The United States labor force is currently undergoing a significant demographic transition, which warrants an examination of its implications on higher education institutions. Millennials have surpassed baby boomers as the largest adult generation (Fry, 2020). Consequently, higher education leaders will need to better understand and identify these emerging trends so that institutions can facilitate the transition of the millennial generation into leadership while avoiding the loss of institutional knowledge. Despite the increasing need for skilled professional administrators, there is little research on the millennial generation's outlook on career advancement and corresponding influential factors such as personal, environmental, and social cognitive factors, rendering it crucial to investigate how this shift will impact higher education institutions and the career advancement opportunities for millennial director-level administrators. The study utilized a phenomenological approach to explore the factors that facilitated career advancement for millennial director-level administrators. The findings identified eight major themes: (1) mentoring matters, (2) networking, (3) professional development is a must, (4) turnover supporting career advancement, (5) confidence regarding career advancement, (6) skill acquisition, (7) education is the silver bullet, and (8) changing institutions. The themes derived from the participants' experiences and narratives, provided a comprehensive description of each factor supporting career advancement for millennial director-level administrators. The study's findings offer valuable insights for higher education institutions seeking to support and prepare millennials for leadership roles while retaining institutional knowledge. Thus, this research contributes to the current literature on workforce demographics, career advancement, and higher education administration and adds to the sparse literature on the factors that support career advancement for millennial director-level administrators in public higher education. [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.]