This article emphasizes the extent to which conceptions of authenticity are forged through social interaction and socially mediated identities and how, in turn, authentic leadership involves the transformation of the organizational, social or cultural order in which leadership is situated. The overarching context for this exploration of authentic leadership is the loss of authentic meaning inherent in modern times and the importance of developing a fulfilled identity as a way of developing the possibility of meaning. An analytical distinction is made between three dimensions of authenticity (personal, ideal, social) before turning to the specific social context constituted by the contemporary modern era. This context--the enhancement of entrepreneurialism in public sector organisations which gives rise to bureau-enterprise culture--is outlined and, building on sociological work by the author, the nature of social authenticity and identities, and how they interlink with the other dimensions in this culture, are explored. The task for educational leadership concerned with authenticity is, it is proposed, to take a strategic approach to searching out and maximising the democratic potential within contemporary trends towards the bureau-enterprise culture. (Contains 4 figures and 2 notes.)