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What is typical % of bonus at end of year
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I don't think there is ever a good time to ask for a raise in this economy. I would go for it if you feel like you aren't being paid what you should. It never hurts to ask, especially if you can back up why they should give you a raise.
The worst they can say is no, but unless your skills are extremely in-demand, there is no reason for them to say yes. I would be prepared to make your case and give it a try, just don't hold your breath.
The way to do this is a year in advance. During your review ask what you can do to become a more valuable. Be honest that you want to grow your career, and let them know you’re willing to be patient. At six month mark check in and get feedback on your progress. 3 months before review is often when raises are determined, and formal feedback is then layered in. If you’ve really added value, that’s the time to remind people.