The role of school superintendent has become increasingly complex. As school district leaders deal with new curriculum standards, increased accountability, and limited financial resources, they are in need of quality professional development tailored to their needs. This qualitative study explores personal, cultural, and structural factors that impact executive coaching for school superintendents. Executive coaching, a widely accepted practice for supporting CEO's in the business world, offers unbiased feedback and help developing solutions to complex issues. Existing research establishes the appropriateness of executive coaching for school superintendents, but does not address how to make it more widely available. This study compares the experiences of superintendents who have been coached with those who have not. Through interviews of coach/superintendent pairs, coaching program leaders, and non-coached superintendents, four coaching models were examined. It considers the various uses of superintendent coaching, and identifies factors that impact its implementation. The findings extend much of the business research into the school setting. Results suggest that coaching positively impacts superintendents and their districts, offering more benefit than other models of professional development. Cultural factors, including the influence of boards of education and superintendent colleagues, have a strong impact on coaching success, as does a lack of clear coaching vocabulary. Personal factors--coach and superintendent attributes, and coach/superintendent relationship also were important. This study may benefit superintendents who desire meaningful professional development. It also benefits those who coach superintendents. Organizations that serve superintendents and school boards may also benefit. [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.]