This qualitative study presents an analysis of how guided visits to an art museum can provide leadership lessons for developing school leaders. The principal interns participated in teaching artists-facilitated guided arts engagement sessions at a large metropolitan museum. The sessions included art-making, observations of portraiture in the visual arts, discussions around their reactions to the art, and information on the artists' choices, processes, and techniques. Data sources included observations of the sessions and interviews with participants; these were analyzed using thematic analysis methods. Findings indicated that guided engagement with the visual arts provided insights to participants about self (intrapersonal learning), understanding about how others learn (interpersonal learning), and development of a sense of agency through creative self-expression and changes in practice. The art-making and related narratives participants generated served as analogical bridges transferring learning from the arts experience to their leadership practice. Some participants also provided feedback on how they took this learning and translated it into action in their schools.