While Learning Analytics (LA) have gained momentum in higher education, there are still few examples of application in the school sector. Even fewer cases are reported of systematic, organizational adoption to drive the support of student learning trajectories that includes teachers, pastoral leaders, and academic managers. This paper presents one such case -- at the intersection of praxis, governance, and evaluation -- from a practitioner perspective. The paper describes the added value of data-driven approaches to create a culture of improvement in students and teachers in a comprehensive coeducational independent day school in Sydney. Evaluating the work done over the past five years to develop LA dashboards, the authors reflect on the process, the inspirations coming from theory, and the impact of the dashboards in the secondary school context. The data presented is not experimental in nature but supplies tangible evidence for the systematic evaluation scaffolded using the SHEILA policy framework. The main contribution of the paper is a practical demonstration of how managers in a secondary school drew from existing literature and observed data to 1) reflect on the adoption of LA in schools and 2) connect the dots between theory and practice to support teachers grappling with the trajectories of student learning and development, thus encouraging students to self-regulate their learning.