There appears to be a paucity of research on mentoring senior leaders (Hobson & Sharp, 2005) and yet a growing interest in the development of leadership through experience (Abra "et al.," 2003; McCauley "et al.," 1998). This paper therefore presents and evaluates a case study of a pilot mentoring scheme and programme for Directors of Finance (DoFs) in the UK National Health Service. The paper reviews DoFs' leadership needs within the three broad categories of pragmatism, effectiveness and sustainability, and provides a case study detailing the pilot mentoring scheme and programme. Values and challenges posed by this initiative as a model for leadership development are considered, and lead to the identification of eight cross-cutting tensions connected to mentoring senior leaders. This analysis provides lessons for the ongoing initiative and indicates key learning about managing mentoring and mentoring senior leaders that it is hoped will be of value beyond the scope of this study.