Is a capability to engage students as fundamental to effective museum education as a working knowledge of the collections? What strategies can raise the level of engagement with students and sustain student engagement with works of art? What are the challenges that older students on school tours present to docents? This article highlights discussions with docents during and after a professional development session. It identifies specific student engagement behaviors that challenge museum educators' self-efficacy and offers insight on developing new engagement skills. A university art educator collaborated with the director of education at the McNay Art Museum for this investigation.