Career Tip #35: The thought of asking your boss for a raise may raise your blood pressure, but here are a few tips to help you be successful. Choose your time wisely – after the successful completion of a major project, a banner billing quarter or a large sale. Do your homework on typical salaries for your position and have that information with you. Prepare to speak on how you have impacted the company and its bottom line with concrete examples. If you are turned down, ask what it would take to earn that raise.