The NYC Leadership Academy has been coaching school leaders for over a decade. The Academy is regarded as a national leader in the field of coaching and the organization continues to expand, learn, and refine its coaching work. Over the years their coaching practice has evolved as they learned more about the practice of supporting effective school leaders. This capstone describes my efforts to help the organization improve on this strength, leading a small group of coaches within the Academy in articulating what leadership coaches need to know and be able to do to facilitate strong leadership development. I discuss the challenge of surfacing what NYC Leadership Academy coaches have learned about effective coaching over the years while also creating space for new thinking and learning about coaching practice. I argue that leadership coaching needs to advance equity in schools and have a balanced focus on both instructional leadership and broader leadership skills like communication and building trust. Helping an organization improve in an area of strength is much like the practice of coaching -- it requires building trust, leveraging relationships, asking the right questions and facilitating reflection, and capitalizing on the interests of the coachee (or organization). This capstone offers important lessons for practitioners interested in leadership development; for NYC Leadership Academy in its effort to expand and refine its coaching practice; and for myself as a coach and education leader. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]