Strong leadership capabilities are essential for effective health services, yet definitions of leadership remain contested. Despite the acknowledged contextual specificity of leadership styles, most leadership theories draw heavily from Western conceptualizations. This cultural bias may attenuate the effectiveness of programmes intended to transform healthcare practice in Sub-Saharan Africa, where few empirical studies on health leadership have been conducted. This paper examines how effective leadership by doctors was perceived by stakeholders in one particular context, Sierra Leone. Drawing together extensive experience of in-country healthcare provision with a series of in-depth interviews with 27 Sierra Leonean doctors, we extended a grounded-theory approach to come to grips with the reach and relevance of contemporary leadership models in capturing the local experiences and relevance of leadership. We found that participants conceptualized leadership according to established leadership models, such as transformational and relational theories. However, participants also pointed to distinctive challenges attendant to healthcare provision in Sierra Leone that required specific leadership capabilities. Context-specific factors included health system breakdown, politicization in the health sector and lack of accountability, placing importance on skills such as persistence, role modelling and taking initiative. Participants also described pressure to behave in ways they deemed antithetical to their personal and professional values and also necessary in order to continue a career in the public sector. The challenge of navigating such ethical dilemmas was a defining feature of leadership in Sierra Leone. Our research demonstrates that while international leadership models were relevant in this context, there is strong emphasis on contingent or situational leadership theories. We further contribute to policy and practice by informing design of leadership development programmes and the establishment of a more enabling environment for medical leadership by governments and international donors.