In this paper, we report on the design and implementation of a state of the art Student Information System (SIS) being developed in a moderate size Alberta, Canada school jurisdiction. The SIS design is premised upon transparency, balanced, comprehensive, and multi-method assessments that links qualitative and quantitative data in support of enhanced, evidence-based instructional leadership. Practical examples of data analytic strategies are discussed in relationship to educational leadership enhancement. The article concludes that as SIS design evolves more optimal, data informed supports for student learning will be realized.