Professionals within the field of student affairs administration provide essential support services to students within American higher education. As a profession, it is important to understand the way in which new student affairs professionals are socialized, supervised, and prepared for the demands of student support work. This arts-based, phenomenological study sought to understand the experiences of entry-level student affairs professionals and their supervisors within the context of supervisory relationships. Data were collected through an arts-based visual representation exercise, semi-structured interviews, and a researcher reflexive journal. Participants described the importance of strong foundational relationships between supervisors and supervisees, as well as challenges faced when supervisory relationships are not positive. Participants discussed shared experiences within the field of student affairs, including perceptions of high workload and inadequate pay, and the significant impact of perceived negative supervision experiences. Participants also shared the importance and influence of social identity on supervision relationships and overall professional experiences within the field. The results suggest a need for more consistent, formalized training on supervision skill development. The results also support recommendations that institutions endeavor to address systemic issues related to pay and workload, as well as increase efforts related to diversity, equity, and inclusion for employees. [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://www.proquest.com/en-US/products/dissertations/individuals.shtml.]