A growing body of research has investigated the virtues and complexities of mentoring in sports coaching. Yet, a paucity of research exists to consider 'how' both mentors and mentees come to understand their respective role(s). Attempting to redress this gap in research, the aim of this project was to examine the developmental experiences of mentors (and mentees) while participating in a mentoring programme within a University undergraduate sport coaching module. In doing so, this study specifically attended to the critical experiences of mentors and mentees in order to determine how, over the course of the module, mentors and mentees were able to operationalise their role within the coaching context. Data were collected through a series of focus group interviews with 10 mentors and 12 mentees, which were repeated over multiple time-points throughout the mentoring programme. The data were subject to a reflexive thematic analysis to yield three interrelated themes; initiating meaningful mentoring; the relationality of mentoring; and finally, putting 'mentoring' to work. The findings demonstrated the ability (and inability) of learners to develop the reflexive awareness required to negotiate and align their identities within the pedagogical context under study. Drawing upon the explanatory work of Goffman and Crossley, the study contributes to the deconstruction of mentoring practice more specifically, and the wider understanding of complexity of socialisation in coaching and education more generally.