I'm on year 2 and just asked for a raise for the first time ever. Nervous and hopeful about the outcome, which my manager said I'd hear about on Monday. If you're the kind of person who likes to spend at least 5 years in a particular company, how often would you ask for a raise?

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Raises should be annual at a minimum period I think they should be standard for everybody and we shouldn't have to beg for them. It's very frustrating how companies do that!

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At least annually. If they’re reporting their earnings quarterly it’s only normal I ask frequently.

Annually!!

Annually and I would bring it up after to hit major milestones or taking on new responsibilities

Asking for a raise after two years sounds very reasonable. If I planned to stay five years, I’d probably aim to have that conversation every 12–18 months, tied to clear results and responsibilities.

Every single year. No exceptions.
Loyalty doesn't pay your rent — and companies rarely volunteer money they don't have to give. If you're not asking annually, you're likely falling behind inflation while your market value keeps climbing.
The math is brutal for long-tenured employees: internal raises average 3-5%, while external moves yield 15-30%. Stay five years without negotiating aggressively and you're potentially $40-60k behind someone who job-hopped once.
Annual reviews exist specifically for this conversation. Come prepared with your wins, market data from Glassdoor and LinkedIn, and a specific number — not a range. Ranges get rounded down every time.
Good luck Monday. Whatever the outcome, let it tell you something about how this company values you — and plan accordingly.
How long have you been at your current salary — any idea where you land relative to market?

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