6 Things You Shouldn’t Say to Your Boss

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We’ve all had our run ins with our employers that have caused us problems at work. Sometimes they’re our own fault and sometimes they’re things we can’t control. Most of the problems I’ve had with an employer were self induced.

This is a list of things that you shouldn’t say to your boss unless you’re looking for trouble. These of course are all hypothetical situations and are not in any way based on real life events.

1. Is this your house key? – I had to go by my boss’ house when running a business errand in his truck. When he handed me the keys I asked which one was his house key. He promptly took them back and removed the house key. Anytime after that he would make sure to give me the set of keys without his house key.

2. I should write this down – On a previous blog I had written some more detailed posts about my work and what went on there. My boss (and biggest fan I assume) decided that he should discuss these things with me and “encourage” me to stop writing about work. I asked him to hold on a minute so I could get a pen, “I should write this down, this would be gold for my blog” I said when I got back.

3. The only job left for me is yours – During a performance review when I had been with the company about a year I was asked if I wanted to keep moving up in the company. Straight faced I responded “The only job left for me to takeover is yours”. The stunned look on his face was priceless.

4. Yes, I did sleep here last night – I was having an issue with tardiness, so in an effort to show that I was serious about getting to work on time, I got to work before everyone else and setup a sleeping bag in my office and even put a video of a fireplace on my computer screens.

5. Can you see from your kitchen? – When leaving to go home for lunch one sunny day, he asked if I could see if a customer came in from where I was. I was sitting behind the building at our picnic table, on my unpaid lunch break. My answer was “No, can you see a customer come in from your kitchen?” We had a chat about that one later.

6. Here’s the deposit book – Our normal routine was for me to fill out the bank deposit book and my boss would take it to the bank on his way home for lunch. One slow winter morning there was nothing to deposit, so I put a sticky note that said “Sucka! No deposit today” in the book instead and sent him to the bank as normal. After he waited in line for 20 minutes, he got to the window and opened the book for the teller (who was one of my friends) to find nothing but a sticky note.

Somehow through all of these I managed to not get fired. I think maybe in the future I should do a post on how to get out of trouble at work.

What else should you not say to your boss?


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