It's that time of year again: a time to wrap up year-end projects, check key goals off your list, and face the often-daunting but necessary process of negotiating a raise at work. But rather than dive head first into that discussion, be sure to run through the following questions ahead of time.

1. Am I actually underpaid?

Though you might feel entitled to a pay boost based on your skills and effort, the reality is that if you're not statistically underpaid, you might have a harder time arguing that point. Before you attempt to talk numbers with your boss, do some research to see if your earnings are on par with those of the average person who has your job title. If they are, or if you find that you're being paid rather generously within your field, you'll need to adjust your strategy when having that salary discussion.

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2. Have I done anything to deserve a salary boost?

It's one thing to want more money, but it's another thing to legitimately merit an increase. Before you ask for a higher salary, think about whether you deserve an increase. If you've consistently worked late, pitched in on projects that technically weren't your responsibility, or added value to your company in another way, then by all means, make the case for a boost. But if you can't think of a single compelling reason why you deserve a raise, you might want to table that discussion for another time.

3. When's the last time I got a raise?

There's no rule stating that you must wait a certain period of time (such as a year) between raises before you ask again. For example, if you got a raise in July along with most of your peers but your scope of responsibilities has increased since then, there's nothing wrong with asking for more money five months later. At the same time, if you got a raise two months ago, there's a good chance your boss will look at you funny if you initiate a salary discussion in conjunction with the close of the year.

On the flip side, if you've been doing the same job for the past three years without any sort of income boost, you can make the argument that while your responsibilities may not have shifted, there comes a point when you need a boost to keep up with the general cost of living. So if it's been a while since your pay has changed, get that meeting onto your boss's calendar.

4. Are there benefits I should ask for instead of a raise?

It's always nice to get more money, but before you insist on a raise, think about whether there are some workplace benefits it pays to request instead. For example, if your 401(k) plan is lousy and your employer doesn't provide a match, you might ask for an improvement in that area instead of a $2,000 bump in income. And while an uptick in vacation days won't necessarily put more money back in your pocket, if your company has been stingy on that front thus far, snagging an extra week of paid time off might do more for you than an extra $1,000 or so in earnings.

5. Should I actually ask for the amount I want or aim higher?

One of the toughest parts of negotiating a raise is determining what number to ask for. If you present the salary you're actually looking for, there won't be room for your company to negotiate downward. On the other hand, if you aim too high, you might come off as greedy. A good compromise, therefore, is to ask for slightly more than the number you'll actually be happy with. For example, if you're hoping for a salary of $58,000, ask for $60,000, because chances are your employer will try to take that figure down a notch.

6. What will I do if that conversation doesn't go my way?

While it's good to approach a salary negotiation with a positive attitude, you'll also need to account for the possibility that your request for more money could get outright denied. That's why it helps to go in with a backup plan. Before sitting down with your manager, think about what you'll do if that discussion doesn't go the way you want it to. Will you ask for a different accommodation (such as the ability to work from home) as a compromise? Or will you nod politely, exit the room, and immediately fire off your resume? Knowing what you'll do in the face of rejection will help you better navigate that unfortunate but possible turn of events.

Talking salary takes guts, but it also requires some forethought. Run through these questions before having that talk so you're better equipped to handle what could be a lucrative, albeit stressful, conversation.

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