This chapter reviews leadership development in South Africa and the methods that are currently used to develop emerging leaders. I take a broad look at leadership development in a dynamic, changing, unpredictable postmodern era, together with that which needs to be preserved from the South African perspective in a dualistic environment of Afrocentric and Eurocentric leadership. I then illuminate some local examples and approaches to leadership development and make recommendations that reflect contemporary leadership development in South Africa, with all its diverse and complex socioeconomic contexts, peoples and social systems. The chapter illustrates examples of successful implementation of leadership development models and shows how they have succeeded amidst, and in spite of, numerous contextual challenges.