15 (Legal) Ways To Talk Your Boss Into Giving You A Raise Photo credit: Bigstock 2. Schedule a Sit Down Asking for a raise is not the kind of conversation that should take place when you’re sidling up beside the big boss at the urinal or when you have him trapped in the elevator. At best your boss will be irritated and at worst, you’ll come off like a creeper. Schedule a meeting, and before you go in, you had better… Prev2 of 16Next Facebook Comments comments