This paper explores the lived experience of leadership development within an individual organisation as seen from the perspective of four directors of a major organization. There is a dearth of research exploring the lived experience of leadership at the level of the individual, particularly focused at informal naturalistic development (Burgoyne & Hodgson, 1985). Further there has been a call for qualitative research into leadership development (Day, 2000; Lowe & Gardener, 2001) and it is towards such a methodology that this research seeks to contribute. Qualitative research in the form of in-depth purposive interviews have been undertaken with four directors of an Multi-national Public Limited Company who were asked to explore how they have learnt how to lead. Grounded theory (Parry, 1998) has been utilized to identify key themes drawn from transcribed interviews.