How to Ask for a Raise without Being Annoying

Jake Wilder
6 min readAug 4, 2022

Don’t Let Your Boss Get Complacent with Your Salary

Photo: iStock

Let me tell you about a problem. Your salary is not based on your performance. It should be, but in most companies, it's not. Instead, it’s based on what your boss thinks will keep you happy and staying in your job.

It’s not right, but it’s the all-too-often reality. Managers want to retain talented people and they tend to pay more to those that they see as flight risks.

So, if you’re someone who shows up each day, does great work, and never complains, then your boss assumes you’re happy with your current salary. It’s easy for him or her to get complacent about it. Before long, he or she starts to justify spending a little more on someone else and little less on you.

Suddenly you’re making less than you deserve.

It’s one of the reasons that women earn, on average, 82 cents for every dollar that men do. It’s also why it’s important to remind your boss every now and then of how much you’re worth.

Don’t Complain. Make a Plan.

Let’s start with what not to do.

First, don’t just start complaining. Your goal is to raise your value in your boss’s eyes and few people value someone who whines all the time. The squeaky wheel may get the grease, until it’s replaced by one that simply performs without issue.

Second, don’t try to justify a raise with non-results reasons. I just bought a new house and need more money to cover the payments… I deserve a raise based on inflation… I used up all of my savings… My wife thinks I should ask for more money… I’ve seen people try to justify increased raises for all of those reasons and plenty of others. It never works out well.

Your salary is tied to your value. If you want to increase your pay, the best argument is to show that you’re delivering more value. And the best way to do that is to time your ask after you’ve had a big win.

Amidst the trove of management heuristics, availability bias has a starring role. It means that bosses will place more value on the work that’s easiest to remember. It’s why your performance in the three months leading up to your annual review tends to count for more than…



Jake Wilder

I don’t know where I’m going. But at least I know how to get there.