If you’re as awkward as I am (very), speaking to authority figures is not exactly a walk in the park. Maybe it’s because my generation has been raised (to uncondiatally accept adults stepping all over us), but something about communicating with people above me makes me deeply uneasy. I’ve always been on good terms with the bosses I’ve had, mostly due to putting my nose to the grindstone and avoiding drama. There are times, though, when you need to communicate with your supervisor, and asking for a raise is one of them.
I’m not going to lie to you: it’s going to be awkward. I’m going to take a leap of faith and assume that you’re asking for a raise for a legitimate reason (working overtime, extra responsibilities, a change in lifestyles) and not something trivial (you’re just broke, you don’t like your manager, you think your coworker’s obnoxious). Bosses have to watch out for their businesses, and that includes being fiscally responsible, which means that giving employees a raise isn’t always something they can fathom. Make sure you have a solid argument for why you deserve one outlined before you ask for it–if even you don’t know why you would be granted a raise, your boss won’t either.
Be polite but firm, kind of like you’re training a dog. Groveling is super unattractive and will make you seem unprofessional–no matter how much you need it, don’t forget to keep your dignity when you’re asking for a raise. If possible, have at least a week’s worth of statistics ready–hours you’ve worked, sales you’ve made, etc. Bosses tend to give raises to employees who are organized and professional; even if you’re not either of those things (I’m probably the least organized person ever born into this world), fake it until you make it. Telling people what they want to hear to be ahead isn’t the same as pandering–besides, if you can’t sell yourself, you’re pretty much up the creek.
Don’t take it personally if you don’t get it. In all likelihood, it’s because of company issues and not a reflection of you as an employee. Patience is key, and if you’re persistent in why and how you can earn a raise, there’s a high chance you’ll be granted one eventually.