This dissertation investigates managerial leadership and its cultural foundations in Kenya. It discusses the theoretical underpinnings of culturally contingent leadership theories, and examines Sub-Saharan African leadership through existing literature, cultural metaphors, and qualitative and quantitative methodologies. The study replicates the Global Leadership and Organisational Behaviour Effectiveness (GLOBE) methodologies with 267 respondents – managers in the finance and food processing sectors, and the civic sector (education and health). The literature review focuses on leadership issues impeding socio-economic development, complexities such as ethnic heterogeneity, colonial history, customary practices, instability in governance, conflict, corruption, and poverty. The cultural domain is also examined in terms of ethno-linguistic groups and major historical and geo-political influences on these groups. Additional aspects of culture that pose persistent problems to Kenyan leadership are explored: paternalism and patronage, and the legacy of entitlement and bureaucracy –– negative influences on workrelated relations, and managerial and political leadership. Findings on organisational culture and societal culture indicate that Kenyan values and practices are not congruent, thereby creating a unique profile of Kenyan leader attributes and leadership styles. The study identifies Bwana Kubwa (Big Boss) managerial leadership as a norm, political leadership as “a dirty game,” and an “inspirational idealist” as the preferred leader. Lastly, survey results for Kenya are compared against GLOBE dimensions of culture and leadership for Sub-Saharan Africa, as well as against West Africa. / Communication Science / D. Litt. et Phil. (Communication Science)