Despite the current press to improve school leadership, little scholarly attention focuses on building problem-solving skills in university leadership preparation programmes. This paper reports on two qualitative case studies that examined educational leadership students' probing of school problems through the arts. Fieldwork was used to derive inductive explanations of minimally documented leadership experience (grounded theory) and understanding human development through producing and/or participating in works of art (arts-based inquiry). Data sources included videos and participant observations of improvisational theatre role-plays; observations of making pottery, drawing and three-dimensional metaphors; interviews; and extant documents including student journals, web-based discussions and course evaluations. Study #1 found that educational leadership students reflected on personal and professional fears, engaged in creative risks and returned to creative roots. In study #2, six phases of problem-solving through improvisational theatre role-playing emerged: selecting, projecting, amplifying the problem, deriving tentative solutions, objectifying the problem and selecting a better solution to the problem. Comparison of these findings suggests two distinct approaches to solving problems: 'problem framing' (study #1) versus 'problem solving' (study #2). This distinction lends insight into the cognitive and affective aspects of learning through the arts for educational leadership students, and how faculty can help these students to navigate and facilitate this learning process.