The role of the business partner in 21st century education has come into greater prominence in the public school system, especially at the high school level. Shrinking budgets have prompted high school principals to explore the idea of business partnerships as a way to close the gap in academic achievement and provide direction for high schools struggling to meet the workforce development demands in today’s society. In addition, financial support has provided opportunities for curriculum enhancement, staff development, and student support. However, as more emphasis is placed on the development of school business partnerships, the need to determine how these partnerships function successfully is a necessary part of the process. This book addresses the historical perspective concerning the involvement of the business sector and their relationship with education throughout the twentieth century. In addition, an exploratory study is provided utilizing quantitative and qualitative data. The purpose is to identify the skills and knowledge that high school principals and their business counterparts need to have in order to create an equitable relationship.