This article explores Jacques Ellul's challenges to Christian educators in a society permeated with technique or technological thinking. Responses to the three challenges Ellul puts forth to believing Christians, and, specifically, to Catholic Christian school educators, integrate a process of contemplative practice. This process integrates Catholic tradition and scriptural-based Gospel values with the practice of school leadership. The process focuses on the mindfulness required of leaders to make daily decisions coherent with a professed faith. Final reflections of the article argue the importance of critique and contemplative practice to prepare future Catholic Christian educational leadership. The article suggests that the responses to Ellul's challenges within Catholic education serve as an example to all faith-based education.