There seems to be broad agreement in Western education systems that educational reform at the school level is urgently required. Much of the recent literature in educational administration posits particular styles of leadership as being an appropriate means for achieving school reform and improvement. This chapter argues, however, that the predominant conception of ‘new’ leadership as a moral and cultural enterprise is inadequate because it tacitly assumes a functionalist perspective within which the nature of school relationships is misunderstood. Moreover, an undue emphasis upon the role of administrative leaders in schools suggests that it is possible to reduce complex educational problems to administrative issues that are represented as being soluble at the school level. Many educational problems, however, can only be understood in relation to the broad social, political and cultural context of which education is a part. An alternative conception of leadership, one which appreciates educational complexity and facilitates critical scrutiny of school problems such that connections are explicitly made between the educational sphere and other spheres, is required.