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The disproportionate representation of women in K-12 school leadership positions may be reduced by providing supportive mentoring opportunities. Using survey response from 143 school site administrators in California, this study examines the perceived quality of mentoring experiences, perceived effectiveness as instructional leaders, and their association. Furthermore, differences due to mentor-mentee gender pairings are explored. Evidence was found to suggest that the quality of the mentoring experience is related to instructional leadership effectiveness. Moreover, when the relationships were investigated separately by gender, the association was only found for female participants. Analyses based on gender pairings also revealed gender-specific differences that suggest steps towards reducing sexism among school site leaders may be needed.