Weird Demands from Bosses

At one of my previous jobs, we had a new CEO come aboard. He was rather personable and came around to speak with everyone. When he came by to my desk, it was like we were old friends just talking it up. I was very much in a junior position then and it felt good to just have a chat with the big boss.

When he left, my direct supervisor, a manager, came up to me and asked me to continue the “relationship” I had with him. It was an odd request for me; what was I supposed to do? Ask the CEO out for drinks or maybe I could go out for a game of golf with him? When pressed further, my manager admitted that my purpose was to spy on him; see if I could get the “goods on him”.

Well, obviously that didn’t work out well. What was a young fella (about 18 years his junior) and holding a junior position supposed to do to “connect” with someone like that? Beats me.

Weird requests from bosses seem to be a commonplace. I had another boss ask for a loan to pay off another loan (very dubious that I will get the money back; it is not like I could pester him for it. I might get a bad review or lose my job). You too, would probably have your own tales to tell. Ask around your friends and you will hear stories of their own.

Earlier this year, Jobs website CareerBuilder compiled a list of the strangest things bosses have asked their workers to do. Here is a list of 15 real-life examples of this strange behaviour (seems like No. 3 happened to me):

  1. Boss asked employee to be prepared to delete all emails and computer files at a moment’s notice.
  2. Boss asked employee to be a surrogate mother for her—more than once.
  3. Boss asked employee to spy on senior management.
  4. Boss asked employee to buy a rifle for him, and he would reimburse the employee.
  5. Boss asked employee if she knew of anyone who could “hook him up” with illegal substances.
  6. Boss asked employee to go online and post false good comments about him.
  7. Boss asked employee to come up with a science fair project for her daughter.
  8. Boss asked employee to fire the boss’s brother.
  9. Boss asked employee to lend him $400 for a down payment on a car.
  10. Boss asked employee to remove her stitches.
  11. Boss asked employee to be better friends with him.
  12. Boss asked employee to scour an abandoned office building for furniture and supplies they could use.
  13. Boss asked employee to bail another coworker out of jail.
  14. Boss asked employee to clip her dog’s nails.
  15. Boss asked employee to help plan her wedding.

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