Everyone's school situation is different, but somehow we all need to get our shows selected and scheduled- here's my recommendation: don't wait. Start now. Think about what you want to do next year, what plays you want to present and why*. Even if you won't announce your season until next fall, don't put off choosing the plays until then.
Sometime in the next month or two, your school will be putting together the academic calendar for next year. Get ready. Figure out what dates you want. Choose plays. Lay them out in a season. Choose as many plays as you can, and choose back up plays in case you have a problem. If there is a scheduling meeting before you have selected your plays, just use place holders like Fall Play One, Fall Play Two, Spring Musical, One Act Play Festival, etc. It's easier to overbook and trim your dates back than it is to try to add dates when the school year is in full swing. Apply for the rights as soon as you can, too.
Here another tip: if you must have your plays approved by someone, get a stack of perusals together. That way you can take them in to your Admin, or whoever it is that approves plays, and say something like: "I know we normally only do three plays a year, but to make the selection easier, here are copies of ten plays I am considering. Could you look at them and let me know what you think? I'd like to have plays selected by the end of the month." I have known many principals, administrators and department heads, some were great theatre supporters, some were suspicious of the arts in general, but none of them had the time to read a stack of plays. They will eventually learn that it is much easier to trust you.
As far as when you should announce next year's season, I always did it in the program for the pervious Spring Musical, since that was always my best attended show.
Remember: the people who go to the theatre are the people who go to theatre. Go out of your way to let them know what shows they can see next year.
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