1. It's bad to ask for a raise If you and your company are performing well, it is never bad to ask your boss for a raise. Your boss may have room in the budget to reward a stand-out employee, even if it is not typical raise or bonus time. If you feel as if you are being underpaid, it is also smart to obtain market compensation data from tools such as The Salary Wizard and the Personal Salary Report to offer your boss hard evidence as to why your should be paid more. Nothing is going to happen unless you take the initiative.