Young adults with disabilities face multiple challenges in obtaining successful post-school employment outcomes. This situation has remained relatively unchanged despite nearly 25 years of federal attention to the issue, including mandated transition services and a series of additional significant legislative responses. KentuckyWorks is a five-year systems change grant project designed to directly impact post-school outcomes for youth with intellectual and developmental disabilities in Kentucky. Among the approaches adopted to reach the KentuckyWorks project's goals is conducting a series of "community conversations". Community conversations are an asset-based approach for generating and informing efforts to improve employment outcomes for young people with disabilities. The statewide community conversation described in this article helped the KentuckyWorks team to identify steps that can be taken to a wider context within the state.