If you have a "Meet the Teacher" night, I have found that a great segue to set up a meeting a couple of weeks into school. The teacher is swarmed with parents all trying to quiz her, so if I take my turn to quickly suggest "I'm guessing you're having some challenges with DS about x and y?" And when she nods her head vigorously, I follow-up with "Maybe we could have a quick meeting to discuss how I can help you support his needs this year?", she always says yes. It seems a good way to make the meeting feel more teacher-imitated, and not aggressive-parent-pushed.
Granted, this tends to work because by two weeks, teachers always realize they have some challenges on their hands with my kids...
