Inequality in educational attainment is a serious and increasing problem in Scotland and the rest of the United Kingdom, and youth mentoring is gaining popularity as an intervention to address this issue. However, evidence for the effectiveness of mentoring is weak, and research suggests that a large proportion of mentoring relationships end prematurely, which can be harmful to young people. This article draws on data from the Glasgow Intergenerational Mentoring Network, an ongoing research and development project facilitating mentoring for secondary school pupils in socially disadvantaged areas, employing retired professionals as volunteer mentors. Case material is presented to discuss the nature of mentoring and the role of the mentor. This article conceptualizes volunteer mentors as relational experts, relational learners, and nonrelational mentors. The implications of these categories are discussed in terms of recruitment, training, and support of mentors, to facilitate ethical and effective mentoring relationships.