Although early work experiences can impart a number of benefits to adolescents with disabilities, few students have meaningful access to these opportunities. The authors examined "community conversations" to build capacity and interest in expanding employment opportunities. Events were held in seven different communities and used the World Cafe process (Brown & Isaacs, 2005) to facilitate asset-based identification of localized next steps. Observations, analyses of surveys completed by the 239 community members who attended, and examination of artifacts suggested that the events offer a promising avenue for identifying solutions, building social capital, and increasing employment opportunities. The authors offer recommendations for drawing on this approach to harness and build the capacity of communities to support youth in transition, along with directions for future research. (Contains 3 tables.)