How to Ask for a Raise When You Hate Talking About Money

January 13, 2016

By Melody Wilding 

Talking about money can be difficult, even scary. It’s a topic that makes a lot of people feel uncomfortable. Whether you’re negotiating higher pay in a new job offer or vying for a promotion in your current role, discussing salary is downright stressful. 

You’re afraid of getting turned down, making things awkward, or even offending your manager. So, you make excuses as a way to sidestep the conversation. You tone down your requests—or worse, you don’t ask at all.

While your fear of talking about money may help you avoid discomfort and confrontation, it can seriously hold you back in your career. The short-term discomfort is a small price to pay for reaching your full earning potential in the long run.

The four strategies ahead will help you overcome your anxiety and ask for the raise you deserve.

1. Pinpoint Your Money Stories

The way we feel and think about money is learned behavior. If you come from a background in which finances weren’t openly discussed or in which they caused conflict, the thought of asking for a raise may make you feel especially anxious. 

What messages, ideas, and attitudes about money were conveyed to you growing up? Reflecting on the conversations you had when you were young will lead you to recognize the source of your anxiety and ultimately help manage it. Uncovering your financial story enables you to dismantle limiting beliefs one by one and help release their emotional power over you. 

For example, if you agonize over student loan payments or beat yourself up for splurging on lunch, pay attention to how that negative self-talk drags you down. Work on re-wiring your vocabulary to eliminate language like this, and replace it with thoughts on how your earnings help you feel independent and capable. 

2. Get Comfortable With Discomfort

Think of assertiveness as a muscle; you need to work it out and develop it before you’re ready to use it. No one becomes a master negotiator overnight. 

The first time you talk about money (if it’s a topic you avoid) shouldn’t be the meeting you have with your boss where you ask for salary bump. Start small and save the high-stakes discussion for when you’ve reached a certain level of comfort when it comes to the M-word. 

Noah Kagan, entrepreneur and founder of AppSumo, suggests taking on a coffee challenge: Walk into a coffee shop and ask for 10% off your purchase, just because. It may sound daunting to ask a complete stranger for a discount, but it won’t kill you. The trick here is not to worry about getting a yes—though, surprisingly, most times you will (seriously, try it!)—but rather to force yourself out of your comfort zone. This type of discomfort is the secret to growth and mastering difficult conversations.

The more you practice, the easier and more natural talking about finances will feel. 

3. Prepare the Right Way

While preparation—putting together revenue charts, documenting comparable job salaries, proposing a work plan—is key when asking for a raise, over-preparation can backfire. 

In fact, the practice of over-preparing is a common protective mechanism for managing anxiety. But, if you don’t develop authentic confidence and solid negotiation skills, no amount of preparing is going to pay off. 

For example, let’s say you spend hours rehearsing exactly how you’re going to ask for a raise until it’s cemented in your mind. If, for whatever reason, your boss goes off the imaginary script you wrote for him or her, it’s likely you won’t know how to respond. 

Try creating conversational “headlines,” or key areas that justify your argument and build up to your request. Here are a few examples:

  • I’ve been working with this company for a long time and here are my successes so far…
  • Here are several other ways I intend to help the company in the future…
  • In order to compensate for all the extra time and effort I’ve put in to date and the quality work I’ll continue to provide…

Your goal is to make a clear case for your request and get your boss to give you a well-deserved raise. 

4. Channel Your Career Hero

Another great strategy for moving beyond self-conscious thoughts or self-doubt is to invoke your personal hero. If, after all of the above advice, you’re still apprehensive, try thinking about what Oprah,Sheryl Sandberg, Mark Cuban, or the mentor of your choice would do in this situation. What would this successful person say in a similarly difficult conversation? How would she act and how would she carry herself? Not only will the thought of Oprah asking your boss for a raise make you smile, it’ll help you begin to problem solve and see the situation in a fresh light. 

Another way to get over your anxiety is to develop a persona or alter ego. Imagine how you would act if you were able to put all of your fears and inhibitions aside: How would you carry yourself? What would you say? Adopt the posture, body language, thoughts, and feelings of your new character in your next meeting or while out with friends. This type of role-play will help you get a feel for how people are likely to respond, and you’ll be better suited to approach your boss when the time comes.


Asking for a raise isn’t about having a confrontation; rather, it’s about creating an opportunity to seek what you deserve. 

If your request for a raise is denied and no reason is given, take the opportunity (hey, you’ve gone this far) to ask open-ended questions about your performance and the reasons for the rejection. Inquire about when you can have a follow-up conversation. Rejection of any kind is difficult to swallow, and if you’ve psyched yourself up, it can be even harder to handle. But, for a potential raise down the line, you’re going to have to keep working your money-talk muscle and building up your confidence. The conversation is far from over.

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