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Imagination allows us to explore the unknown, transcend the limitations of present reality, and break free from the confines of the past by creating fictional scenarios that generate new insights about ourselves and the world. While fantasy serves to gratify frustrated unconscious needs, imagination seeks to know the unknown and transcend the constraints of reality and temporality. In supervision, imagination is essential, as the supervisor and supervisee reflect on past therapeutic events in which only the supervisee participated as the therapist. Through their imaginative engagement, they enliven the presented therapeutic interaction and uncover new meanings in their dialogue concerning the emotional needs and motivations of the patient and the therapist, as well as the development of the therapeutic process. The paper elaborates on how, by imagining therapeutic scenes from the therapist’s perspective, the supervisor can access the supervisee’s phenomenological perception. By imagining omitted details, the supervisor can better contextualize the therapeutic interaction, and by imagining the supervisee’s internal dialogues with an internal supervisor, the supervisor can assess clinical capacities and uncover new dimensions of the supervisee’s professional identity. A vignette from supervision illustrates how imagining details excluded from the therapeutic narrative can shape and enrich the supervisory process.