<![CDATA[Leadership within Islamic educational institutions currently stands at a crossroads between preserving tradition and responding to the demands of digitalization. This article aims to analyze leadership dynamics in *pesantren* (Islamic boarding schools) and *madrasah* (Islamic schools) using an analytical-contextual approach. By examining field realities and synthesizing modern leadership theories, the study formulates solutions to the challenges of technology-based management. The findings offer a novel concept—"Transformative-Synergistic Leadership"—which integrates digital proficiency with the noble values of the *pesantren*. In conclusion, institutional success hinges on the leader's ability to adapt to technology without severing spiritual roots. Leadership in *pesantren* and *madrasah* represents a unique entity that integrates traditional religious values with modern management. This study analyzes the leadership practices of *kiai* (Islamic scholars/leaders) in *pesantren* and *madrasah* principals, as well as the context of their adaptation in the digital era. Through a literature review and qualitative analysis, it was found that *pesantren* leadership tends to be based on the *kiai's* charisma (centralized), though it is shifting toward a democratic-transformational style in modern *pesantren*. Meanwhile, *madrasah* leadership is more formal and emphasizes Total Quality Management. The relevance of leadership in both institutions today depends heavily on the ability to adapt to technology, innovate curricula, and uphold the value of exemplary leadership.]]>
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