This chapter is a brief snapshot on the evolving stages of the principalship of the Kingdom of Saudi Arabia. In the era of economic globalization, new alignment of nations and its politics, and the rise of religious fundamentalism in and around their nation, the principalship in the Kingdom has evolved since the country’s inception in 1932 and been challenged as the country’s social institutions experience fundamental change. This chapter analyzes school leadership literature from past and current studies conducted primarily by Saudis in higher education institutions in English-speaking countries such the United States, Canada, Australia, and the United Kingdom. Due to the scarcity of relevant literature, a few additional studies written in Arabic and conducted in Saudi Arabian universities were appraised. The literature review in this chapter seeks to disseminate the role of a principal across three domains: as an instructional leader, an operational leader, and a community leader. The chapter ends with a summary of current reform efforts intended to improve the overall quality of K–12 schooling in the country, with particular emphasis on the additional responsibilities facing school leaders in an effort to raise student achievement and thoroughly prepare future citizens of the Kingdom with a rigorous and comprehensive academic foundation.