This chapter explores the implications of the general challenges and transformation in the social sector for its leadership. It examines conceptually linking leadership challenges to different stages in the lifecycle of social organisations, distinguishing between social start-ups and established Non-profit institutions. The chapter relates leadership tasks to the process of organisational development as it is described in two popular models: The first is indicated in the Open Book of Social Innovation and differentiates between six steps from the initial idea to systemic change. The second model is based on the research of Friedrich Glasl and Bernard Lievegoed, who differentiate between four stages of the organisational lifecycle, i.e., the phases of pioneering, differentiation, integration, and association. Before the pioneering phase actually starts one person has to take the lead to formulate a social cause and be convinced about the solution approach. The journey of a social leader has lots of trade-offs.