Although preparing youth with significant disabilities for future careers is a central focus of transition education, the task can be overwhelming for high school teachers and staff to tackle alone. Educators describe a number of common barriers to promoting youth employment, including the perceived inexperience of the student, the unwillingness of local employers to hire youth with disabilities, limited awareness by teachers and families of the array of work-related opportunities and resources that might exist in their communities, weak linkages between schools and community employers, and difficulty finding transportation and on-the-job supports. The broader community needs to be more meaningfully and effectively engaged to substantively improve outcomes for youth with significant disabilities. Communities are reservoirs of expertise, relationships, supports, opportunities, ideas, and other assets that can be used to expand the employment experiences of youth with disabilities. This article discusses a research project which focused on developing effective, practical strategies that schools and communities can use to expand employment opportunities and outcomes for transition-age youth with significant disabilities. Recognizing the importance of the receptiveness and support of the local community, the project team worked with seven diverse communities to explore “community conversations” as a launching point for efforts to expand local employment for youth with significant disabilities. These conversations were designed to: (1) foster dialogue centered on ways that schools, businesses, agencies, organizations, families, youth, and others could work together to broaden the job opportunities in their local community; and (2) identify new partners willing to collaborate with participating high schools in addressing youth employment. The article outlines the practical steps and considerations associated with implementing a community conversation, and describes the promise this strategy holds for improving the transition experiences of youth with disabilities.