9 Things You Should Never Say to Your Boss

Tough love truth for a better life at work

Max Klein
7 min readMar 8, 2021
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I wasn’t thinking.

I was lamenting to my boss during a company meeting that “I need a challenge…I don’t feel like I’m working to my potential.”

Ooops.

Some great bosses may encourage this honesty but many others can see it as a problem. Mine was the latter.

There is also a time and a place for this conversation and a way to frame it in a career aspirations sort of way, but not in a whining to my boss off-the-cuff sort of way.

Sales is a profession with an open-ended definition of success so my statement conveyed two things to him. First, that I wasn’t challenging myself. And second, I needed someone else to challenge me to get my best work done.

So he did.

“How about you challenge yourself to sell more? I’ll come up with a goal for you next week” he said in an irked voice, and walked away.

There are just some things you shouldn’t say to your boss. Even if you do say them, they have to be said in the right setting or they aren’t received the intended way.

I’m not sitting on a high horse here — I’ve made all these mistakes myself. I write this to ensure you don’t do the same!

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