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Our Educational Leadership (EDL) program collaborated with a large urban district to provide coaching support for 27 administrators. Administrators were identified through the recommendation of their supervisor and university faculty with the goal of increasing and retaining the number of Black male and Latinx principals in the district. Utilization-focused program evaluation (Patton, 2008) was used to examine coaching practices that acknowledged the context and equity issues in the district. Results revealed the need for addressing career mapping, instructional leadership, mentorship and coaching from Black male and Latinx mentors/coaches. A cycle of inquiry allowed for a consultee-centered approach designed to help principals navigate the experiences needed to progress toward the principalship and successfully thrive in current and future leadership roles.