The amount of empirical research on leadership of educational organisations, and especially of schools, which has stressed the importance of being sensitive to context, is not great. This paper seeks to highlight the challenge presented by this situation. First, context is defined. Second, attention is drawn to what can be learned in the area of school leadership from the emphasis in other bodies of scholarship within the broad field of education studies on paying attention to matters of context. Third, an overview is provided of some of the key considerations arising out of the small body of work undertaken in the field by those researchers who have focussed on the broad range of issues that can arise for school leaders in distinctive contexts. Finally, five key and interconnected propositions to guide practice with regard to leadership in diverse contexts that have been generated from an analysis of the latter body of work are presented. In doing so, it is recognised that these are tentative in the absence of a much larger corpus of work. Overall, we hope that, along with providing intellectual sustenance, each of the four areas considered will also stimulate discussion on areas for further research.