This executive dissertation assumes a sensemaking lens to investigate how Assistant and Associate Vice President (AVP)-level administrators in student affairs approach their supervisory roles within the current climate of higher education and employment. The study's primary goal is to identify how leaders can prepare for changing employment trends and transitions to facilitate and support positive outcomes and satisfaction within their departments and for their staff. The COVID-19 pandemic cast an unforgiving spotlight on longstanding issues within employment in the student affairs profession, which ruptured under the pressures of the outbreak, socio-political upheaval, and massive demographic shifts. Though turnover trends have plagued the student affairs profession for years, COVID-19 demonstrated the inability of traditional human resource practices to meet the changing needs of employees and institutions. This study addresses the following research questions: 1) how do AVP-level student affairs administrators make sense of employment data and trends to inform their supervisory practice? and 2) how do AVP-level student affairs administrators make sense of their role (relationship + actions) in supporting staff members beyond university-wide HR efforts? To answer these questions, this dissertation employed a qualitative approach using semi-structured interviews. The main results of the study identified five themes, including issues of recruitment, retention, and resignation; shifts in worker norms; considerations of the identity of a supervisor; changing workforce trends; and institutional priorities. These themes notably revolved around the need for AVPs to navigate various forms of tension. These findings have substantial implications for enhancing supervisory approaches to support positive outcomes for student affairs professionals, supporting recommendations for new pathways to the profession, and creating space for proactive versus reactive approaches to employment trends. Ultimately, the goal is to support increased satisfaction and retention in the field of student affairs. The findings contribute to research by addressing trends in an increasingly multigenerational workforce, supervisory approaches in student affairs, and strategies for navigating societal and demographic shifts. [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.]