This article explores a paradox, namely the rhetoric of engagement with diversity and social justice among education leaders, yet the paucity in forward-looking critical theory and practice to develop that engagement. It draws upon relatively new as well as established concepts, including the Capabilities Approach, to suggest how and why diversity management and social justice might be elevated to first-order constructs that inform leadership and its development. The evidence base is recent research for the Learning and Skills Sector, but the implications inform other parts of the education sector in which, as yet, approaches to diversity appear to have changed little. It is suggested that researchers, theorists and policy makers need to join with the education practitioner community to revitalize theory and practice.