The purpose of this study was to explore how midlevel managers in student affairs learn supervisory skills. Student affairs professionals are given tremendous responsibility for the lives of students outside the classroom. The Association of College Personnel Administrators and other sources outlined the necessary competencies for student affairs professionals to be successful in the field and found supervision to be an important skill for all levels of the profession. Midlevel managers assume many management responsibilities, but there is a dearth of literature surrounding midlevel managers and their responsibilities. This was a basic qualitative study that examined how midlevel managers learned supervisory skills. Midlevel managers reflected on their personal journeys of learning supervisory skills. The sample featured 20 midlevel student affairs professionals from various institutions across the country who were interviewed in the summer of 2009. Transcripts were analyzed using the constant comparative method. Analysis revealed that the nature of learning was informal and involved self-directed learning and experiential learning. Next, there was a process of learning supervisory skills, which included (a) entry into the field, (b) realization of becoming a supervisor, (c) seeking resources, and (d) implementation of learning strategies. Contextual factors that influenced the process of learning supervisory skills included barriers and a continuous learning process. The results also illustrated the connection between supervision and professionalism. The dissertation concludes with implications for the field, recommendations focused on the student affairs profession, and suggestions for future research. [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.]