This paper draws from phenomenological research exploring the nature of relationships in education, collaborative research exploring alternative pedagogies in educational leadership programmes and postgraduate students’ experiences of leadership. These inquiries have been brought together with the aim of outlining two pedagogical approaches which evoke an appreciation of, and contemplative stance towards, the relational sensibilities within the lived experiences of practising, emergent and aspiring educational leaders. Relational sensitivity and sensibilities are essential to how leaders show what matters in their immediate context. Relational sensibilities appear to have an enduring and ontological presence within experiences of leadership. Examples include a leader’s attunement, nous, tact and improvisation. In addition, sensibilities include how leaders remain resolute having made a moral judgement. Two pedagogical approaches that deepen leader’s relational sensibilities are outlined. One includes the interpretive and hermeneutic use of experiential stories in inquiries of leadership as a phenomenon. A second pedagogical approach, an appreciative appraisal, involves the application of Appreciative Inquiry to the life-centric nature of an individual’s professional practice. It is critically important that leadership courses engage leaders in pedagogical approaches that engender a deepening appreciation of relational sensibilities in their everyday lives. This concern underpins the need for those in leadership to revisit their everyday humanity as this leads to action sensitive praxis.