In the hyper-connected society, the profound and incessant technological transformation, augmented by the pandemic, inevitably reverberates in school contexts, reinforcing the innovative use of digital technology by competent teachers and school managers who are aware of the new forms of learning-teaching, in an inclusive perspective. The role of the school headmaster, as an educational leader, intentionally intent on training and professionally stimulating his teachers, represents a performing figure capable of defining educational guidelines and with them the design of accessible, sustainable, collaborative and inclusive learning environments. The contribution presents data on the exploratory survey that saw the headmistress of a comprehensive school in the Marche region offer evidence of the valorisation of the managerial role in orienting, guiding and providing teachers with ad hoc training tools. This perspective tends to foster the objective of promoting good inclusive digital practices, the result of a plural and democratic didactics aimed at meeting the complexity of needs, special and not, of all students.