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The paper presents findings from a study that examined the preparation and development of school principals in four Southern African countries. The aim of the study was to examine processes and practices of leadership socialisation and leadership identity development. Previous research established a gap in the knowledge leading to poor theorisation of leadership development models, particularly in the developing context. The study therefore analysed processes, practices, and experiences that shape and inform leadership preparation and development in order to understand how broad leadership socialisation happens and how leadership identity develops with a view to identifying leadership development models that are informed by context. The findings show a strong relationship between context and the individual that ultimately shape the identity of a leader. The paper will argue that while it may be difficult to develop policy based on personal and individual school experiences, leadership development initiatives should be informed by contextual realities taking into account the personal, social and professional circumstances that shape experiences of school leaders.