Instructors of 3D design workshops for children face many challenges, including maintaining awareness of students’ progress, helping students who need additional attention, and creating a fun experience while still achieving learning goals. To help address these challenges, we developed Maestro, a workshop orchestration system that visualizes students’ progress, automatically detects and draws attention to common challenges faced by students, and provides mechanisms to address common student challenges as they occur. We present the design of Maestro, and the results of a case-study evaluation with an experienced facilitator and 13 children. The facilitator appreciated Maestro’s real-time indications of which students were successfully following her tutorial demonstration, and recognized the system’s potential to “extend her reach” while helping struggling students. Participant interaction data from the study provided support for our follow-along detection algorithm, and the capability to remind students to use 3D navigation.