The authors have researched, designed, and engaged in leadership coaching for many years, from many angles and across many district contexts. They have been struck by how rare it is to see a leadership coaching model that clearly aligns with and supports district priorities. To help change that pattern, the authors have distilled the lessons they have learned into five key questions that can guide strategic planning for leadership coaching programs. This article shares those questions, with examples of how the authors addressed them in one large-scale school improvement project, LEAD Connecticut, in which they worked with a varied group of stakeholders to articulate a strategy for school turnaround, a corresponding vision for turnaround leadership, and a strategy for developing and supporting a cadre of school leaders equipped to carry out that vision. The five guiding questions are as follows: (1) What is your vision for effective leadership? (2) What aspects of that vision for effective leadership can coaching best support? (3) Given the knowledge and skills your coaches will help develop in school leaders, what should the coaching look like? (4) Now that you have a vision for effective coaching, how will you ensure that coaches have the skills and knowledge to carry it out? and (5) How will you know if this coaching program is working?