How to ask your boss for a raise or day off, and other tricky questions

Maybe it's your grandma's 80th birthday next week, or perhaps you recently went beyond the company's sales goal and exceeded expectations. Asking your boss for a raise, day off, or similar bargain can be stressful and awkward. But if you know how to ask your boss tricky questions, you'll have a better chance of getting them to agree. This guide covers some common questions you might have for your boss and how to ask them so you get a yes.

How to ask your boss for a raise

Who doesn't want more money? When you decide to ask your boss for a raise, it helps if you can show why you deserve one. Presenting data that demonstrates your achievements, ability to meet deadlines, or leadership skills is the best way to show your boss you're the ideal candidate for a raise. To justify giving you more money, your boss needs to see the value you add to the organization. Offer examples of your ability to increase revenue, decrease spending, or promote productivity.

Example: "Over the last three months, I've exceeded sales goals by 10% or more. This means I'm the top agent in the office, and I've been asked to mentor three fresh agents who are joining the team. I feel this new responsibility deserves a pay increase, which I'd like to discuss with you now."

"By leading the conversation with your accomplishments, you validate your ability to complete tasks that benefit the company and its goals."

Starting with facts and numbers gives your request credibility. Following your data statement, mention an achievement that sets you apart from your colleagues or new responsibilities you've taken on. Keep it short, let your boss know you want a raise, and begin the salary negotiation.

How to ask your boss for a day off

We all need a day off once in a while, but asking for one isn't always easy. It helps if you know your workplace's policy for requesting time off. Many employers require at least two weeks' notice for time-off requests. So, make sure you give plenty of notice when asking for a day off. The process may be as simple as emailing your boss and letting them know the dates you need to take off.

You can also give them a brief explanation of why you need the time off, which might be helpful if you're requesting a day off on short notice.

Example: "I'd like to request this Friday, March 23, off. I realize it's short notice, but the local animal shelter where I volunteer is having a pet adoption day, and another volunteer canceled. It would be great if I could step in and take her place, as they can't seem to find anyone else who can do it."

Your request should start with the day(s) you want off. Then, you can let your boss know the reason, giving some details so they understand how important the request is to you. For longer periods of absence, explain how your work will get done while you're away.

How to ask your boss for a promotion

So, you're ready to take your career to the next level? But how do you ask for a promotion professionally? Before asking for a promotion, consider why you want the position and how your skill set aligns with the duties of the role. Like asking for a raise, you'll want to show your boss why you deserve a promotion. Explain your leadership skills, discuss your career goals, and provide examples of your growth.

Example: "In the last year, I've overseen three successful projects, increasing productivity by 3% across the board. Currently, I'm working with the marketing team on a project we feel is only going to add to our success. This will require me to work extra hours and manage a larger team. I'd like to be put in a higher position on this project. Can we talk about my future with this company?"

By leading the conversation with your accomplishments, you validate your ability to complete tasks that benefit the company and its goals. You can then mention upcoming projects or those you're currently working on to show your commitment to the company's success. Let your boss know you're ready for more responsibility but you want the title to go with it.

How to ask your boss if you can work from home

Working remotely is becoming the norm, so asking your boss if you can work from home might not be a big deal. Think about your duties and which ones you can do from home. If you need to come to the office sometimes, consider asking for a hybrid working situation where you only work from home part-time. You could ask your boss about barriers to working from home and come up with ways to overcome them.

Example: "I know you said one of your concerns about letting me work from home was that I wouldn't be able to collaborate with my team members. The team and I discussed the issue and decided that we could get together weekly, either here at the office or at a location we all agree on. We believe we can manage the rest of our communications through email or video chats."

This conversation would be a continuation of one where you asked about issues with working from home. You can show your boss that you listened to their concerns while also letting them know you're a problem-solver who's willing to work things out.

Don't be afraid to ask your boss tricky questions, but make sure you're prepared for the conversation. If you're in the market for a new boss, create a profile on CareerBuilder so employers can find you.