There is no shortage of scholars that believe that traditional, top-down leadership is antithetical to facilitating the improvements that must be made to the American educational system if all children are to achieve academically. These scholars call for distributive, facilitative, and/or collaborative leadership, yet little is known about how school district leaders can facilitate organization-wide shifts in decision-making practices. Additionally, the study of district leaders is usually limited only to school superintendents. There is a lack of research into the role and influence of the top central office administrators that superintendents directly supervise. These top central office administrators assist superintendents in a number of important tasks, including managing the day-to-day work of the district, evaluating school-site leaders, strategic planning, generating administrative procedures, and recommending policies to the school board. This action research project followed the efforts of one superintendent and his top district administrators as they began efforts to transform the culture of their district to one that encouraged collaborative decision-making. The project utilized qualitative data obtained through individual interviews with the superintendent, all the members of the district's executive leadership team, and half of the district's 25 school principals. These interviews were conducted approximately seven months into a Facilitative Leadership training initiative that included all administrators. The study found a high degree of support amongst all administrators for making more district decisions in a collaborative manner. However, success in increasing the prevalence of collaborative decision-making was limited by the superintendent and district office administrators sending mixed signals to the principals, the challenges of administrators finding time to meet together, and administrators continuing to view their roles in hierarchal ways. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]