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Leadership is basically about influence and ability to cultivate followership. This chapter examined the nature of indigenous socio-political leadership in Africa using Zimbabwe, Sudan and Nigeria as caselets and compared this with the post-colonial or modern-day leadership realities. A survey was conducted among senior executives at Lagos Business School, Nigeria, with a sample size of 200 persons, to find out their perception of the African indigenous leadership system. An overwhelming 90% believe that culture plays a big role in shaping African leadership style. However, two-thirds of the respondents agreed that Africa lacks proper institutional structures to support good leadership, thus encouraging corruption (97% of the respondents) and non-accountability among the leaders. Also, only 5% thought cultural orientation was the reason why the African followers do not hold their leaders accountable. In other words, it is not in the African culture not to hold leaders accountable for their actions. So, what went wrong? We attempted a deeper look at the effect of colonial rule and the attendant militarisation of the African continent. Our conclusion is that the colonisation of the continent by Europe brought significant distortion to the traditional African indigenous leadership institutions and the psyche of the African leader and the followers alike. Post-colonial Africa has witnessed 133 recorded coups d’etat between 1952 and 2016. This chapter is recommended to all those who seek a deeper understanding of the nature of the African indigenous leadership practices and the factors that have shaped these over the years.