To anticipate the future needs of principal preparation, it is important to understand past efforts to bridge the preparation and practice gap. Decades ago, both the military and corporate industries discovered that classroom training was not meeting their needs for preparing soldiers and business professionals for real-life challenges. So they shifted training from classrooms to on-the-job training. Further assessments showed that leaving classrooms behind did not solve the problem. So they turned to a combination of classroom instruction and on-the-job training, which entailed a back-and-forth method of learning basics and concepts in class, application of the concepts in real-life situations, and back to the classroom for reflection, assessment, and further learning. This model is still widely used today and offers a viable partnership option for universities and school districts to consider when preparing principals. In this article, the authors discuss the issues surrounding principal preparation and practice divide and suggest that effective principal preparation requires a partnership between school districts and universities. (Contains 3 online resources.)