In one's professional journey, the supervisor is key to the growth and development of the team as a whole and individual staff members. The ability of the supervisor to build relationships, provide ongoing training, and give critical and timely feedback is tantamount to that staff member's skill development, overall experience, and ultimately success in the role. For graduate assistants, particularly those in the field of student affairs, where attrition levels are often high, this supervisory relationship is vital. This research study focused on the role supervision played in the professional development of graduate assistants in student affairs, particularly in residence life. Specifically, this qualitative case study explored how graduate students experienced supervision while working in their residence life assistantships. Further, this study examined these supervisory relationships as a factor of attrition in residence life. Qualitative data was collected through interviews with seven recent graduates from higher education and student affairs master's programs. Participants had 0-5 years of professional experience working in their chosen field since earning their masters' degree while serving as residence life graduate assistants at universities in the mid-Atlantic and Northeast regions of the United States. Additionally, The researcher invited participants to share artifacts from their experiences, including expectations and evaluations received. This study is essential to the practice of student affairs professionals as it may provide insight into the supervisory practice and skill development of current and future professionals. This study may also guide professionals to improve the quality of supervision provided to graduate assistants during this crucial phase of their career development, which, in turn, may lead to lower attrition rates. The literature review conducted included an examination of residence life assistantships; factors surrounding the development of supervisory relationships; supervision practices, including socialization and orientation; and supervision theories. The themes and patterns discovered through the literature were applied to the research questions to determine the relationship between the initial perceptions and provide recommendations on improving supervisory practices to enhance the experience of graduate students in residence life and lower attrition rates. [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.]