9 Things You Should Never Say to Your Boss

Tough love truth for a better life at work

Mix and Match Studio on Shutterstock

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.”


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!

#1. “I Need a Raise”

You already negotiated your salary. Or you accepted an advertised one.

If you bring to your boss “I need a raise because….” it comes off that you are a poor financial planner. If you can’t handle money at home, how will you at work?

Especially if the reason is “…my kids need shoes” or “…my bills are adding up.”

It’s harsh, but your boss doesn’t represent a charity. They represent a business whose goal is to minimize costs, including your labor.

Don’t ever bring personal reasons into a justification for why you need a raise.

Instead, at the appropriate time, sell why you deserve a raise. Or how you’ve earned one. Show how you are bringing more money into the company or otherwise adding value.

Justify why you’re worth more to your company, not why your company should be worth more to you.

#2. “ Bla, Bla, Bla (BS)”

It is exponentially better to say “I don’t know, but I’ll find out” when asked a question you don’t know the answer to during important conversations.

This applies to customers, your boss, or anyone.

When you respond with a lot of talk but little substance, it irritates people. They know they can’t get a clear and accurate answer from you.

BS isn’t a bad thing in less critical conversations though. You don’t have to stop doing it. Just choose when to do it.

It’s especially important to not BS when the truthfulness and accuracy of your answer are crucial.

#3. “But, We’ve Always Done It This Way!” or “At My Last Job…”

You may think saying “we’ve always done it this way” shows adherence to tradition or how things worked to make the company what it is, but mostly it’s just viewed as a shortcut to thinking — a lack of ability to adapt.

Things change. Doing something simply because you’ve always done it isn’t a virtue.

Secondly, don’t say “at my last job.” No one cares about your last job, especially your boss. Unless you worked for a direct competitor and they can glean some intel from that, they don’t care.

That’s like saying, “They did it better at the company I just chose to leave for this less-good company of yours.”

None of that is what you meant, but it’s how it’s taken.

#4. “I Need a Challenge”

As stated above, don’t say this unless you have a great boss who welcomes this honesty.

Great bosses value your input like this, while not-so-great bosses handle it in a way that hurts you more than helps you.

For many bosses I have had this is like saying “I have no initiative or drive, so please micromanage me.”

So just be careful who you say this to.

Challenge yourself if your boss doesnt want to hear it.

Employees who don’t challenge themselves under average or below average bosses end up micromanaged.

#5. “That’s Not In My Job Description”

Job descriptions are rough outlines of duties — they aren’t promises of the limit of activity you will be asked to do.

The statement “that’s not in my job description” immediately labels you as a trouble-maker. A challenge. A less-valuable and limited-capability employee.

You can say this of course if your boss is asking you to do something that unfair due to a sexist or racist attitude. But if they’re just asking you to do something outside the norm then go for it!

A “can-do” attitude in employees is most prized by leaders.

Even if what they’re asking you to do is out of the norm, roll with it. Excel at it. These times are an opportunity to show your versatility, adaptability, and can-do attitude that make a boss see you as more valuable.

#6. “ I Feel Like….”

Drop the “I feel like” and just say what you want to say. Same with “I don’t know but…”

You are immediately disqualifying what you are about to say when you say these things first. These types of statements plant doubt in people’s heads.

Now, if you truly are talking about feelings such as in marketing or having a brainstorming session for creative design or something that requires non-committed statement, it’s fine to say this. But don’t pre-qualify every statement you make with disqualifiers as a daily habit or people will learn to not value as much what you say after it.

The same way with ending non-questions in a questioning way to sound non-committal.

Saying “I feel like maybe we should look at a new approach to customer service?” with a question-sounding ending means everyone is thinking “whatever he just said, they don’t even believe it, so why should I?”

That idea of yours is only taken with the grain of salt that you yourself provided.

To have your words respected, don’t disqualify them before you say them or weaken them with question marks if they aren’t questions.

#7. “That’s Not My Fault”

Sometimes it isn’t your fault, but saying that makes it sound like your quick to shirk responsibility.

Instead, start offering solutions or fixes or how it could be handled now and in the future.

If you truly did mess up, admit it 100% and learn from it. Good leaders appreciate people who take full responsibility.

Only as a last-ditch effort to save your job and only if it’s true should you use “it’s not my fault.”

#8. “That’s Impossible”

Even if you think that’s the case, the statement implies you lack creative-problem solving abilities, self-confidence, and optimism.

It subliminally labels you as a non-creative inside-the-box thinker — a doubting and insecure employee.

Instead, you could say “this will be quite a challenge” or “we can give it our best effort” or “sounds nearly impossible, but anything is possible.”

The only way you even have a chance to succeed is when you believe you can anyway, so why fail before you even get started with a statement like this?

#9. “That’s Not Fair”

Nothing is fair in life. That statement comes off as someone who just left grade school or hasn’t reached adulthood.

It comes off as not being grounded in the reality of self-sufficient “adulting.”

Nothing is fair, ever, anywhere — but especially in business.

That being said, if they are treating you unfairly because you are a woman or person of color or some other truly unfair reason, then by all means should you say “that’s not fair… and here is why!”

Generally the statement “that’s not fair” though shows a lack of maturity and experience and plants a seed in a boss’s mind that they’ll be stuck holding your hand on your journey into adulthood.


I’ve made all these mistakes.

Most of these statements didn’t get me fired, but they also didn’t pave the way for my success.

A few of these statements even led to self-imposed micromanagement, doubt, and being relegated in management’s mind to just a place filler.

On the other hand, when I avoided these statements altogether and projected a can-do, truthful, responsible, positive, creative, mature vibe instead, my stock went way up as did professional opportunities.

And you know, I feel like, and I don’t know, but you may think because you’ve always done it this way that none of this really seems fair?

Yes! It isn’t fair.

It’s the truth!

It’s also the truth that when you don’t say these things work becomes a much better place to be.

**Edit 3/19/21: I’ve gotten a few responses regarding just being honest in SOME of the points above. I totally agree. With a great boss, verbal honesty IS valued. Honesty, in general, should always be priority. But there’s a huge leadership deficit out there. 76% of people with their resume on Monster say their boss is toxic. With an average to below average boss (which most of us have), it’s just better not to say certain things sometimes because saying them can make YOUR work life worse…not because of you, but because of them. Some of these points don’t apply to great bosses. I thank you all for the feedback and engagement!

Family Man. Leader. 3x Top Writer. MBA Strategy and Management. Marine Corps Veteran. Winemaker. emaxklein@icloud.com

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store