Questions not to ask your boss sometimes just slip out. We’ve all done it — opened our mouths before our brains engaged and asked our boss a question that undermined our career (or could have). Like the time I asked my boss what motivated him (do you think that’s not a bad question, wait until you see where I took it). His answer was “money”. Of course, he asked what motivated me, and I said, wait for it — not money.

“Money doesn’t motivate me! I’m motivated by recognition!”

He asked me, “Why in the HELL am I paying you bonuses?” I quickly said, “Ah — a-a-ah to, to, to, a-a-a… recognize me?

He recognized an opportunity to help the bottom line, and I was taken off of all bonuses for a year. I’m not making this up.

The Top Ten Questions Not to Ask Your Boss 

10. I’m thinking about a second job; can I use you as a reference?

9. Can you help me with my garden on Facebook?

8. Have you gained weight?

7. How did someone like you become boss?

6. Was that you at the game yesterday when I called in sick?

5. Can we talk politics?

4. So, what do you do around here?

3. Does anyone time our lunch breaks?

2. Is it true people can’t smell vodka on your breath?

And the number question not to ask your boss is…

  1. Do you care if I leave early? I have an interview.

Bonus questions not to ask the boss

  • Are you pregnant?
  • What’s your best remedy for a hangover?
  • Is it okay to have a few drinks at lunch?
  • Is it alright if I catch up on Game of Thrones while I work?
  • I’m out of vacation days so how do I take sick days if I’m not sick?

I know there are great stories out there — so share them with me, please. What’s the worst conversation you ever had with a boss? Or the silliest question you were asked as the boss.

I like to have fun here, but I can be serious too. So, how can I help you?

How Can I Help You?

I like to help people and organizations, but I have three criteria I consider before taking an assignment – I believe in what the organization stands for, I know I can help, and it looks like fun. If you have any questions, Contact Me. 

So, does your business have a management training plan? Because, if not, many organizations, large and small, use my book, The New Manager’s Workbook a crash course in effective management, as the basis for their leadership development program. Check it out. It might help you stop putting off what you want to do.

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