Community college enrollment has seen a significant shift in student demographics, including the decline of White students from 60% in 2001 to 46.2% in 2017 (American Association of Community Colleges, 2019), whereas efforts to diversify senior leadership have had little success (Rodriguez, 2015). Examining literature from peer-reviewed journals, public scholarships, and conversations with practitioners led to the emergence of the following four reasons for this problem: limited pipeline of qualified individuals of color, lack of support that benefits the professional development of people of color (POC), unconscious bias within screening committees, and the existence of structural racism. To address the leadership pipeline and lack of support for the professional development of POC, a literature review pertinent to the best practices of leadership academies or "Grow Your Own" (GYO) leadership programs was conducted. The analysis, which included peer-reviewed journals, public scholarship, and conversations with practitioners, led to the emergence of five best practices: recruitment strategies, networking opportunities, involvement and support of the college president and other senior leaders, experiential learning opportunities, and reflection opportunities. Further, a mixed-method developmental program evaluation approach with an experimental design was leveraged to answer the following four program evaluation questions: (1) To what extent does messaging that focuses on personal gains versus collective or organizational benefits impact the potential enrollment in a leadership academy? How does this vary by race and gender? (2) What message content resonates with prospective participants? (3) What type of recruitment efforts are most likely to lead POC to participate in a leadership academy? (4) Who from the organization should be involved in the recruitment for a leadership academy? How should they be involved and why? The results provided information about messaging for leadership academies with various intersections with race and gender and the importance of using diversity, equity, and inclusion-related language in the recruitment messages. [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.]