how to ask your boss these awkward questions

No matter how awesome and understanding your boss is, some questions are still super hard to ask. Even the best boss in the world can make you nervous when you have to ask them something awkward. Here are some of those questions — and the best way to approach them.

  1. Why Did I Get Passed Up for That Promotion?

Getting passed over on a promotion is one of the worst feelings in the world, especially when you think you’ve earned it. It’s extra difficult to deal with when you’re obsessing over why you weren’t the one who got it. It’s reality that women get passed over for promotions even when they have the same qualifications as men. However, you can’t just come out and ask that’s the reason.

Phrasing is essential when you ask this question. Saying, “Hey, why did Tom get that promotion and not me?” isn’t going to do you any favors. It makes the question confrontational and demanding, and also makes you seem whiny.

Instead, ask them what you can do to get you to that next level. Focus on seeing how you can take steps to make yourself a better worker instead of being accusatory. Bosses like to see their workers taking initiative and wanting to improve, so they’ll definitely take notice.

  1. Why Haven’t I Gotten That Raise I Was Promised?

This is another one that can sound demanding if it’s said the wrong way. Don’t assume that it’s your boss’ fault that this hasn’t happened. It’s excusable if things have gotten busy and it isn’t their priority.

If you ask this, it’s also an invitation for critique on your work ethic and what you’ve been doing for the company. Maybe you were told there might be a raise when you switched to this new department, but your work hasn’t been living up to their expectations.

When you ask, make sure you focus on your tone and wording. This is never a fun thing to bring up, but make sure you keep things neutral. Focus again on what you can do to make this happen. Ask if there’s something you could be doing differently or something extra you can do to get this raise.

  1. Since Everyone Else Has Been Doing It, Could I Work From Home or Telecommute More Often?

Using a phrase like “everyone else is doing it” instantly makes you seem like you’re complaining and want them to feel bad for you. Focus on yourself instead of other people at the company. How they get their work done doesn’t matter.

Do some research and highlight all the benefits of telecommuting to your boss, like the 13 percent increase in productivity. If you show that you know your stuff and that this could definitely be a good thing for both you and the company, your boss is more likely to bite. They’ll hopefully at least give you a trial period to see if the telecommuting works.

  1. Can I Get an Increase in My Salary?

According to a survey, 57 percent of people haven’t asked for a raise. Yet almost half of satisfied employees who asked got the exact raise they wanted. Before you approach your boss about this, do research to see what other people in your position are making and see what a reasonable pay rate would be for your raise.

Make sure you also gather evidence to back up why you think you deserve the raise. Highlight any extra certifications you’ve received since you got the job or at your last promotion or pay increase. Note any extra responsibilities you’ve taken on, projects you’ve led, positive customer feedback you’ve gotten — anything that can prove your worth to the company.

Plan out the conversation you plan to have with your boss and make sure you avoid letting emotions cloud your argument. Planning it out before can help keep you calmer when the confrontation actually happens and gives you a chance to choose appropriate wording.

  1. Are You Joking or Being Serious?

When you’re a new hire or you just got a different boss, it can be hard to feel them out at first. Are they a jokester or someone who’s deadly serious all of the time? 91 percent of executives think a sense of humor is important for career advancement — but what if they’re in the other 9 percent?

If you think they’re making a joke about your duties at work, say something like, “Well, since we’re still getting to know each other, I just want to make sure that’s something you definitely want me to do.” This way you could play off getting the joke, as well as still making sure you’re fulfilling your tasks.

  1. How Do I Do This?

Problem solving is a skill every boss wants an employee to have. Your boss wants you to be able to learn and figure things out for yourself, but sometimes you just might get stumped. Don’t bluntly come out and say something like this, though.

Make sure it’s something that you really need help with and not something you’ll be able to figure out five minutes later when you actually give it some thought. When you ask, say that you aren’t sure exactly how to proceed and provide some solutions that you think might do the trick to show that you aren’t giving up before you’ve even tried.

  1. Is This Meeting Ever Going to End?

You don’t want to criticize your boss on his ability to keep meetings concise or interesting. You also don’t want to make it look like you aren’t a team player or that you aren’t engaged in the topic of the meeting.

Try to focus on the positives of ending the meeting on time. Everyone has a lot of work on their plate, so emphasize the benefits of ending on time and making sure everyone stays up to date on their workload.

  1. How Can I Get the Same Treatment as My Coworker?

Bosses pick favorites. It just happens. But maybe if you aren’t getting the same treatment as the coworker a few cubicles down, it’s because of your work performance.

To start, take a look at what that coworker is doing compared to you, if you can. Are they going above and beyond to take on extra duties? That could be why they’re a shoe-in for the nice corner office.

If you confront your boss, focus on how you can bring your work level up to whatever your coworker’s is. Ask if there’s something you can do to get more recognition in the company so you can get the same benefits that your coworker is getting.

  1. What Strengths Do I Have That Will Help Me in My Career?

This question can feel like you’re fishing for compliments, which no one likes to do. It also helps you show your boss that you want to take control of your career and be the best you can. Your idea of what your strengths are could be totally different from your boss’ ideas.

Phrase it so it looks like you’re curious and interested on how you can emphasize those strengths to be the best employee for the company. Everyone is so focused on weaknesses, that this could also make your boss take notice because you’re asking something different.

  1. What Am I Supposed to Be Doing?

You don’t want your boss to think that you don’t have any idea what’s going on. Still, sometimes bosses get busy and don’t give clear instructions as to what everyone’s roles and goals are for the day or project.

You don’t want to let this go and do something that’s assigned to someone else. Plus, if you don’t know any goals, you won’t be able to exceed expectations or have a shot at a promotion.

Simply ask your boss for clear goals for the current project because you want to make sure things are done perfectly. If they don’t give you an answer, make a list on your own and show them. This demonstrates initiative while also getting you the answers you need.

  1. Can I Have a Layoff?

If you really dislike your job and are unhappy, you can ask your boss for a layoff. They’ll most likely be more than willing to give it to you in order to find someone else that’s willing to do the job. If you know layoffs are coming up and you volunteer, you could save someone else’s job.

Make sure you leave the company on good terms. Don’t come out and say that you hate your job and/or your boss. Tell them that you’ve really enjoyed working for the company, but due to various reasons, you would want to be considered for a layoff if one was going to happen.

Have you ever asked your boss any of these tough questions? How did it go? Share your experience in the comments — and share this article to help out all the professionals in your life. While you’re here, be sure to subscribe to the PC newsletter for all the latest news and tips!

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Sarah Landrum is the founder of Punched Clocks.

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