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

CareerBuilder | August 3, 2022

Sticky questions for your boss

Not sure how to broach a sensitive topic at work? Take a look at these examples of tough questions to ask your boss, as well as how to ask and how not to ask.

Nobody really enjoys an awkward situation, and sometimes it's hard to decide when to ask certain questions in the workplace. Taking initiative and getting into a habit of asking important questions can make you look confident and professional, though it will also take finesse.

Talking to your boss about sensitive topics may be so awkward that you'll want to upload a resume and start looking at other jobs instead! Whether asking for feedback on a project or a weekend off, being honest but patient is key. Let's explore how to ask your boss a tricky question with these examples.

Asking about promotions

One of the best job promotion tips is to have a case for how promoting you would benefit the company. You don't want to come across as confrontational or hypercritical, like "I think I should get promoted because I'm the only one who can organize these people."

The better approach: You could say something like "Can we talk for a minute sometime about how I can reach the next level in this company?" Then, in the discussion itself, you can state your case for why you're due for a promotion and how it will strengthen the business.

Asking for a raise

A glance at CareerBuilder Salary Guides might reveal that the average person with your job has a higher salary than yours. If so, you can use this information to potentially get a raise, but you'll have to convince your boss that the work you do warrants more money. Walking in and demanding a raise due to others' salaries isn't the best way to go about this.

The better approach: Some of the best tips for getting a raise mention emphasizing the extra responsibilities that you've handled or noting your above-average performance. As an example: "In the past year, I've been asked to lead three new projects. I've met 10% above the expected quota, minimum, every time. Since that is going to continue, can we talk about lifting my salary to make it more in line with my performance?" This also works well if you're not sure how to ask your boss about your bonus.

Asking to switch to remote work

Remote work continues to grow every year. The work flexibility of the internet can be very appealing to workers and save businesses money. Getting more work flexibility is likely to work if you can make it about your schedule and your output. Saying, "How come I have to come in every day but half the office doesn't? I want to switch to working from home" probably won't start the discussion in your favor. It also helps to ask for these things in small steps and to propose trial periods.

The better approach: "I have a work style and personality that is ideal for working at home. I think a trial run would go very well and demonstrate what I mean. Can we talk about my plans to work remotely and perform better?" As usual, broaching the possibility of discussing it when the manager has time is more likely to work than pushing for an answer.

Asking for a day off

Stuck on how to ask your boss for a day off? Going in and simply asking "Can I take Friday and Monday off? I'm going out of town" might not go over so well. It doesn't have to be a big deal, and many workplaces will accept a formal request via email. If you're not sure how to request something from your boss in email, like time off, the important parts are the same: ask as early as possible, explain the reasoning for your request, and try to work with the company's schedule.

The better approach: Lead with the request instead of the reason, and then move on to briefly explain. "I would like to request some time off on the 12th and 13th of next month. I will have jury duty, but I'm prepared to get our latest projects done on their due date of the 10th as usual, and I already have a head start on the upcoming project. I think we're more than covered for my absence, but I'm happy to talk more if there are any doubts or questions about getting everything done."

If you're not sure how to ask your boss for a promotion, a change to your work situation, or other things, the pressure might cause you to never speak up. You'll be glad you did, though, especially if you calmly broach a difficult topic. Not only will your hiring managers appreciate your social grace, but it will establish you as a go-getter.

Advice for talking to your boss:

See the other side by learning how to answer your boss's tricky questions.

See our guide on how to tell your boss you made a mistake.

Don't lose your temper and say things you should never say to your boss. Use these tips instead.

Why you should stop apologizing at work and what to do instead.