Educational management has benefited significantly from general systems theory. However, the foundation for educational management, namely the classical management theory, has largely relied on principles put forward more than 70 years ago. Recent societal challenges and diversification of learning environments have highlighted the need for a new learning design theory, which highlight the importance of leadership. This article describes the issues in educational management from the perspective of Metasystems Learning Design Theory. It defines data-driven educational management and provides two hypotheses, namely that educational management is a meta-science and that the educational management theory has been evolving since the first industrial revolution onward to data-driven leadership. These hypotheses tie together concepts from philosophy, pedagogy, psychology, cybernetics, and management to prove the emergence of novel concepts: metadata, metacybernetics, and metapsychology. Conclusions underscore that data-driven leadership allows anticipate and respond to global challenges and green preferences of life-long learners. The implications are that future studies should apply data to inform instructional design of learner-centered systems & environments