Timing matters. Part of that means having the conversation when you’re in the right frame of mind to make your best case. And when your counterpart (your manager, HR, whomever) is in a good frame of mind to listen to and be persuaded by your case. You may also be in a good position to ask for a raise in the wake of a big win or milestone to which you made a clear contribution. One other fact of life in larger organizations can be the formal cycle for determining compensation and promotions. In some places, that happens once a year … and once decisions get hashed out and locked in, a manager may not have much ability (or appetite) to revisit the outcome. If you’re in a larger organization with a formal process, you should have a sense of that calendar so you can make your move at the right moment. What’s your experience with timing? Have you found timing factors that help … or that make it harder to get the terms you want?