I know that people have recommended books about education in the past. I hope people will indulge with my doing a variation on that. I've found that books on how to be a CEO and/or how to run a business, while not helpful for the day to day teaching of a tosfot or radak, can give insight into the big picture of running a school.
I do not subscribe to the thinking that schools are becoming businesses, but do think that there are universal truths for running any large organization (I actually found out about this book from a book I was reading about an NFL team, in which the head coach quoted the book to his players). The book I'd like to recommend is "Good to Great" by Jim Collins (it was a best seller when it came out and still sells well over a decade later). The book tracks several businesses that become "great" and tried to distill what qualities those companies had in common.
Many of the ideas in it are very applicable to schools. Ideas such as what qualities make for good leadership, the importance of honestly confronting hard truths about how you are doing, being cautious with new technology and avoiding "quick fixes" to real problems are certainly not limited to the business world. I will concede that 2 of the business described in the book have done poorly in the decade since the book came out (one of the criticisms that I've seen of the book), but don't think that there was ever supposed to be a guarantee that all the business would do well forever (not all schools that were doing well 10 years ago are doing well now, it's still worth evaluating what made them successful then).
Yaakov Blau
