Mentoring as a means of supporting young people perceived as having difficulties or being at risk of disaffection has become an important feature of pastoral support approaches in and around schools in recent years. The provision of support that is based upon a highly personalised relationship and founded upon principles of unconditional positive regard has been a feature of many schools and has been endorsed at government and local authority levels. Drawing upon two recently conducted research projects, this paper considers the motivations of mentors, the definition and development of the mentoring role and the ways in which it is being developed in respect of young people. The authors suggest that a certain ambiguity and fluidity of definition of the role of the mentor may be a strength rather than a weakness when developing supportive pastoral systems. The paper considers the motivations of mentors and how these may impact upon the success of mentoring schemes. (Contains 1 figure.)