This dissertation reports on an exploration of school leadership from the perspective of how school leaders bring multiple cognitive interests to bear in their leadership practice. By analysing the discourse of practising school leaders this study has enabled insight to be gained into school leaders’ reflections-on-actions in given leadership situations. On the basis of the analysis of discourse it is concluded in this study that school based leadership, and school leadership preparation, can be enhanced when illuminated through a cognitive perspective grounded in Habermas’ theory of knowledge-constitutive interests (1971). Recommendations are given in this dissertation for the development of an approach to school leadership preparation built on a cognitive interests framework. Based in qualitative research techniques the main evidentiary material was elicited by the use of semi-structured interviews, and the collection of narratives, and was analysed with a variation of Membership Categorisation Analysis (Sacks, 1972).