How to ask your boss tricky questions in the workplace

It is hard to find someone who enjoys awkward workplace situations, and often times those awkward moments make it hard for many to stand up for themselves and ask for what they may deserve or need. Taking the initiative and asking important questions can make you look confident, professional and can help you earn the respect of many.

In this article, we will examine some potential options for answering some of the workplaces most tricky questions.

Asking for promotions or position changes

When looking to get promoted within a company, sometimes it might feel nerve wrecking. When going to ask your boss, you want to make sure that you don’t come across hypocritical and say something like, “I was just thinking I should get promoted because I am the only one capable of doing this specific job”

Instead, don’t lay out why you are the only candidate for the job or promotion, but why YOU would be a GREAT candidate for the job or promotion. You could say something like, “Would we be able to sit down and chat sometime about how I would be able to reach the next level?”

Something simple like this hopefully will get you in on a conversation with your boss where you can discuss it with him or her. Then, you can lay out your case, on why you are a good worker, have the capable skills for the job or position up for discussion, and how if you were able to take this hypothetical role, how it would benefit the organization.

Asking about a raise

Do you feel like you are being underpaid for the work you are doing or the time and effort you are putting in for your company? Hopefully, the approach below will help you achieve a higher wage. Remember, you will have to convince your boss that the amount of money you are asking for is worth it due to the work you are contributing already, not JUST the work you are going to contribute in the future.

A better approach: “Over the past 12 months, I have always consistently been on time, exceeding the expectations you have given me (feel free to insert examples of you exceeding expectations here) as well as helped Chris and coached him through another project. I was wondering if there would be any possibility given this to get a raise since I have been so consistent with my work and trying to go above and beyond when possible.”

This is obviously a long-winded solution, but it is something you can take bits and pieces of and apply to your own situation. Coming at it with this approach, where you lay out why you feel like you have proven yourself will hopefully help your case, rather than attacking your boss on why you need a raise. There are many times when the person you work under is managing many people, and it may be hard for them to always remember every overachieving moment you have and why you deserve a raise, so this is a nice subtle way to let your boss in on the idea you believe you deserve a raise.

Asking for a day off

Not sure how to get a day off? Just walking in and asking “Can I have Friday off? I am going out of town” may not quite work that well. If you’re not sure how to ask that in email form, or any other tricky question like that, remember the following: Ask as early as possible, lay out your request in detail, and try to work around the business’s schedule

Let’s use a hypothetical on your manager named Jason. You want to ask for a day off on July 2nd because you have plans to see family for a long weekend over the 4th of July. Think of ways you can compromise with your boss, where even though he may lose you at the job for a day, let’s say you try to get things done ahead of time. Here is an example you could use:

Hey Jason, I wanted to reach out to see if I would be able to get the 2nd of July off to travel and see family. I know we have an important project that week, but I already have gotten a jump start on it and plan to have it done the day before so you’re not waiting on me. Let me know if something like this would be possible, thanks!”

Examples like these hopefully will help you speak up for yourself, it is something that may seem very daunting at first, especially in a workplace setting. With that said, if you can, you may be able to change many work situations, get promotions or raises, as well as learn different public speaking skills. These are all things that will come from speaking up, so you will not regret it!

By Jon Spahn
Jon Spahn Career Mentor