Well-reasoned leadership theories are described in many academic books, yet they may not apply specifically to practices in higher education. In higher education, the absence of tailored leadership theories is compounded by the lack of technical skills or leadership ethics, resulting in leadership issues that impact the organization. To illustrate the effect of the true gaps between leadership theories and practice in higher education, the authors provide a scenario. The intention of this article is to demonstrate that applying theory to practice will assist leaders in guiding followers in the right direction, for the benefit of these specific stakeholders, as well as for the academe at large. The conceptual framework encapsulates: (a) the interaction of one's teaching philosophies and teaching theories; (b) the interaction of one's teaching philosophies and leadership theories; and (c) considerations regarding learning organizations and their success using a flat organizational model.