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With all the baby-boomer heads retiring now or soon, the overarching question of who will lead our schools in the coming decades hangs in the air. It also raises questions about how schools make successful transitions from one head to another. What do boards need to know in order to choose the best leader for their school’s future — especially when the landscape seems to shift yearly? How can schools ensure that the transition process goes well? How do search committees weigh the varying qualities of a diverse group of candidates? What should they ask of search firms? How can schools leverage the leadership transition to strengthen the community? For their part, what can outgoing heads do to make the transition smooth?