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This study describes a mentoring program for first and second-year Catholic school principals in a large urban diocese, and identifies key challenges, impacts and influences on decision-making. Ten school leaders describe their work and provide the lens by which to reflect on their role as faith leaders. The challenges these principals face along with the various roles they play in their day-to-day work as school leaders are discussed. Based on the perceptions and insights of their roles as faith leaders and how that role is situated within other leadership roles, this study seeks to better understand how the faith leadership role and its development impacts decisions in novice Catholic school leaders.