This case highlights a school principal's leading practice as she worked to transform the social and educational status of students, teachers, and community in a small urban primary school. We employ shadowing, a technique popularized in work-based education and photography, as reflective and research tools. Teaching notes provide insight into the implications of shadowing for leadership development and leading learning particularly in the absence of systematic and strategic professional learning for school leaders in Trinidad and Tobago. The literature used here considers understandings of the relationship between the practice architectures of school leading, the reflective practitioner, and school transformation.