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How does one’s personal history influence professional practice as a supervisor? This study demonstrates the significance that personal experiences can have for role-related self-reflection and, consequently, for professional practice. Drawing on theoretical perspectives on supervision, role, psychoanalysis and transactional analysis, personal history and reflection, the study examines three narrative interviews with experienced supervisors. Using Schütze’s narrative analysis, personal experiences and their significance for the professional role are identified and examined through a comparative case study approach. This work is aimed at anyone interested in professional self-reflection and the connection between personal history and professional role.