The idea that the Principal’s performance matters most in organisations such as schools in terms of learning outcomes, has become dogma in contemporary leadership research. A central characteristic of such leader-centric views is that leaders are assumed to have cognitive autonomy (‘leader knows best’), and are accorded a conception of agency, the ‘self-as-controller’, based on traditional understandings of ‘self’. Emphasizing the self, as expressed in the injunction ‘to know oneself’, is a particular and influential variation of a leader-centric perspective, advocated by Avolio and Gardner (2005). ‘Knowing oneself’ is believed to be ‘the root construct’ that underlies all forms of positive leadership and its development and is labelled ‘authentic leadership development’. In this paper, I want to examine the notion of ‘self’ that underlies claims to authentic leadership and ask what ‘being authentic’ might mean for social-biological beings with evolved brains such as ours. Of particular importance is the relationship between ‘self’ and ‘context’, as for example anticipated by Mead and Goffman, and how this interrelationship might be construed through contemporary accounts of cognition. Just as the nature of human cognition is ‘social’ and constitutes a dynamic system with non biological components, so is the ‘self’. The ‘self’ can be understood as a system of multilevel interacting mechanisms (Thagard, 2014) that holds promise for explaining a range of human phenomena such as agency and autonomy. The fundamental point is that the ‘self’ is a natural but highly complex entity explicable by the means of cognitive science.The initial naturalistic exploration of the concept of ‘self’, so fundamental to leader-centric accounts, especially ‘authentic’ leadership, expands further the discussion of how better to understand how organisations such as schools function, that is as cognitive ecologies.