This paper examines how societal cultural values and the economic well-being of a country can predict school leadership and autonomy, two managerial indexes within education measured in the Programme for International Student Assessment (PISA) test. Regression analysis (n = 70 countries) indicated that societal cultural dimensions, as measured by Hofstede's model, have significant predictive power for both indexes. Specifically, study uncovered that the Power Distance and Individualism dimensions have a positive relationship with educational leadership, while Long-term Orientation and Uncertainty Avoidance have a negative relationship. Furthermore, study identified a negative relationship between school autonomy and the Masculinity and Uncertainty Avoidance dimensions. A country's economic well-being, measured by GDP, is identified as a significant factor in educational leadership, with countries with higher a GDP scoring lower in educational leadership, however, GDP was not a predictor of the autonomy index. The study uncovers the under-researched connection between PISA and societal cultural dimensions and highlights the importance of contextualization in terms of societal cultures.