Measure the Tone of Your School
Let's face facts--not all schools are created equal, and not all administrators have a sense of humor. What might get you a wink and a smile from one principal might get you expelled by another. One good strategy is to make sure whatever you do can easily be undone. Another is to play to things you know your administrator has a soft spot for. Remember, virtually every person in education was a geek of one sort or another at one time.