The rethinking of leadership at all levels is required to reach the goals of learning and education in 2030 when learners will take the lead in orchestrating the process and manner of their own learning and in choosing their personal learning journeys. The style and focus of leadership must change in order to prepare learners for a dynamic world that is socially connected by digital technology. To prepare for this change, leaders at all levels can foster sustainable open education activities and initiatives through both top-down and bottom-up transparent approaches. They can pave the way for creating openness by inspiring and empowering people to be lifelong learners. Leaders and managers can enable the cultural change brought by digital transformation within their organizations. The cultivation of the culture of quality is critical, and it must be in everyone's interest; however, it must be empowered and encouraged by leaders. Hence, there is a need for people who have the knowledge, abilities, competences, and attitudes to lead this process and to analyze and evaluate digital work environments.