A few principles to follow when approaching your boss: Express desires, not demands. Telling someone what you want him or her to do is far less effective than expressing what you’d love to see happen. Ask questions instead of making statements. Phrasing your request as a question rather than a statement almost always helps you go further. Make sure you’ve done everything you can do. You want to have maximized the factors within your control before you ask your leader about something beyond your control.