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Focusing on mentoring practices of future educational leaders by their university-based mentor, this paper reports the findings from using an auto-ethnographic approach, developed by the author, based on portraiture (Lawrence-Lightfoot & Davis, 1997) to mentor future educational leaders. The self-portraits were written in a graduate course that focuses on leadership development and practice related to community engagement and communication. The self-portraits of graduate students in this educational leadership course were coded for themes that could be used as a mentoring tool for mentees’ self-evaluation of their leadership stance regarding community engagement and communication practices. Four overarching themes were found: cultural and familial backgrounds, power and expectations of teachers and parents, students who struggle, and the curriculum and hidden curriculum.