In this chapter we present key insights gleaned from case study research conducted in two very different secondary schools. Through the stories of “Carol”, the principal of a secondary school in an urban area in Australia and “Jenny”, the head teacher of a secondary school in outer London, we examine some of the challenges associated with pursuing socially just leadership. We locate such challenges within a broader socio-political environment of unprecedented diversity where schools must respond to new equity questions and ascribe to the ever-demanding expectations of audit and accountability that narrow their priorities. The chapter draws on Michel Foucault’s key work around ethics to explore and provide critical insight into how school leaders might work in more socially just ways. In understanding the complexities confronting school leaders, we find particular utility in Foucault’s ideas of advocacy, truth-telling and counter-conduct. It is our contention that they capture the processes that work towards social justice through leadership that moves beyond a narrow performative focus to removing the barriers and structures (whether they be economic, cultural or political) that constrain students’ lives and their capacity to participate in the social world on par with others.