The experiences youth with disabilities have during middle and high school can dramatically change their trajectories into adulthood. Students who access strong vocational instruction, accrue early work experience, and aspire toward a future career are much more likely to achieve their employment goals in the early years after high school. As educators and professionals, how can we best prepare and position our students for the world of work? This presentation will address promising practices for schools committed to elevating employment outcomes for youth with disabilities—both during the school year and in the summer months. It will emphasize the importance of high expectations, thoughtful planning, family engagement, agency involvement, and community partnerships, as well as illustrate the ways in which schools can implement these critical components locally. Particular attention will be given to the contributions “community conversations” can make toward developing strong partnerships within and beyond the disability service system.