Educational leadership, as a field of both practice and inquiry, has undergone remarkable growth over the past 100 years. From relatively modest beginnings related to a religious and moral emphasis in schooling, thought and practice, it progressed through the eras of scientific management, a focus on humanistic values, the theory movement, the postmodern and critical theory turn of the 1980s, the social justice movement and neo-accountability (Brooks and Miles, 2008; Callahan, 1962; Cuban, 1988; Glass, 1986; Tyack and Hansot, 1982). To be sure, I am painting with a broad brush here – there are multiple perspectives on whether or not these eras offer a fair characterisation of the field of educational leadership; ideas born in each of them have later resurfaced (or disappeared), and antecedent ideas and practices from each of these times continue to influence the field to varying degrees. This chapter is less an exercise in looking backward and more an attempt to describe a perspective and to critique the present from that perspective. I begin the inquiry with a provocative question and, over the course of the chapter, explore possible answers and the many questions that such a question raises.