This chapter establishes the theological, pastoral, and contextual foundations for accompaniment within Catholic school leadership. Drawing on Scripture, particularly the Mamre encounter and its iconographic tradition, accompaniment is presented as a sacred encounter grounded in hospitality, presence, and discernment. The chapter situates accompaniment within contemporary leadership contexts marked by complexity, change, and growing wellbeing pressures, identifying both challenge and opportunity for mission leadership. Informed by interdisciplinary sources including theology, psychology, and neuroscience, accompaniment is articulated as a collegial, non-deficit, and formative practice oriented toward integral human development. The chapter introduces the four interrelated capabilities of Presence, Relationships, Awareness, and Contemplation, outlining their developmental stages and role within a structured conversation process. Together, these foundations frame accompaniment as a practical, faith-informed response supporting wellbeing, reciprocity, and leadership for mission.