Principals in religiously affiliated schools are called to lead their schools in ways that are grounded in a set of core beliefs and values. This study examines the challenges of leading toward a community of faith grounded in the spirit of major constituencies when one is under-prepared for such leadership. A national sample of lay Catholic high-school principals was queried in order to investigate their reflections on preparedness to be faith leaders of their schools. The strategies they reveal are applicable to private-school principals and to the formal educational programs that prepare them to be faith leaders.