Anyone who has ever had a job has dreaded this one conversation and wanted to know how to do it better — asking the boss for a raise.

You know you owe it to yourself to ask for a salary bump now and then, especially when your work is outstanding. But you might not be confident how to best go about it.

Fortunately, there are experts at navigating such treacherous career waters. Here are five tips from career coaches, executive coaches and recruiters on how to ask for a raise.

1. Have a plan for this conversation

This isn’t a conversation you just wing.

“Know things like the time frame you’ve been there, your highlights and successes, and any additional skills you’ve acquired in that time,” says Tim Simons, owner and CEO of Build Coaching in New York.

Have talking points prepared and in front of you for your meeting. “This helps keep your thoughts together during a nerve-wracking conversation,” says Debbie Lawrence, founder of Talent Forward HR in Charlotte, North Carolina.

2. Know your worth

Knowing your worth is the biggest thing, says Gina Crook, senior recruiter for TransTech IT Staffing in Chicago. You don’t want to ask for too much (and risk not being taken seriously) or too little (and undermining your worth).

“There are a lot of great tools out there, such as Glassdoor, that will provide you with a market analysis of what you should be making based on years of experience and where you live,” she adds. 

Lawrence recommends knowing the salary range for your position, which you can get from HR and perhaps past annual reviews. She also advises politely asking colleagues about a range you have in mind, though this might be easier to do with friends in similar positions at similar companies.

3. Get the timing right

“Make this its own conversation. Don’t add it on the end of some other conversation about a client or work task,” Simons says.

Also, make your case well ahead of your annual review, says Denise Kalm, career coach at DPK Coaching in Walnut Creek, California. “Raises are already figured out, and there is usually no money left if you weren’t already on track for a raise.”

Your midyear review might be a good time to have this conversation as it leaves enough time for you to make your case, even strengthen your case and for your boss to advocate for you, which leads to …

4. Be a problem solver

It pays to be a problem solver, not only in the work you do for your employer, but in how you advocate for yourself.

“Let’s assume the best case. Your boss loves your work and would love to give you a raise. What do you think is preventing her from doing it?” says Guillermo Villar, executive communication coach and founder of Cambio Coaching in Charlotte. “Ask yourself or her what could help her argue for a raise on your behalf. How could you arm her with the information to sell the raise to her manager and to HR?”

5. Follow more than just the money

If a bigger paycheck isn’t in the cards, don’t end the conversation. “You can still make the case for something else that you’d value,” Villar says.

Think about why you want the raise, what more money would allow you to do.

“Would it allow you to take care of some things that you’ve been neglecting? Maybe having more personal time to take care of those things could also help, and your boss might more easily negotiate alternate working hours with you than get you more money,” Villar says.

He also noted you could explore a change to your bonus structure or even a new title that would set you up for your next job. Just don’t make it sound like you are leaving anytime soon.

The bottom line

“Don’t be afraid to ask,” Crook says. “You cannot get something if you do not ask for it.”

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