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This chapter explores the development of middle leaders in the specific context of Catholic schools. It considers the interplay between contemporary thinking on educational leadership and the insights of Catholic theology and ministry. Two key themes foundational to this interplay are examined: the connection between leading and following, and the central importance of relationships for leadership. For each of these themes, the reader is provided with related questions for middle leaders in a Catholic school context, an activity for engaging with leaders, and an exercise inviting middle school leaders to reflect on their own experience and the context within which they lead.