This paper focuses on educational leadership in the context of social transition to post-apartheid democracy in South Africa. Transitional leaders manifest behaviours, attitudes, values and strategies that are deeply related to the contexts within which they work. Social norms and political climate may not be supportive of educational leaders wishing to rise to the challenge of unplanned transition; however this paper focuses on leaders who take up this challenge. Narratives of three educational leaders, two white and one black, provide an understanding of the complexities and challenges involved in bringing about change that goes against the grain of social, community, or institutional expectations. Five common strands that bind the narratives of the three leaders are revealed. These commonalities are: a sense of moral purpose, a sense of human frailty, a sense of racial inclusion, a sense of political complexity, and a sense of personal growth. In conclusion, seven propositions that may form the building blocks for new ways of thinking about leadership in post conflict societies are presented.