Jazz musicians are unique individuals who seek to perform from a transcendental state in which tacit knowledge, teamwork, and communication blend to produce an effective performance. Academic leaders are also unique individuals who rely on communication to generate a sense of inclusion within a complex organization that at times epitomizes anarchy. The purpose of this Interpretive Phenomenological Analysis (IPA) is to examine the relationship between the skills and perspectives of improvising jazz musicians and academic leaders. Jazz musicians with experience as academic leaders shared their experiences in digitally recorded, semi structured interviews. The transcripts were analyzed to discover whether there was a relationship between the participant's experiences as jazz musicians and academic leaders. IPA was used as a qualitative analysis method to generate a hierarchy of themes that were integrated to form a composite picture of the phenomenon. The intent of the study was to discover whether jazz improvisation or its constituent elements could inform academic leadership. The phenomenon under examination was how jazz musicians experienced academic leadership. The essence of the participant's experiences has implications for leadership, higher education, and jazz musicians. An understanding of the shared experience could inform how jazz musicians, academic leaders, and leaders in other environments view their interpersonal interactions. Utilizing the practice of improvising jazz musicians may provide a unique perspective for leaders in any complex environment. Envisioning leadership through the lens of a jazz musician may provide an innovative approach that can benefit a diverse audience. [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.]