At this time of the year, you may be thinking ahead to a conversation in December with your boss about compensation.  But that’s a big mistake.
Every December I get flooded with questions like “what should I say at my end of year meeting next week to negotiate a raise” and the truth is that’s likely too late to create any real change. Budgets were probably finalized weeks ago by a bunch of execs who sat in a room talking about who on the team has stood out and deserves to get the limited funds that are to be allocated for raises and the message gets delivered to you in that review meeting. That means if you want to be the one they’re talking about you need to start getting them thinking about you NOW.
Starting now also lets you engage in a much more powerful conversation with your boss, one that’s ongoing and will lead to success. But how the heck do you do it?

Schedule a check-in with your boss.

Position the conversation as collaborating by calling it a check-in or feedback session noting that you’re looking for guidance on how you’re progressing toward your year-end objectives. Of course, the earlier in the year you do this, the more opportunity you have to course correct in case of any surprises so get in their calendar ASAP. By engaging your boss and asking them for the feedback it’s a compliment for their ego (who doesn’t like being asked for their expertise) and makes them part of the process and thus more accountable to your success. It could sound like this: “Hey boss, I wanted to loop you in on a few things I’m working on and get your feedback, when is the best time for us to meet this week?” 

Consider the WHY from their perspective.

The goal of the meeting is to get them familiar with all of your accomplishments, but you want to do it in a way that answers the question “Why should I care?” Talk about your actions in a way that highlights your contribution to the company goals or perhaps to your boss’ department objectives. Consider how your work makes their life easier to make them engage. To avoid feeling too braggy and to sound more objective, provide positive feedback from others that you’ve received—especially if your boss is someone who gave it to you. It’s more compelling if it came out of their mouth. Don’t think you have any? Check your email! In fact, I recommend you save every compliment or message of encouragement in an email ‘Feel Good’ folder so that you have a collection of third party endorsements when you need it for reference—plus re-reading it will also give you the extra confidence boost in that meeting.

Get proactive with your WHAT.

Review what your goals were at the beginning of the year and ask for specifics about how you’re tracking against them. The objective here is to reinforce that you’ve actually been doing quite well and that you deserve that raise, not necessarily to move the goal posts. When they go to advocate for you in a few weeks you want to make sure your positive progress is top of mind for them. Don’t give them any room to be vague, have questions ready like “what does success look like to you? What kind of milestones would you anticipate?” Get specific markers that you can speak to in a few months time—preferably markers articulated by them so there’s no question about whether or not you’ve accomplished those goals.

Ask HOW you can work with your boss to make it happen.

If you work out a plan that engages your manager in the process they’ll feel more invested in your success and they’ll also feel more accountable to make the plan a success. If you look good, they look good. This also opens the door for you to circle back for pointers if needed. “I’m working on that activity we planned and I’ve got some questions about it.”

Make your expectations known.

As you’re having these conversations make sure you articulate your intentions—that you want to make sure you are maximizing your potential and advancing your career. Of course along with that comes the compensation to make sure that you are rewarded accordingly. When it comes time to talk about the details, you’ll put yourself in the strongest position by starting with revealing objective information you’ve gathered about compensation and career paths in the industry overall, and how you expect to align with them. It’s not about “I think” and your opinion. It’s “I know” based on facts you’ve collected from your research on what others are making in your field and industry. “Based on what I’m seeing in the market I would expect…” is much more credible than “I think I deserve…” They can’t deny facts and they’re going to have to work hard to either make your compensation competitive or give some solid reasons why they might not be able to if they’re going to maintain credibility. 
When you’re well prepared and you start the process early you’re far more likely to get that raise. Great negotiators don’t wing. Do your homework and remind yourself of what you bring to the table and you’ll be able to make others recognize it too!