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This study focuses on a self-portrait activity, one element used to form co-mentoring circles in a K-12 principal/program administrator certification program. The activity is an auto-ethnography leader candidates write, then share within the co-mentoring circle. Co-mentoring circles have been developed, refined, and evaluated over the past eight years as safe, learning-filled spaces for aspiring educational leaders to discuss their work as interns and learn about leadership together. Circle formation elements include: group agreements, confidentiality, communication skills, giving/receiving feedback, reflective practice, trust, ongoing assessment of the circle’s work, and three activities: “hopes and concerns,” the “professional timeline,” and the “self-portrait.” Circle participants describe how the self-portrait activity enhances the development of the circle and circle members’ reported leadership lessons.