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The purpose of this study was to explore the lived experiences and mindsets of teachers, administrators, and coaches who have utilized instructional coaching for teacher learning and leadership development in an urban, impoverished high school. The literature indicates that instructional coaching as professional development has benefits not only for teachers and administrators, but also for students. In addition, urban school districts in impoverished settings are faced with a unique situation because the need is significant for quality teacher professional development. Very little is known about the experiences of instructional coaches, especially at the high school level. Using case study as an approach to capture teacher, coach, and administrator experiences with instructional coaching, this study utilized Mezirow’s Transformative Learning Theory, which focuses on learning as a process: through dilemma, reflection, and change as a theoretical framework. Overall, the findings suggest that coaching is heavily influenced by the interrelationships and interdependence of learning and leading. Establishing shared mental models about coaching and working to build common frames of reference about the importance of teacher learning and how it relates to student learning are significant themes that emerged in this study. This study has several implications for policy and practice in the realms of instructional coaching, leadership practice, adult learning, urban education, and higher education.