How can we teach inter-organizational collaboration? Reflecting on series of experimental library and information science courses taught from 2011-2015, the Youth Services Community Engagement courses grew out of an IMLS-funded grant focused on innovative services to youth. The course required service-learning experiences in organizations other than libraries; preparing students for effective youth advocacy through inter-organizational collaboration emerged as a learning outcome. Reflections on the iterative design of this service-learning approach working between libraries and community organizations explore how student input influenced course development, including learning outcomes. This reflection highlights the need for more research in library and information science (LIS) on connections and disconnections between public libraries and community organizations.