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36 things you should never say to your boss

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While honest communication is crucial between you and your boss, some things are better left unsaid.

Individuals speaking at work.
There are certain phrases you should never say to your boss in the office. Photo: Klaus Vedfelt/Getty Images

By Jacquelyn Smith , Marissa Perino , and Rachel Gillett

Getting along with your boss can be great, especially when it makes the daily grind that much more enjoyable.

You may even feel so close to your boss that you hang out after work or invite them to your wedding. But at the end of the day, it’s important to remember that your friend is still your superior, and there’s a line you probably shouldn’t cross. Honesty is the best policy in the workplace — but like any rule, this one has a few exceptions.

“It’s important to be cautious with what you say to your boss, as even the slightest slip up could make or break your career,” said Ryan Kahn, a career coach, founder of The Hired Group, and author of “Hired! The Guide for the Recent Grad.”

We talked to several workplace experts to gain their insight on what they consider phrases that you should never say to your boss, even if you are friends. Responses ranged from simple questions such as “Can I be honest?” (which implies you are not always truthful) to how you ask for vacation days.

Aside from the obvious — like profanity and insults — here are some words and phrases you should never utter to…

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Responses (23)