Contemporary society poses unprecedented challenges to education. We live in a global and varied environment, where not only access to knowledge is essential, but also the development of cognitive and interpersonal skills in students. Educational institutions must adapt to this context, which requires far-sighted leaders to transform the vision of learning. Current reforms, focused on performance and short-term goals, can hinder collaborative and democratic leadership. This qualitative study describes the results of the first phase of implementation of a deep learning facilitation program in educational institutions in Chile, focusing on understanding the resignification of the vision of learning, learning and challenges for school leaders in the period studied. From interviews, surveys and evaluations, it is reported that most understand deep learning, but with variations in its implementation. It also identifies the learnings and challenges of leadership teams, key aspects at the organizational level. The study reveals the challenges and achievements of leadership teams and the critical points at the organizational level, which leads to reflect on current educational practices and the structure of educational systems.