I know his type. He loves playing to your emotions: “I work all the time; why should you get to drink daiquiris in the Whitsundays?” Your play? Take all the emotion out of it. Use email and just write, “I’d like to request annual leave days from February 15 to 22, as well as April 13 and 14. Thanks.” You’ve earned the time – and don’t let a soul tell you differently.