Although I am somewhat less enamored with him now that I used to be, I think John Taylor Gatto's list of 14 things that elite private schools teach that public schools don't is by far the best list of things to focus on for high school age kids:
Gatto's ideas about education are based on history and spirituality (esp. Christianity) rather than science, which can be somewhat offputting at first, but having read the best of the sciency books on the various aspects of childhood development and education I generally think Gatto has more to offer. (Not that the other books aren't good too, but they're generally more useful for designing education systems that scale rather than parenting, except for when the kid is less than five which it doesn't sound like yours are.)
