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You’ve probably heard that, more often than not, you need to speak up and ask for a raise—it’s not just going to be given to you—and that’s a good thing.

But, it is possible to jump the gun. Even when you know you’re performing your responsibilities well beyond the job description, that doesn’t necessarily mean it’s time to march over to your manager’s desk for a little chat. Asking for a raise is an important step in managing your career, and it’s something you should plan carefully. And sometimes, timing is everything.

Remember that just because you think you’re ready for a raise, it doesn’t mean your boss—or your company—is ready to give you one. Ask for that raise at the wrong moment, and you might find you’ve inadvertently put yourself on your manager’s bad side—instead of impressing her with your confidence in your value.

If you’ve decided you’re ready, you need to know how to ask for a raise. But, before you start practicing your pitch in the mirror, here are a few questions you should ask yourself to assure your boss is ready, too.

1. Have You Been There Over a Year?

Maybe this seems old-fashioned, given how often people change careers—but in my experience, I’ve found that the one-year mark still seems to be the standard by which most managers distinguish the “probational” employees from the veterans.

If you’re just entering the job market, one year may seem like an eternity, but put yourself in your boss’ shoes. How long have they been there? If your boss has five, or even 10 years on you, asking for a raise before your first-year anniversary could make you come off as entitled—even if your manager is thrilled with your performance.

When I first became a team lead, I was a little stunned by how quickly my employees expected advancement. Every manager has been at the bottom, and there’s still something to be said for “putting in the time.” Whenever I had an employee ask for a raise after only a few months on the job, I immediately felt she didn’t respect or understand the full spectrum of her responsibilities.

Unless you’ve been given specific guidance about an accelerated timeline for promotion, it’s a safe bet to assume you need to give the job at least one year before you—and your boss—are ready to start talking money.

2. Is the Company in Transition?

If your company is in transition—for example, going through a merger or a company-wide restructuring—it’s generally a bad time to be asking for more money. It’s a real bummer of a situation, because, unfortunately, it’s completely out of your control. But, the best course of action is almost always to sit tight, keep working hard, and wait for the dust to settle.

At one point in my career, I worked for a firm that had been through three major mergers—and a few minor ones—during the several years I was employed there. And, as is often the case with this type of thing, the staff was reduced, meaning that those of us lucky enough to keep our jobs were suddenly responsible for the work of three.

At the time, the increased workload seemed like the best rationale for a raise possible. My company was getting three (or more) employees for the price of one! What I didn’t consider, however, was that my manager—along with all my colleagues—were also stretched pretty thin, and money was tight.

Luckily for me, my manager recognized that I was just young and inexperienced and proceeded to explain to me how my request might be taken negatively during a time when everyone was working hard.

I adjusted my attitude, and refocused my energy on the success of my team, rather than just on myself. Not only was this rewarding, but it made a great impression on both my boss and my colleagues. And guess what? At the end of the year, there was no need to ask for that raise.

3. Are You Exceeding Expectations—Or Just Meeting Them?

Once you’ve put in the time, and chosen a time when your employer isn’t in dire straits—that means you’re good to go on scheduling that one-on-one with your boss, right?

Almost. But there’s one final question you need to consider, and, of course, it’s a tough one: Are you exceeding your boss’ expectations—or just meeting them? Answering this question is harder than it may sound, and it requires a lot of honest self-assessment—but trust me, you’ll be glad you took the time to reflect on this in a meaningful way.

Back in my management days, I had an employee who jumped the gun a little when she approached me to ask for a salary increase. While I agreed she was doing a good job, she wasn’t yet blowing me away, and I didn’t feel a raise was appropriate. Explaining this to her was not fun for me, and I imagine it was even less fun for her. If she would’ve taken some time to consider how she measured up to the expectations of her role, she might have saved us both a really awkward conversation.


Asking for a raise is one of the most difficult things to do in the workplace, and so it’s important to take steps to set yourself up for success when you do. And, in addition to doing your negotiating homework, that means making sure you consider your boss’ and your employer’s perspective when you ask.

And, if you determine that now might not be the right time to ask for a raise, don’t get discouraged—now can still be the start of a dialogue with your boss. Let her know your goals, and get her feedback on what you need to do to get there. You’ll demonstrate your leadership potential, plus you’ll start warming her up for the day you’re really ready to ask for that raise.