worst Bosses.” The first slide is pictured above. The caption is:

1. “Giving the first employee of the month award to himself.”

Below are the other 14 I sent them (they cut one) followed by a bonus example:

2. “Showed appreciation by giving an employee an ipod (except he’s deaf).”

3. “My first boss was the founding partner of a mid-sized law firm in Boston … .He used to come in every morning, vise-grip my head with his hands, kiss the top of it, and say ‘hello my luv, ho-e-you, ho-e-you’. Then he’d proceed to shred me all day long. His best moments were after I was sick and lost too much weight, used to walk around screaming ‘where’s the damned stick with t*ts?.’ Really. I worked for him for 15 years. Then I went to one of the biggest firms in Boston, worked for the chairman of a big department. He started farting really loud when they made him not be chairman anymore. The special times were when he got really mad, and people would try to talk over it, and he’d push even harder, and they’d jump an octave.”

4. “A very attractive female direct report was working while sick. He shouted “! You’re looking mighty ugly today!” Saying it once wasn’t enough. He said it very loudly about 3 or 4 times.”


5. “My wife’s boss eats pork chops in team meetings, then picks her teeth.”

6. “He kept me from conferring with the doctors that were treating my mother for a brain tumor.”

7.” I had one boss who used to call meetings, invite a bunch of people, and of course there was no agenda so we didn’t even know what we were supposed to be discussing. Then, just as everybody arrived, his cell phone would go off and he would excuse himself to go take a lengthy personal call while the rest of us just sat in the conference room twiddling our thumbs. What a waste of time!!”

8. “When flying on the company plane, (facing seats), if her feet are cold, she just jams them up under the ass of the person across from her.”

9. “I once worked for a firm whose chief executive made promotion decisions based on graphology, astrology, and a variety of pseudo-scientific techniques. For instance, she would secretly acquire handwriting samples from new staff and decide on appropriate placement and position for each person based on the results. This activity was shared only with her direct reports. I learned all this to my horror when I was promoted into her staff (evidently I unknowingly passed the ‘tests’). I wanted to promote a very talented subordinate to a junior management position; a promotion she vehemently opposed on the grounds that an analysis of his handwriting and ‘aura’ had revealed him to be deceptive and deceitful.”

10. “He gave his employees used, counterfeit designer watches to reward them for their efforts.”


11. “Clips finger nails in meetings.”

12. “When a group of us were checking into a hotel for an out of town customer meeting, hitched up his pants and asked, young, female desk clerk: “Where can a man go to get some in this town?”

13. “One boss I had used to start meetings with, ‘I can’t sit down, I’ve just been ass-raped.’ In an ocean of inappropriateness, that one stands out!”

14. “I worked as nurse a few years back at a facility where the manager encouraged nurses to order extra valium when placing narcotic orders with the hospital pharmacy so staff ‘could have few for personal use.'”

15. “My boss ordered her best friend (also her subordinate) to collect money from the other subordinates to buy a $600 bracelet for her birthday.”

Finally, perhaps my favorite bosshole of all time apparently “water boarded” a subordinate at company picnic to increase motivation is his sales team. As the Washington Post reported in April of 2008:


No one really disputes that Chad Hudgens was waterboarded outside a Provo office park last May 29, right before lunch, by his boss.

There is also general agreement that Hudgens volunteered for the “team-building exercise,” that he lay on his back with his head downhill, and that co-workers knelt on either side of him, pinning the young sales rep down while their supervisor poured water from a gallon jug over his nose and mouth.

And it’s widely acknowledged that the supervisor, Joshua Christopherson, then told the assembled sales team, whose numbers had been lagging: “You saw how hard Chad fought for air right there. I want you to go back inside and fight that hard to make sales.”

Thank so much for sending in all those stories! I think it is time for a list of good bosses! These stories are fun in a sick kind of way, but it is important to remember that most bosses out there are doing a pretty good job and are aiming to get better.

Reprinted from Work Matters

Robert I. Sutton, PhD is Professor of Management Science and Engineering at Stanford. His latest book is Good Boss, Bad Boss: How to Be the Best…and Survive the Worst. His previous book is The New York Times bestseller The No Asshole Rule: Building a Civilized Workplace and Surviving One That Isn’t. Follow him at

About the author

Robert Sutton is Professor of Management Science and Engineering at Stanford and a Professor of Organizational Behavior, by courtesy, at the Stanford Graduate School of Business. Sutton studies innovation, leaders and bosses, evidence-based management, the links between knowledge and organizational action, and workplace civility