12 Questions You Should Never Ask Your Boss

There are certain topics that shouldn’t be discussed — especially when talking to management — if you’re hoping to advance.
Last updated Nov. 28, 2022 | By Laura Gesualdi-Gilmore | Edited By Jacqueline Burt Cote
angry businessman shouting to an employee

We may receive compensation from the products and services mentioned in this story, but the opinions are the author's own. Compensation may impact where offers appear. We have not included all available products or offers. Learn more about how we make money and our editorial policies.

No matter the workplace, there are certain boundaries that shouldn’t be crossed when talking to superiors.

Even if you have a close relationship with your boss and think of them as an equal in the workplace — or even a friend — there are certain questions that simply should not be discussed.

That is especially true if you’re hoping to advance at your company and move beyond living paycheck to paycheck, or if you plan to ask for a raise in the near future.

Here are 12 things you should never ask your boss at work.

Is this part of my job description?

fizkes/Adobe businessman listening to young male employee

Whenever you take on a job, expect that the job description will not be set in stone. Priorities change, and while it’s fine to set boundaries at work, you also want to avoid appearing inflexible and unwilling to adjust to company needs.

Career experts often say that being willing to step outside of a role at times demonstrates a dedication to the company’s success. Plus, learning new skills makes you more of an asset to the company.

Can I leave early for an interview?

Production Perig/Adobe attractive woman being late to a rendezvous

No matter your reason for looking for a new job, it’s probably in poor taste to advertise it to your boss. Employees should avoid asking to leave early or otherwise skimping on current work responsibilities while interviewing for other jobs.

If you want to interview for a new job, it may be best to take paid time off or schedule the meeting outside of your current work hours.

Do I have to work with that colleague?

insta_photos/Adobe business team developing business strategy

In a professional environment, you should be able to get along well enough with others to get work done. Even if a colleague is not your favorite person, avoid complaining about them to your boss or asking for accommodations that may make your supervisor’s life harder.

If there is a serious issue with another employee — one worthy of bringing it to the attention of human resources — that is a different story. But avoid asking for preferential treatment simply because you don’t like working with someone.

Can you cover lunch?

Nusara/Adobe employee was complained by boss

In many workplaces, management likes to treat the staff. Perhaps your boss occasionally pays for lunch or after-work drinks, or buys cakes to celebrate employee birthdays.

However, employees should not expect this type of generosity regularly.

Even if you forget to bring cash for lunch one day, think twice about asking a boss or a colleague for a few dollars. In many cases, expecting someone else to cover your food needs is crossing a workplace line.

Can you (or a colleague) handle that instead?

xreflex/Adobe boss complains to businesswoman employee for mistake on her job

Regardless of your relationship with your boss, constantly asking them to pawn off work on other people is not a good look. This resistance to taking on responsibility — or taking on tasks you’re not particularly interested in — is unlikely to go down well with your supervisor.

Management will likely remember such lack of enthusiasm when it comes time to think about promotions or raises.

Can you get rid of my colleague?

fizkes/Adobe tired businessman with painted eyes on stickers

If your boss hasn’t asked for your opinion specifically and you are not involved in the hiring and firing process, it’s best to keep your opinion about who should get the ax to yourself.

Career experts also advise against engaging in workplace gossip in general. Let management take care of who they want to keep on staff. If you’ve noticed a colleague’s performance lacking, it’s likely that your boss has, too — so there is no need to pile on.

Can I leave early when things are slow?

Sathaporn/Adobe boss looking down at lazy colleagues sleeping on table

If you must leave early for an event or an appointment, it’s fine to request this, as long as it’s not an everyday thing. However, employees should avoid asking if they can leave just because it feels like a slow day.

No boss wants to hear that an employee who is being paid is sitting around doing nothing — especially since there is likely something you could be doing.

A more impressive question would be, “What can I get involved in if I finish all the work on my plate today?”

Can we put that task off?

Syda Productions/Adobe businessman with smartphone at office

In many workplaces, priorities change from day to day, and even throughout the day. If your boss comes to you with a new task while you’re still in the process of working on another, there are better options than asking, “Can I do that later?”

Instead, ask your boss which task is the top priority.

Can I take home coffee or toilet paper from the office?

bnenin/Adobe colleagues having a coffee break

Even if your office seems lax, it’s a good idea to avoid stealing supplies from it — and roping your boss into the process. Believe it or not, stealing from the office can be considered a fireable offense, or even a crime, in some offices.

So, don’t ask your boss for the OK to nab a box of coffee or a few rolls of toilet paper.

Are you pregnant?

fizkes/Adobe female mentor instructs an intern

Unless the boss has shared that they are expecting with you, don’t ask about a suspected pregnancy. In fact, you should never ask this question, whether you are talking to your boss or someone else.

Whatever the answer is, the situation becomes awkward once the question has been asked. Either they are not pregnant and will be offended, or they are expecting and have chosen not to disclose it yet. Either way, it’s best to wait to be told about a pregnancy.

What’s going on with you lately?

pressmaster/Adobe business people discussing work project

It’s important to consider workplace boundaries even with those you feel close to. If you have noticed your boss acting a bit off lately, there are more polite ways to go about asking if they are OK than blurting out, “What's been going on with you?”

Better, more professional options — “Just checking in to see if you’re OK” or “I’m here if you ever want to talk” — would be a better move in this situation. It’s also important to consider that everyone, even your boss, has bad days. Sometimes, it’s better not to raise any questions.

When will you retire?

Blue Planet Studio/Adobe senior engineer wearing a hardhat and safety vest

Not everyone wants to talk about their age or their life plans with employees. What’s more, retiring can be a touchy subject for some people.

Career experts warn against broaching this topic, which is simply none of your business. Instead, focus on your own golden years by directing your energies to working hard and saving enough to retire early.

Bottom line

Elnur/Adobe angry boss shouting at his employee

Even with the friendliest of bosses, there is an air of professionalism you should maintain in the workplace. Avoid anything that may lead to an uncomfortable conversation or make your boss question whether you’re really dedicated to the job.

A professional and responsible attitude is something managers remember when it’s time to give out raises or promotions.

However, if you are working at a job where a raise seems unlikely for the moment, remember that you can take steps to make more money — like picking up overtime or considering a side hustle — that will put you in a better financial situation.

Get Paid to Go Shopping Learn More
Earn Cash Taking Surveys Learn More
Build Credit with Everyday Purchases and Regular, on-Time Payments Learn More

Author Details

Laura Gesualdi-Gilmore Laura Gesualdi-Gilmore is a seasoned freelance writer who also teaches writing courses at Rutgers University. She's based in Jersey City and enjoys travel, live music and, of course, spending quality time with her pup.