Just what should the public expect from the leadership at the school district level? Why does it seem to be eternally controversial in many places, especially in urban districts? What difference could achieving "the right fit" between superintendents and school boards make in the learning of children? Currently, most of the attention on reforming schools focuses on classrooms. The reasoning is that dedicated, well-qualified teachers can boost student achievement despite the chaos swirling outside their classroom doors. Ideally, they work under a principal who provides them with the right mix of support and autonomy. This paper looks at the relationship between school boards and superintendents and how it affects student achievement. A bibliography is included.