Talking to Your Boss: An Agenda for Asking for a Raise
How to prepare your case and gain the confidence to get the paycheck you have earned

Asking for a raise can feel uncomfortable, even for confident workers. Many people worry about sounding ungrateful, being told no, or damaging their relationship with their manager. As a result, employees often wait far too long to bring up the conversation, or don’t have it at all. Nearly 40% of workers have never asked for an adjustment in compensation, according to FlexJobs.
The reality is that raises are rarely automatic. Managers are juggling budgets, priorities, and dozens of employees, which means your accomplishments can easily be overlooked if you don’t advocate for yourself. Even more simply: you rarely get what you don’t ask for in life.
That’s why it helps to treat the conversation like a meeting with a clear agenda. WorkMoney put together a guide on how you can speak with your manager about a raise, and ensure the meeting is properly structured to give you the best chance of making more money.
Why Asking for a Raise Feels So Difficult
On the employee side, it comes down to one simple, yet powerful emotion: fear. 32% of Americans say they don’t know how to approach the conversation and 28% say they’re afraid of hearing no, according to a 2023 survey.
There’s also a structural reason these conversations feel difficult: many workplaces don’t normalize them. Performance reviews may focus on feedback or goals rather than compensation, leaving employees unsure about when or how to bring up pay. Without clear guidance, workers often assume raises will happen automatically if they work hard enough.
So if you feel like you’re ready to have the conversation, here are the steps to prepare:
The Cost of Doing Nothing
Choosing not to ask for a raise may feel like the safe option, but it comes with a real financial cost. During periods of inflation, your money gradually loses purchasing power, even if your salary stays exactly the same.
For example, if inflation is running at 4% and your pay doesn’t change, your effective income has effectively declined by 4%. Over time, that gap adds up, making everyday expenses feel more expensive without any increase in earnings to offset it.
Asking for a raise isn’t just about getting ahead, it’s about staying even. It’s a way to protect the value of your work and ensure your income keeps pace with the rising cost of living.
About the Author

Brett Holzhauer
Brett Holzhauer is a Certified Personal Finance Counselor (CPFC) who has reported for outlets like CNBC Select, Forbes Advisor, LendingTree, UpgradedPoints, MoneyGeek and more throughout his career. He is an alum of the Walter Cronkite School of Journalism at Arizona State. When he is not reporting, Brett is likely watching college football or traveling.


