Kerry and Murdoch (1993), analysing the essential characteristics of leaders and school principals, raised two key questions: (1) What kind of leadership will schools require to help them face the next ten years?; and (2) How equipped are managers in school to provide that leadership? Traditionally, aspiring school principals emerge from the profession by developing the necessary organisational and leadership skills contextually. It is expected that they will already possess a secure and deep understanding of the educational focus of the role and will have been developing and practising the managerial and leadership aspects as they progressed through the management hierarchy. The work of Schneider (2004) offers the possibility of an alternative route to school leadership. Working with retired military officers in Israel, Schneider has developed a programme to "fast-track" potential candidates to the role of school principals. In this article, the authors compare the training and development needs of a group of retired military officers aspiring to principalship with those of experienced teachers with the same aims. Using Campbell's (1999) criteria: leadership, organizational management and professionalism (as presented in their understanding of relevant pedagogy), the qualities, existing and potential capabilities of the two groups were analysed.