Asking your boss for more money is probably up there with doing your taxes and cleaning the gutters on your list of favorite things to do.

But salary freezes continue to thaw, and this may be your year to finally go for it.

At least it seems there’s a lot of money on the table for the taking. Compensation in the U.S. rose 1.9% from 2012 to 2013, according to the Bureau of Labor Statistics, and senior executives who changed jobs last year averaged a 17% compensation increase, found the executive search firm Salveson Stetson Group.

Ready to speak up for what you want? Here’s what you need to know to feel confident talking to your boss—from how much you should ask for to the best time to make your request—and finally score the raise you deserve.

How Often Should You Expect a Raise?

Salary upticks are typically granted only once a year, although it’s dependent on the mood of the economy and the demand for employees in your industry. (For instance, highly competitive fields like finance and tech are particularly raise-friendly.)

“It used to be the norm to expect an automatic annual raise, but after the economy took a nosedive, that has become less and less common,” says Alison Green, a former nonprofit chief of staff and author of the Ask a Manager blog. “Now you have to ask for more money.”

In general, there are only three instances when you can get away with a more frequent paycheck bump: if you’re an all-star performer and can make a strong case for why you deserve a raise sooner rather than later, you’re in a super-competitive industry like tech where the need for quality staffers is sky-high, or you work in retail or food service. (Raises tend to happen every six months or so in these fields, but it’s a tiny increase. Think: 20 cents an hour.)

Timing Your Request

Cliché as it is, timing is everything—and it can determine whether or not you’re rewarded.

First, consider when raises are generally granted at your company. Is it at the end of the year? On the anniversary of your start date?

Or maybe there’s no hard-and-fast rule that you’re aware of. “If you’re not sure, you can find out by word of mouth or by looking at the employee handbook—raises are usually tied to evaluations,” Green says. “There’s also nothing wrong with asking your manager flat-out. After you’ve been at a job for a while, say to him or her, ‘If I ever wanted to talk about my salary, how and when would that happen?’”

Many people make the mistake of asking for a raise during their annual review—but that’s probably too late. “Start talking to your boss about getting a raise three to four months in advance,” says writer and former human resources professional Suzanne Lucas of EvilHRLady.org. “That’s when they decide the budget.”

Typically, your company will allocate a certain amount of money for raises, which your boss must divvy up among his employees. Make sure to present your case for getting a bigger slice of the pie long before that decision has been made.

How to Ask for What You Want—and Get It

The way you initially bring up the subject of a raise depends on your manager’s personality, and you probably already have a sense of how she likes to be approached.

If your boss is the type who doesn’t beat around the bush, it’s best to make an appointment with a clear objective. Send a meeting invite or an email saying something like: “I’m hoping we can sit down, and I’d like to make the case to you for revisiting my salary.”

Other managers might prefer a more nuanced approach, where you broach the salary question in the context of another conversation, like a weekly status meeting.

When making the ask, be straightforward about what you want and prepare to explain exactly why you deserve it. “Be really thoughtful about it,” urges Green. “At its essence, a raise is recognition that you are now more valuable than you were—that your skill level has improved, that you’ve accomplished more.”

Tell your boss, “I was hoping we could talk about my salary. I’ve taken on a number of new responsibilities over the last year, such as [fill in the blank], and I’d like to discuss increasing my salary to a level that reflects that.”

Green suggests keeping a file of notes about your accomplishments to add to throughout the year—jotting down praise you’ve received, projects that were wildly successful and new tasks you’ve taken on—so that you have all the info at your fingertips.

Former ESL instructor Vanessa Wade used this strategy to score a raise, even though co-workers told her they hadn’t seen a salary bump in years. She knew how hard she was working and felt she should be compensated for it—so she prepared to discuss it with her boss. “Before I went to my supervisor, I made a list of highlights and what I achieved on behalf of the company and the amount of time it took.”

She explained that her students had learned English well enough that within three months, some obtained employment and got promoted, some created websites emphasizing their new language skills and others had poetry printed in an ESL newspaper. “I said to [my boss], ‘I give it my all, and my students have improved as a result. I’d like a raise to match what I have been able to do,’” she remembers. And it worked. Just a few weeks later, Wade earned a raise of more than 17%.

Cliché as it is, timing is everything—and it can determine whether or not you’re rewarded.

First, consider when raises are generally granted at your company. Is it at the end of the year? On the anniversary of your start date?

Or maybe there’s no hard-and-fast rule that you’re aware of. “If you’re not sure, you can find out by word of mouth or by looking at the employee handbook—raises are usually tied to evaluations,” Green says. “There’s also nothing wrong with asking your manager flat-out. After you’ve been at a job for a while, say to him or her, ‘If I ever wanted to talk about my salary, how and when would that happen?’”

Many people make the mistake of asking for a raise during their annual review—but that’s probably too late. “Start talking to your boss about getting a raise three to four months in advance,” says writer and former human resources professional Suzanne Lucas of EvilHRLady.org. “That’s when they decide the budget.”

Typically, your company will allocate a certain amount of money for raises, which your boss must divvy up among his employees. Make sure to present your case for getting a bigger slice of the pie long before that decision has been made.

This approach is especially effective for highly successful employees who have taken on additional responsibilities. Managers tend to know exactly what low-performing employees do because they have to follow up on everything to make sure it’s done right. But because productive staffers generally take care of their responsibilities on their own, managers may often be in the dark about their workload.

“You probably do a lot that your boss has no clue about,” Lucas points out. “You have to toot your own horn and highlight how you’re performing above and beyond expectations.”

Lucas experienced this firsthand while working for a former employer. When her boss went on maternity leave, she assumed half of her workload. Fast-forward six months later: Her boss still hadn’t returned, and Lucas was going above and beyond her job description … and building up resentment that she wasn’t being fairly compensated for it.

So she made an appointment with the head of her department and explained that she was doing more work than her position and title indicated—and deserved a raise to reflect her effort. “She completely agreed with me, and as soon as I brought it up, she got the ball rolling to get me a promotion and raise,” says Lucas. “She was a great boss, but because she’s so busy, my situation simply hadn’t been on her radar.”

What Kind of Bump Should You Expect?

Before you decide how much of a raise to request, do some homework. “If your company grants employees an annual raise, you’ll probably be aware of the approximate budget, so you should stay in line with that,” Lucas says. “Companies usually budget 5% or less for yearly upticks.”

Hypothetically, let’s say staffers at your company received an average of 2% more last year. Requesting a 10% increase will seem over-the-top and inappropriate, but if you’ve really excelled over the year, then a 3% raise might be reasonable.

No annual increase program in place? Then you need to do some more research. “So often people just go with their gut when requesting a certain figure and don’t have anything to back it up,” says Green. “You need to consider what the market is at a company of your size—for your skill level and in your geographic area.”

Skip sites like Glassdoor and PayScale—they’re too general—and instead figure out what salary you personally can command by talking to other people in your field, checking with recruiters (if you’re in an industry that uses them and have existing relationships) and scouring job postings (though not all listings include salary, some will provide a range) to calibrate your sense of market value.

One strategy is to ask for a “promotion in place.” “The idea is that although your position hasn’t changed, you’re taking on new responsibilities and deserve a new salary to go with it,” says Lucas. “For example, explain to your employer that you were at a ‘level 10,’ but are doing the work of a ‘level 12,’ and there’s a 10% salary increase between them.”

That’s the technique that Peter Anders*, who works in finance, recently used. His job title was manager, but he was performing at the level of a vice president. His company has a rigid employee appraisal system where staffers are given a list of goals they must achieve by the end of the year; and Anders’ tasks were in line with more seasoned workers.

After researching his market worth by talking to his network and to recruiters, he sat down with his boss and said, “I think I’m given a lot of responsibility here, which I really appreciate—and I’ve accomplished almost every goal that we’ve laid out for me to do. I’m curious about whether I’m performing at the level of someone higher up on the food chain. Can we explore whether I’m being compensated at the appropriate level?”

His supervisor told him he’d look into it, and, as a result, is currently in the process of upping Anders’ salary. “Rather than directly asking for more money, I posed the question about where I fell in the spectrum of other workers,” explains Anders. “That put the ball in his court.”

RELATED: Beyond Your Paycheck: 5 Things to Negotiate at Work

When you’re ready to talk numbers, there are two techniques: Name a specific sum or wait for your manager to mention it. There might be some advantage to the latter, according to Green. “[Your manager] might come back with a higher figure than you’d expected.” However, if the offer is lower than you’d like, tell your boss what you were hoping for and suggest meeting in the middle.

Whether or not to inflate your ideal sum a bit—under the assumption that you’ll negotiate to a happy medium—depends on your employer. “With some, that would be the exact right approach to take,” says Green. “With others, asking for more than is truly reasonable will make you look out of touch. You’ve got to know how the person you’re dealing with operates.”

Either way, prepare for the meeting with a target amount in mind—and that number depends on what you’re proposing.

“If you’re asking for a promotion, 10% isn’t out of line,” says Lucas. “If you’re just asking for an increase because you’re an awesome performer, 3% to 5% is practical.” (And it doesn’t matter whether you name a percentage versus a salary amount, although generally, a specific figure is the most direct approach.)

Remember that the sum is also tied to where you are on their scale. “Lots of companies have grades for each job, with a midpoint salary assigned,” explains Lucas. “If you’re below that midpoint, you can request more than if you’re above it.”

Playing the Counteroffer Card: Is It Smart?

Threatening to leave unless you get a bigger paycheck is dangerous territory.

While some organizations give nominal cost-of-living raises every year, the vast majority of salary increases are merit-based—not on whether you have an offer from another company. “The heavy emphasis of your ask should be on the value of your contribution,” affirms Green.

But it’s OK to hint at job retention in a subtle way, by saying something like, “I love the work I do here and want to stay with the company long-term. That said, my understanding of the market is that I should be making X.”

However, Green and Lucas agree that you should steer clear of asking your boss for a counteroffer outright. “Between 75% to 90% of people who accept a counteroffer leave the company within a year anyway,” says Lucas. “Once someone starts looking for a new job, it’s not just about the money.”

Even if your employer agrees to the counteroffer to keep you on board, it can leave a bad taste in his mouth. “Your manager knows that you have one foot out the door and could leave at any moment,” Green says. “So you’ll likely be excluded from the inner circle and end up getting pushed out.”

What If You Get a No?

Rejection is hard to hear, but don’t get discouraged. “Reply with, ‘What would it take for me to earn a raise in the future?’” Green suggests. “If she or he can’t tell you, that’s an indication that your manager is terrible or that the company is structured poorly.”

If your boss does offer an explanation, you now know exactly how to step up your game for the next go-around. It’s definitely not the end of the story.