This article reports of a study of workplace supervision and student experiences and outcomes through insights from semi-structured interviews with 21 graduates who had previously supervised work placement students. The study focused on questions framed from the perspective of the interviewees’ work placement experiences as a student and then as a supervisor (e.g., impact, motivation, insights for future students/supervisors, and graduate attributes). The findings from this study indicate importance of workplace supervisors setting expectations and engaging in initial planning and organizing for effective management of the work placement. Findings also suggest that the supervising can usefully take the form of mentoring, and that this provides the supervisor with professional development in self-management, effective communication and leadership. Implications for future WIL practice include utilizing workplace supervisors, particularly those who are themselves WIL graduates, to help further enhance student WIL experiences, learning outcomes, and legacies