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Focusing on creating developmental mentoring relationships for future educational leaders, this paper reports the findings from the use of an auto-ethnographic approach called the self-portrait. After sharing the written self-portrait with the university-based mentor, the leader candidate (intern) has the option of discussing her/his self-portrait among the intern cohort. The decision to discuss one’s self-portrait is often the first step in creating trusting developmental relationships, since the self-portrait discussions are deeply personal and self-revealing. As deepened trusting, developmental relationships have formed, a co-mentoring community has begun to develop among those who share their self-portraits with each other. The self-portrait process offers a new approach to mentors seeking to develop or deepen developmental relationships with those they mentor.