This qualitative phenomenological study explored the personal insights, preferences, and experiences of individuals who graduated from a community leadership development program. Fifteen Bay Area Leadership Program graduates from the Burlington and Hamilton, Ontario, Canada program between 2002-2007 participated in this study. Several inter-related themes emerged from the respondents’ stories and narratives regarding the program elements that influenced the learning experience. Respondents’ acknowledged and recognized that the program had positively impacted their development as a community leader and the community. Through findings from extensive interviews of the graduates, the study: (1) extends current knowledge concerning the development of community leaders; (2) offers community program board members and management an understanding of key program elements that contribute to the learner’s experience; (3) extends evaluation approaches to the personal learning experience and developing theories of leadership to practice; and (4) provides an understanding of long-term program benefits in assisting future funding, supporting long-term sustainability of the community leadership development movement and ultimately strengthening communities.