This study examines the Mary Reynolds Babcock Foundation’s (MRBF) Southern Grassroots Leadership Development Learning Program through which 17 grassroots organizations received support between 1998 and 2002. Support for the engagement and cultivation of grassroots leaders lies at the very heart of the MRBF’s mission to help build “just and caring communities” in the Southeastern United States. It has helped organizations dedicated to community improvement identify community priorities, develop effective strategies to address them, and hold themselves accountable to the communities in which they work. The MRBF Learning Program provided practitioners in these organizations with the opportunity to step back, reflect, and become more intentional about enhancing grassroots leadership development within their organizations and communities. This paper captures lessons about using a learning initiative to enhance the impact of leadership development efforts. It describes the Learning Program and its outcomes for an audience of foundations, intermediaries, nonprofits, and others interested in supporting, managing, or participating in a learning initiative. It identifies some of the factors that contribute to the success of such initiatives. The paper also addresses key design questions that are likely to be important to any learning initiative.