Objective: This article focuses on wraparound as an example of a team planning process, and uses data from several sources to reflect on questions about whether—and under what conditions—collaborative teams are successful in engaging young people—and their caregivers—in planning. Methods: We used data collected in three studies to address our research questions. The first data set comes from a study on wraparound service planning in Nevada. We examined data collected from 23 matched pairs of caregivers and youth at 6 months after wrap-around planning began. Our second data set came from a national study of 41 local wraparound programs throughout the United States. Our analyses use data from 366 matched pairs of caregivers/youth. The third dataset comes from the pilot test of the Achieve My Plan! intervention. Data was gathered from eight teams before and after the intervention was implemented. Results: Taken together, the findings suggest that teams' success in managing caregiver and adolescent perspectives simultaneously during care and treatment planning is more strongly related to the quality of the team process than to youth age. Conclusions and Implications for Practice: Through attention to youth engagement, preparation, and team process, it appears possible to increase meaningful youth participation in planning without sacrificing caregiver satisfaction with the team experience.