15 Things a Boss Should Never Ask an Employee

You’d expect inappropriate questions from your co-workers, but sometimes your boss can be the source of questions you’re not interested in answering. How do you know what’s appropriate and what’s not? We’ll tell you which questions to watch out for and why. Here are 15 things a boss should never ask an employee.

1. Do you want to see a photo of me in my workout clothes?

shirtless muscled man

Your boss should save the personal photos for friends and family. | iStock.com

The presence of smartphones with cameras has made everyone a photographer of sorts. Unfortunately, that sometimes means being shown pictures you’d rather not see. It’s OK if your boss wants to show you a few vacation photos. But things start to get weird when you’re shown pictures of your manager in various stages of undress.

It’s great your boss is proud of his or her physique, but there are limits when it comes to what is and isn’t appropriate to share at work. And it’s better if those photos of your manager in tight, sweaty workout clothes are reserved for friends and family.

2. Could you work through lunch?

man eating at desk

Are you expected to eat and work at the same time? | iStock.com

Your lunch time is your time to decompress and catch your breath. Your boss shouldn’t ask you to sacrifice your down time. In most cases, if your employer asks you to work during your lunch break, you must be paid for the time. Besides, working on an important project while you’re tired and hungry is a recipe for disaster. It can be hard to focus when all you can think about is a juicy cheeseburger and crispy french fries.

3. Could you check in with me during your vacation?

man in a suit on the beach

What’s the point of a vacation if you can’t truly unplug? | iStock.com

Some bosses take it one step further and make their presence known even when you’re trying to relax. They truly believe because you’re being paid for your services, you now belong to them. It doesn’t matter if you’re spending time with your family or you’re on your honeymoon. They expect you to be on call at all times.

If your supervisor insists that you check in and threatens to fire you if you don’t, see whether you can work out an alternative. Instead of checking in during your time off, Vicki Bowen Hewes, CEO of Dress for Success Columbus, recommends creating a form with updates you can give to your boss before you leave. This way, you won’t have to worry about responding to phone calls and emails while you’re relaxing on the beach.

Here’s what Hewes had to say on the Dress for Success blog:

If your group doesn’t already have one, create a one-page ‘Work in Progress’ (WiP). The WiP should include any projects you’re working on, their current status and next steps, any team members collaborating, and the projected completion date in an easy-to-read format. It’s also really helpful to include a list of vital contacts, too, including phone and email, that your boss or a team member can contact directly in your absence, should the need arise.

4. Can you cancel your vacation?

women strolling on a beach

You can forget that relaxing beach vacation. | iStock.com/jacoblund

Another question your boss might ask is whether you can cancel vacation plans you made weeks or even months in advance. In some cases, there might be a valid reason for rescheduling your vacation, such as if the company’s survival depended on it.

However, if the office wouldn’t collapse in your absence, this isn’t a reasonable request. Although an employer has the right to ask you to cancel, it puts you in a bit of a pickle if you’ve already booked your flight and hotel.

Unfortunately, human resources expert Alison Green said if your job depends on whether you cancel your plans, you’ll have to take cancelling into consideration. “I hope you won’t do this, but if you think [your boss] is unreasonable enough to jeopardize your job if you don’t, you’ll need to weigh that against everything else,” Green said on her blog, Ask a Manager.

5. I know you’re sick, but can you come in anyway?

Sick woman

Working when you’re sick isn’t a good idea. | iStock.com/samotrebizan

Working while you’re sick is like trying to push a truck uphill. No matter how much you try, you’re getting nowhere fast. Some bosses are super committed to the cause and will try to force you to come into the office no matter what shape you’re in.

If you’re just suffering from a minor ailment, such as a cold, your employer could press you about coming in. However, if you have a serious illness, you do have some rights when it comes to your ability to work.

6. Do you want to be friends on Facebook?

Facebook on smartphone

You might want to ignore that request. | Saed Khan/AFP/Getty Images

Facebook friend requests can be tricky. The risk in becoming friends on Facebook is there are likely private moments and photos that are best kept away from the eyes of work mates. Also, there have been too many cases of employees being fired for thoughtless comments left on a Facebook timeline.

Etiquette expert Steven Petrow wrote on his blog about an employee who vented his work frustrations on Facebook but forgot his boss was one of his Facebook friends. Things didn’t end well:

A friend of mine, who is president of a pretty big start-up, had become “friends” with a top manager in accounting. Then one day Mr. President read a status update from the employee that read: “I hate my [expletive] job. Can’t wait ‘til the weekend.” Alas, for the poor accountant, his weekend started sooner than anticipated — actually, the very next day, when he was fired.

Needless to say, it’s just better for both involved if that request is never sent.

7. Can you pick up my dry cleaning?

young female looking through a clothing closet

Just say no. | iStock.com/AVAVA

Can’t your boss hire someone to do this? Your supervisor might be too busy to pick up dry cleaning or perform other quick errands, but he or she shouldn’t expect you to do personal tasks. Unless you’re a personal assistant, it isn’t appropriate for your boss to ask you to run errands.

Politely decline, and suggest a local errand service. You can hire people to do everything — from laundry to dishes and even grocery shopping — these days.

8. Could you spy on our competitor?

manager sitting in cafe working on laptop

Ask why your boss is making this request. | iStock.com/Halfpoint

Some employers will go to major extremes to get a leg up on the competitor. They’ll even use their employees as a pawn in a ruthless corporate chess match. If your boss wants you to go to great lengths to get information on the competitor, you might want to reconsider staying at this job. Ask why this request is being made and what your boss wants you to do.

9. What’s your race?

woman smiling

You don’t have to share your ethnicity if you don’t feel comfortable. | iStock.com/Janet Rhodes

Depending on the circumstances, this question is rude. And the answer could be used against you if you’re not careful. Some employers still discriminate based on race or ethnicity, so this question should send up some red flags. During the employment process, however, employers are allowed to ask candidates to voluntarily share their race for affirmative-action purposes.

10. What are your family plans?

Pregnant woman holding belly

Your family plans are no one’s business. | iStock.com/tamaravidmar

No one needs to know how many children you plan to have or whether you’re planning on having kids at all. Although it shouldn’t happen, some supervisors ask about family plans as a way to decide who will stay or go in the event of a layoff. Some employers believe a worker with children will be less dedicated. If you’re ever asked this question, just say you’d prefer not to answer or that you haven’t given it much thought.

11. Can you babysit my kids?

baby pulling toilet paper

Nope. | iStock.com/markcarper

Let your boss know there’s something called a babysitter and that he or she should use one. A personal request of this nature shows a lack of concern for your time and a lack of respect for your job skills. This situation could present a potential conflict of interest, but it’s ultimately a personal decision.

A career expert at Marie Claire suggests if you’re going to babysit for the boss, at least ask to be compensated.

If you and the boss want to work out an arrangement where he pays you market rate for weekend/evening brat duty while he and the missus have a date night, that’s up to you. But Cubicle Coach thinks this goes beyond standard dues-paying scut. The next three times he asks, say you’ve got plans; if he’s not a monster, he should take the hint.

12. I know it’s illegal, but could you do this for me?

man putting money in jacket

See you in jail? | iStock.com

Don’t do anything illegal for your boss. If anything goes wrong — and it probably will — you’ll be the one to take the fall. Just don’t do it. You might also want to mention a request like this to your human resources representative. If he or she already knows about these illegal dealings and doesn’t see a problem with it, that’s a sign it’s time to dust off your resume.

13. Could you tell a (not so small) lie?

businessperson holding fingers crossed behind his back

Your boss shouldn’t ask you to tell significant lies. | iStock.com/stevanovicigor

We all lie from time to time, but some lies are much more serious than others. Your supervisor should not put you in a position where you’re being asked to tell a significant lie. A manager should be able to hold their own when faced with a tricky situation. Asking employees to lie shows a lack of character.

Stand by your values, and let your boss know you will not lie. If the lie gets uncovered and heads are on the chopping block, you’d better believe you’d be the first to go. Consider yourself thrown under the bus.

14. Do you want to go on a date?

young couple in the morning

If you want to get up close and personal, one of you will have to leave the company. | iStock.com/Ivanko_Brnjakovic

Is your boss putting the moves on you? If you’re in a situation where your supervisor is making unwanted advances, immediately let him or her know you’re not interested and would like to focus on work. However, if you are interested, one of you is probably going to have to leave the company — and it will most likely be you. Working with someone you’re dating can get hairy, so proceed with caution.

15. Could you do my work while I play golf?

man playing golf

Is your boss hanging out on the golf course while you work? | iStock.com

People ask their co-workers to cover for them all the time. Emergencies, illnesses, and child care issues happen, so it’s not uncommon. However, when the person asking is your boss and you have no idea how to do the job, that’s a problem.

If this happens to you, you’ll need to speak up. Let your boss know you are not comfortable with the request. Trying to do a job you weren’t trained to do could lead to big mistakes that could get you fired. Express your concerns now before it’s too late.  

Follow Sheiresa on Twitter @SheiresaNgo.

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