The central theoretical argument of this paper is that educational leadership and organisational development and change in educational institutions in developing countries will not be effective unless school leaders are aware of the challenges posed by contextual factors that might have an impact on their professional activities. The article contributes to the discourse on educational leadership in developing countries by explicating three such sets of contextual forces that educational leadership ought to take into account: (1) the contours of the education system in which school leadership, organisational change and development occur; (2) societal and (3) international contexts. These forces are viewed through Cultural Historical Activity Theory as theoretical lens, and then illustrated with findings from an empirical study in a developing country. The article concludes with a strategic plan for exercising school leadership that takes contextual conditions into account.