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Focusing on creating developmental mentoring relationships for aspiring school leaders, this paper reports: the processes and practices used in establishing a co-mentoring circle, the participants’ reported effectiveness of the circle, and topics discussed. Co-mentoring circle is used to denote the small size of the group, generally 10 or fewer participants, as well as the reciprocal nature of the mentoring work done together. The co-mentoring circle uses a relational mentoring stance (Fletcher & Ragins, 2007) especially exploring issues of power which can affect mentoring relationships. Circle participants seek to establish communication styles and trust which encourages participants to share vulnerabilities with each other (Zachary & Fischler, 2014) while seeking to learn from experiences through discussion and reflection.