This qualitative study explored how supervisors in student affairs describe their supervisory learning journey. Supervision is an important facet of the student affairs profession, yet there is an apparent lack of intentional supervisory training and development for these professionals. This study endeavored to understand how supervisors in student affairs learn to supervise and how their previous supervisors influenced their learning journey. Guided by a conceptual framework that integrated reflective and emotional aspects of experiential learning theories, this study employed generic qualitative methods to address two primary research questions. The sample featured 11 supervisors in student affairs from a myriad of institutions across the United States representing a various functional areas of student affairs. Multiple interviews and reflective writing activities were conducted with participants during the summer of 2023. Analysis of the data indicated that participants' learning of supervision was highly influenced by their previous supervisors, and that, overall, supervisory learning was a subjective, irregular, and informal process. Moreover, participants revealed that supervisory learning was a lifelong endeavor involving emotional and reflective responses to experiences. The findings in tandem with the conceptual framework led to a proposed model for emotional-reflective professional learning, which can be used to better understand how experience, emotions, and reflection intersect to help professionals make meaning and inform their practice. This dissertation concluded with implications for research and practice as well as recommendations 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.]