Technological transformation should lead to enhance people’s potential and the development of their cognitive and social competences, especially those connected with effective communication on different levels. The COVID-19 pandemic has intensified all these processes and, for better resilience and effectiveness at work, it requires now different sets of competences. This book gives direct insight into changes that take place in education in the context of an unprecedented and rapid technological advancement, which requires the reorientation of goals and functions based on innovative, adaptive and flexible solutions – in most cases driven by individual leadership. It describes the way to reach this reorientation and shows through thorough research how educational leaders position themselves on this way in this fast-changing ecosystem. Exploring how educational leaders manage the challenges of digital transformation, using European collaborative projects, this research volume discusses how this process impacts the effectiveness and sustainability of organizational activities. Establishing a model for assessing digital transformation in educational organizations and evaluating the effectiveness of their leaders, it will be of value to researchers, academics, practitioners, and advanced students in the fields of leadership, organizational change, management of technology and innovation, and those interested in the development of education and the utilization of digitalization.