There has been sustained argument for contextualization of leadership development, none more so than when working with Indigenous and other marginalized peoples. Leadership development programmes are predominantly conducted by `outsider? educationalists and consultants and the question of contextualization, of how much or how little, is a decision that is ultimately made in classrooms around the world under conditions of alien tutelage. Employing an autoethnographic approach, the article examines three examples of leadership development programmes in order to think about generalization and/or contextualization. Overall, this study finds that arguments for and against `generalizability? and `contextualization? might depend more on the skill and experience of the teacher rather than the corpus of knowledge over which so many battles are fought. It suggests that the potential embedded in generalizable programmes can be realized if there is sufficient pedagogic engagement and space created by culturally competent teachers and facilitators for local testing of generalized knowledge claims for their adaptation: personally, organizationally, nationally and globally. It also finds that the people and outcome focus aspects of leadership development seem to be more influenced by culture than other aspects such as personal leadership style preference that would appear to transcend ethic cultural background.