Evaluating aesthetic-artistic actions in production, reception, and reflection demands both the sensitization and differentiation of perceptual abilities and an adequate realization and articulation of aesthetic impressions and attitudes. This article demonstrates how a multidimensional engagement with and shared reflection upon original works can support aesthetic judgment in this context, and which different (communicative) processes contribute to this. Research materials from the vignette research project “Nah am Werk” form the basis for the discussion, in which phenomenological vignettes, analogous to works of art, are conceived as an instrument for sensitizing perception, reflection, and judgment. The aim is to equip (trainee) teachers with the attention, listening skills, and empathy that they in particular require in recognizing, supporting, and evaluating the aesthetic potential of their students.