From a behavioural perspective data-driven decision making enabled through tracking of online behaviour and communication may afford school organizations the ability to gain insight into behavioural intention. Traits common with Machiavellianism in online behaviour on social media websites lends itself to spying to increase the users repertoire of “advantageous” information to use. This study considers the potential student benefits attributed to tracking online behaviour and collection of “advantageous” information found online in schools including the development of leadership, citizenship and critical thinking, as well as enabling data-driven decision making and evidence-based psychology. Data and results from a two-year qualitative study provides insight into school administration and information technology staff experience with technology policies and the collection of student data.