In almost all societies, schools are seen as an important base for transferring knowledge and values related to how today’s democratic society works and develops from one generation to the next. Going to school is considered an opportunity for the individual student to acquire the knowledge and skills necessary to make individual choices and prepare for a future job or occupation. Besides transferring individual competence and skills, schools play an important role in how the democratic nation-state is understood and valued. New technologies and AI open possibilities that we have not seen before at the same time as we have large societal and environmental challenges. Taken together, national and global events and processes change values, and norms, and the understanding of the concept of democracy, which have a direct impact on schools and the younger generation. Hence, we believe that future schooling needs to focus on sensemaking, values, and ethics to meet upcoming challenges in which the ambition to support and develop democratic citizens is crucial. This chapter is a commentary that explores these issues and educational leadership based on Swedish education policy documents. We argue for an authentic, values-based, communicative leadership for learning and democratic improvement.