Youth mentoring is often used to engage increasing numbers of disaffected and marginalised young people. As such, this research explores the extent to which key workers, across a range professional settings, adopt and integrate mentoring practices into their primary role. The research suggests that key workers recognise an informal and caring dimension to their primary role and use the term mentoring to capture the diversity of this activity. However, the attempt to facilitate integration into mainstream values and norms suggests that key workers and youngsters are actually engaged in a form of social pedagogy; undertaking social action to promote the personal development and general wellbeing of the youngster. As a piece of qualitative action research – based primarily on semi-structured interviews with key workers and young people – this inquiry also explores the extent to which practitioner mentoring, or social pedagogy, is successful as a transformation strategy – that is, the extent to which young people alter their attitudes, behaviours and beliefs as a result of being supported in this manner. The findings suggest that the informality of the interactions, a shared activity, the strength of the relationships and the duration of contact, are important aspects of social pedagogy/youth mentoring. The research has clear implications for practitioners, since the development of a ‘pedagogic perspective’ introduces a body of social theory into work previously undertaken intuitively. This, in turn, requires practitioners across professional settings to; engage with ‘clients’ on an a personal level to build trust and rapport, develop pedagogic opportunities that facilitate access to mainstream activities and, finally, maintain meaningful relationships until social inclusion is secure.