Strong collaborations are critical to successful youth transitions. Preparing students with disabilities for life after high school requires extensive partnerships within and beyond the school. However, transition educators often struggle to meaningfully engage the people and programs that exist within their local community. A community conversation event is a practical, fun, and effective way for districts to capture fresh perspectives and identify innovative, local solutions to persistent challenges in transition education. The purpose of this article is to highlight the key steps for planning for a community conversation, implementing the event, and using information gathered to inform improvements to transition programming. We draw from our work supporting 10 Tennessee school districts who hosted their own community conversations to reflect upon and improve their transition practices. We provide resources, materials, and tips for school districts to implement a successful event that leads to improvements in transition programming and student outcomes.