Leadership has long been unhelpfully constructed as masculine. Nevertheless, little research uses gender and feminist theory to analyse dominant leadership discourses and their enactment by men headteachers. Here, the conceptual tools of monoglossia, heteroglossia and polyglossia uncover nuances in a headteacher’s discursive struggles in his leadership for social justice. Gender theory illuminates his compliance with and transgression of masculinist hegemonic leadership in the negotiation of a discourse of values and the discourse of performativity that pervades educational leadership in neoliberal times. His conflation of incompatible discourses will interest readers wondering how headteachers make sense of their work.