Docents--volunteer adult educators in art museums--adapt their tour content and process to best suit their audiences. This interpretive qualitative study explores the strategies docents used in four art museums in the Northeastern United States to tailor their educational activities and attempt to make them more relevant and interactive. Findings show strategies include assessing tour-goers' place of residence, prior knowledge of art, reasons for attendance, and observations of their gestures in order to make art and the visit relevant. Findings also show, however, that docents inadvertently perpetuate stereotypes of museum visitors; assessing one's audience is indeed nuanced and very complex. The results present challenges to museums to not only engage in the further education of their docents, but understand how their educational work can thwart efforts to overcome stereotyping of audiences.