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How to Ask Your Boss a Touchy Question

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Summary: If you need to ask your boss a question on a touchy topic, you should follow the advice outlined in this post to be successful.

People do not like uncomfortable situations and they can be very difficult for them to avoid, especially when at work. At one point or another during your career, one of these situations will arise. More than likely, you will need to ask your boss a question on a touchy topic. You need to know the best way to ask these questions so you do not create an awkward situation or put yourself at a disadvantage in the office. We will discuss the best ways to broach difficult subjects with common workplace scenarios in this post.

Requesting an Increase in Salary

Asking for more money is never a fun thing to do, especially when you have to ask your boss. Before you even consider asking for more money, you need to do a little research first. You must find out what employees in the same position are making at other companies. This will help you present your case for a salary increase.

Once you have the salary information you need to put together a list of extra responsibilities you have conquered at the office and any achievements you have reached. When you have all of this ready, schedule a meeting. Outline what you have done in the past year, how you have consistently met deadlines, performed well above what has been asked of you, and that you would like to have your salary match your performance.

Missing Out on a Promotion

Another difficult topic to discuss with your boss is why you were passed over for a promotion. If you honestly do not understand why you were passed over for a promotion, you need to discuss it with your supervisor and not stew over it. Never ask about the situation in a confrontational manner. Instead, let your boss know how interested you are in advancing within the company and then ask what it is you can do better in your current position.

Ability to Telecommute

Does your company offer some of its employees the opportunity to telecommute one or more days per week? If so, and you have not been offered yet, this is something you can ask your boss about when the time is right. Never make this question about those in the office who telecommute. Instead, talk about how you can make this happen for your situation. Ask your boss if a trial period is possible so the company can see how well you will perform working from home.

Promised Raise Has Not Happened

Were you promised a raise recently? Has it yet to be reflected in your paycheck? No one wants to ask about a missing raise, but if you were promised one, you need to find out what has gone wrong. Never enter the conversation with a negative attitude. Instead, speak with your boss about the promise that was made and what you need to do to make sure it occurs. Do not blame your boss, or even the company, for failing to recognize your raise. This will get you nowhere.

How to Ask Your Boss a Touchy Question by
Authored by: Jim Vassallo