School leaders are regularly required to make decisions concerning the effective integration of ICT into their schools’ teaching and learning programs. School leaders however, face challenges about the processes to use to inform their decision-making. These challenges include knowing which data to draw upon; how to collect the data and how to analyze it so that meaningful decisions can emerge. As such, this chapter examines some recent activities aimed at using data to inform leadership and management strategies in schools as they pertain to teaching and learning with educational technologies, and focuses in particular on total cost of ownership and total value of ownership models for assisting school leaders to make judgements about teaching and learning with technologies. This chapter brings together for investigation the relationships between pedagogy, IT infrastructure, organizational development, asset management, and school financial models to explore approaches to data-driven decision-making in relation to technologies in schools.