Supervisors of on-campus student employees are perhaps the most consistent touchpoint of a working undergraduate's college experience and the criticality of this role within higher education has gone relatively unrecognized. The current study explored how student affairs professionals learn to supervise student employees who work part-time on campus in co-curricular settings. This qualitative investigation of 11 student affairs professionals sought to learn what supervisors of student employees perceive to be the responsibilities of their role and how they learned to supervise on-campus student employees. Using Role Identity Theory to frame this research, the findings revealed that the participants felt they embodied a plethora of idiosyncratic identities in their role as a supervisor of student employees. Participants experienced a range of emotions associated with their extensive scope of responsibility. Their perceived responsibilities were vast in nature and in stark contrast to what they felt was expected of them from their supervisors' and institutions' points of view. The findings demonstrated that participants taught themselves how to supervise in the absence of supervisory coursework in their educational programs and institutions' human resources trainings. The data also revealed unexpected findings, such as the supervisory challenges presented by current events and students' motivation to work. Additionally, the participants' experiences put a spotlight on the impact of student employment on institutions of higher education. This study provides extensive recommendations for practice and areas of future research. To reap the institutional rewards of on-campus student employment programs, colleges and universities must invest in the supervisors who are responsible for these students. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]