7 Things to Never Say to Your Boss

Has the relationship between you and your boss become chummy? Has it developed into a friendship outside work?

When your colleague becomes your friend, the line between professional and personal behavior can easily be blurred, putting the relationship and business decisions at risk. This is especially true in the dynamic between boss and employee. For this reason, there are definitely things as an employee (and friend) you should never say to your boss.

Do Not Cross the Boss-Employee Line

Many companies address the boundaries between boss and employee relationships in their policies and procedures manual. The wrong perception or questionable behavior can challenge the ethics and legality of this relationship.

things to never say to your boss

Some of the concerns are:  

  • Will the boss show favoritism?
  • Is this employee privy to confidential information?
  • Do other staff members feel restricted from expressing concerns about this ‘favored’ coworker?

Use Common Sense When Talking to Your Boss

As a subordinate, you may want to think carefully about how you speak to your boss, how often you hang out in their office, and whether you unknowingly flaunt your relationship.

Is your friendship with your boss putting both your #careers at risk? Maybe it’s time to draw some #professional boundaries. Click To Tweet

An easy way to ensure that you are maintaining a professional and impartial relationship is to keep in mind these two ideas:

  1. Practice common sense when you interact with your boss at work: Think twice about talking about your personal life. Rebuild bridges with neglected coworkers, perhaps inviting them to lunch. If your boss is talking to a coworker, don’t butt-in.
  2. Practice reasoning (a great soft skill to hone): If a coworker shares something personal with you like she’s looking for a job, don’t run and tell your boss. If your boss asks a coworker to attend a conference (not you), accept the decision and congratulate your colleague. Don’t use your relationship with your boss to try to change things in your favor.

If your friendship with your boss is genuine, you’ll do what’s in the best interest for both of you. A friend does not put a friend in awkward situations, nor do they take advantage of the relationship.

When you’re at work, maintain a professional relationship with your boss—treat each other according to your positions. That means keeping your comments neutral and respectful.

Things You Should Say to Your Boss

Of course, if you don’t have an especially friendly relationship with your boss, you could be faced with another problem. You might fear contact with them and not know what to say if, for example, you are trapped together in an elevator.

This article from Business Insider  (“Here’s Exactly What to Say When You’re Stuck in the Elevator With Your CEO”) can provide you some guidance. Key to the advice here is just conducting yourself like a normal human being with your boss, rather than fleeing the elevator early or staring stonily, and silently, ahead.

If you haven’t formally met before, introduce yourself with a handshake and direct eye contact. Bring up something happening in the company, or thank the boss if they have done something good for employees, or ask about how their vacation was, if you know they’ve recently been away . . .  You get the idea.

If your boss is distracted or curt with their replies, then take the hint and enjoy the ride in silence.

Here Are 7 Things You Should Never Say to Your Boss

OK, if you read the list below and don’t cringe for some of these verbal missteps, then you need to ask yourself if it isn’t time to put up some barriers between you and your boss. Do some soul searching if you could see yourself saying:

things to never say to your boss

  1. Have you seen that hottie on the second floor?
  2. Hey, if you need something done today, call Gisselle. I’m still feeling hungover from last night.
  3. I blew my money on [fill in blank]. Can you front me until payday?
  4. I’m leaving early today. If anyone asks, tell them that I’m doing some research for you.
  5. I’m taking one of the company laptops (a pack of coffee, a case of waters, etc.) home this weekend.
  6. Jorge told me he’s looking for another job.
  7. I can get everyone to do whatever I say. They know we’re friends.

If you say any of these things, you will put your boss and friendship in a compromising position. The person in charge must consider their duty in upholding the company’s policies equitably. Expecting special treatment or asking your boss to overlook an infraction may cost both of you your jobs.

Maintain a Professional Relationship with Your Boss

You should strive to maintain a business-like relationship with your boss, especially during working hours.

things to never say to your boss

Don’t say the things you should never say to your boss. This will strengthen your professional reputation with boss and coworkers alike. It will diminish the perception that you are receiving special treatment, so your coworkers will be more inclined to trust you and socialize with you. And it’ll help your boss maintain morale, command structure and staff respect.


Rosalinda Oropeza Randall, Workplace Civility, Soft Skills, Business Etiquette Expert, Media Source, and author of “Don’t Burp in the Boardroom.

Presentations are available to support HR policies and harassment compliance, address specific concerns –  upgrade or set a standard of communication and behavior  –  training for new managers – interns – new-hire orientation process –  professional development training –  events or conferences – college/university students  –  athletes on public behavior  –  actors to prepare for roles  –  Attorneys; polish client’s professional presence for a court appearance.

For more information, please contact me via email, or by calling 650.871.6200 before a dilemma turns into front page news.

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