In South Africa, until recently, mentoring has not been formalized as part of school leadership induction programmes or of leadership professional development. However, the South African government identified mentoring as a distinctive aspect of its pilot leadership development programme for school principals. This programme signalled a shift from "ad hoc" and informal mentoring to building mentorship into school leadership development programmes. However, there is still no clear understanding about what constitutes effective mentoring models and the significance of similarity and diversity in a mentoring relationship. In this paper I draw from two dissimilar datasets to explore mentoring from an identity (gender and race) perspective. Using similarity-attraction theory, the paper highlights the complexity of mentoring models and suggests that higher levels of dissimilarity in a mentoring relationship may lead to disadvantage. (Contains 2 tables and 1 note.)