The best time to ask for a raise is the day after your boss and you have agreed to one.
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At that point, your boss will be exhaling for having gotten through a possibly awkward raise conversation that may or may not have left you feeling upset or disappointed. Ask your boss if you can sit down with them and ask a hypothetical question that has nothing to do with the raise you just received. Hopefully, they will agree.
When you meet with them, say, "I'd like you to imagine you're at your next performance review, and your boss is reviewing you and your decision making and the judgment calls you make regarding your people – in this case, me. I would like you to imagine that you say to your boss, 'By the way, what is the maximum raise we can give [your name] the next time raises come up? I would hate to lose [your name] or have them poached away.'"
"Now please tell me as specifically as possible, what is it that I can accomplish, achieve, and just plain 'get done' going forward that would cause you to go to bat for me that way?"
After they respond to this question, say: "This is much too important to me to misunderstand a word you just said, so I'm going to repeat back to you what I heard you've told me I need to accomplish, achieve, and get done for you to go to bat for me. What I heard you said is, [repeat back to them exactly what they said]. Is that correct?"
When your boss gives you the affirmative "Yes," it will deepen their commitment to what they have agreed to.
Then, provided the boss has agreed with what you just said, respond with, "Thank you! Going forward, I'd like to check in with you every month to see if I'm on track to meeting your expectations. What would be the best way to arrange that?"
One final reason on why you might want to take this day-after approach: Knowing that you have this plan can actually help you to be less upset with however your raise conversation went. Furthermore, being gracious during that conversation can make your boss more appreciative of you when compared with the people who don't react so well to bad raise-related news.
And your takeaway from this? Focus on the future, where you haven't yet been upset or disappointed, instead of reacting to something that has happened and caused a very awkward conversation.
For more suggestions and strategies on how to get out of your own way on your path to career success, please check out Recruiter.com's first course online course, How to Get Out of Your Own Way at Work with Dr. Mark Goulston.