Community colleges are experiencing a retirement crisis. The American Association of Community Colleges (AACC) and the Association of Community College Trustees (2018) reported that as many as half of community college presidents presiding in 2016 were likely to retire by 2021. Many current community college vice presidents are not interested in presidencies and are also retiring. Community colleges are the workhorses of higher education in the United States, and as such, the health of our nation depends on strong leaders to guide these institutions as they empower our citizenry by producing student learning. This dissertation examines the leadership pipeline from faculty to chair to dean to academic VP/CAO and seeks to propose new solutions to help ameliorate the retirement crisis. Through the use of Critical Interpretive Synthesis, scholarly literature was identified and analyzed. The results were interpreted through the lens of two theoretical constructs: Amey's (2005) Leadership as Learning and Quatro, Waldman, and Galvin's (2007) ACES Leadership Theory, as well as the leadership competency framework from the AACC (2013). The resulting interpretation and synthesis produced a model that can be used by individuals, community colleges, universities, and other organizations working to provide professional development for community college leaders. [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.]