Mentoring provides a relational intervention that can promote positive youth development among adolescents who are involved in the juvenile justice system. The perspectives of mentors engaging these youth, particularly insights considered through a cultural humility lens, have been largely absent from the literature to date. This study examined predominately White, middle‐ to upper‐class adult mentors’ experiences mentoring racially diverse, working‐class youth. Semi‐structured qualitative interviews were completed with 23 mentors participating in a community‐based mentoring program. Themes were derived from inductive content analysis. Emergent themes illustrative of the mentoring process included (a) establishing a connection despite differences, (b) identifying mentees’ personal and environmental challenges, and (c) raising consciousness around structural issues. Despite coming from different backgrounds and experiences, mentors who worked with justice‐involved adolescents were motivated to connect with their mentees. Mentors developed a greater awareness of structural challenges influencing adolescents by learning about the multifaceted experiences and needs of their mentees.