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This study highlights activities used to create a trustworthy and confidential co-mentoring circle among K-12 educational leaders. The participants were graduate students in an educational leadership program, including principal/program administrator certification candidates. Co-mentoring circles have been developed, refined, and evaluated by Author-A over the past 10 years as safe, learning-filled spaces for aspiring educational leaders to discuss their work as K-12 educators and as principal/program administrator certification interns. 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 co-mentoring circle discussions helped them process the challenges of their work in K-12 schools.