Research on school districts has repeatedly found that focusing on student learning and instructional leadership is a key component to effectiveness (Murphy & Hallinger, 1988; Leithwood, 2010; Anderson & Young, 2018). Districts are currently undergoing a redefinition of roles in order to specifically support principals as instructional leaders in their schools. This qualitative case study describes how one district began to develop a system for supporting principals through incorporating leadership coaching. This study shares the perspectives of principal supervisors and other district specialists as they built their own capacities to be effective coaches. The complexity of simultaneously developing skills in both the principal supervisors learning to coach and the principals being coached is contextualized in this study. I find that the self-direction of coaches learning to coach was significant in principal supervisors and district specialists learning to understand the key principles of coaching. As individuals and as a collective of district leaders, it is the element of choice that creates a meaningful beginning to implementing leadership coaching for principals and has set forth a clear vision for the future of supporting principals in their instructional leadership goals.