The process through which most aspiring superintendents are prepared for their craft, university-based superintendent preparation programs, have for some time been assailed by an array of nationally respected critics and organizations. The basis of their disparagement is grounded in the wide-ranging conclusion that these programs are out of kilter with the present day specialized needs of would-be school executives. The critics draw support for their perspective by accentuating the observation that the contemporary university-based superintendent preparation process has stagnated while transformation in the work of superintendents has evolved noticeably, especially within the last twenty-five years. This study develops a framework for intensive assessment of attributes and components of current university-based superintendent preparation programs as the beginning point of a larger discussion that reconsiders their efficacy and effectiveness. Secondly, the study amasses broad insight from the current literature and from experts in the field regarding how the effort to recreate these programs must be approached as well as who should be at the table for these negotiations to engender productive outcomes. The data that spring from this study should be rich with fresh insight and, as such, should be given ample consideration as professional associations continue to push forward in the struggle for answers to how these programs might be redesigned. At the very least, it will provide several significant clues for future action and should result in a more thoughtful discussion around this issue. In-depth interviews with veteran practicing superintendents as well as nationally prominent scholars add significant value and merit to the study and suggest that its findings and conclusions are deserving of consideration by educators, policymakers, and scholars alike.