This study examined how midlevel leaders in Student Affairs make meaning of their supervision practice. Semistructured interviews were conducted with seven midlevel supervisors throughout various higher education institutions in the United States. Transcripts were analyzed using interpretative phenomenological analysis to identify themes. Four superordinate themes emerged: "Experience itself was a clear factor in how supervision was learned; There are challenges inherent to navigating the nuances between management and leadership within supervision; Leader and staff member identity development affects the supervision experience," and "Leader and staff member emotional intelligence affects the supervision experience." Knowledge generated from this analysis can inform supervision practice by enabling supervisors to strategically consider the various systems that influence their leadership approaches, thereby enhancing their ability to adapt to complex organizational dynamics. This, in turn, provides opportunities for more effective, context-sensitive leadership across the field, fostering innovation and systemic improvements in supervisory practices. [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.]