The South African educational system is in a crisis. This situation places huge demands on school principals and school management teams, and raises many theoretical and empirical questions. Transformational leadership is needed to deal with these challenges and complexities. Not all school leaders show the same level of transformational leadership. Some leaders conform more to other leadership styles. The aim of this article is to explore the relation between spiritual character traits and leadership styles from a theoretical and empirical perspective. The theoretical part focuses on the conceptualisation of leadership (styles) and spirituality. The empirical research consists of a web-based survey conducted in some private and religiously affiliated schools in South Africa in 2011–2012. The Multifactor Leadership Questionnaire (MLQ) and Cloninger’s shortened Temperament and Character Inventory (TCI-140) were used to measure leadership styles and spiritual traits respectively. Statistical procedures included confirmatory factor analysis, correlation (Pearson rho) and regression analysis. Key findings are that leaders of private schools in South Africa mostly conform to a transformative leadership style, disagree with corrective leadership and strongly disagree with passive-avoidant leadership. Regarding the spiritual character traits they agree with self-transcendence and strongly agree with self-directedness. Spiritual character traits are strong predictors for transformational and passive-avoidant leadership. Higher levels of self-transcendence and self-directedness are strong predictors for transformational leadership. Our research suggests that traditional religious variables are less important as predictors of leadership style than spiritual character traits.