Abstract: Massive retirements and an aging workforce create an urgent need for the development of future administrators to fill anticipated administrative vacancies in the community college system. My action research tests talent engagement in a large, urban, multi-college district. Through varied qualitative methods including the formation of a district-wide leadership task force, faculty focus group, interviews with ten promising faculty leaders and their reflective journal writing, this research captures the perceptions of administrators and faculty of the personal and organizational barriers and motivational factors for future administrative leadership development in a California Community College District. The Leadership Development Task Force is represented by experienced, mid-level managers. Six deans, each with a minimum of five years of experience, were selected from three colleges in a multi-college district to guide the talent development process. Each dean nominated two promising faculty for leadership preparation and mentored them through a leadership experience. Lessons learned from administrators and promising faculty leaders resulted in recommendations to the chancellor for future administrative training. The following questions guided my study: (1) What are the processes by which a community college leadership taskforce prepares faculty for leadership? (2) What barriers exist for faculty interested in administrative leadership roles? (3) What factors motivate faculty to consider administrative careers?