This explores a dynamic leadership framework that positions regeneration as both a personal and planetary imperative. Grounded in modern transformational leadership, this chapter emphasizes change that begins within individuals and institutions, cascading into societal and ecological transformation. This inside-out approach reflects core leadership competencies—ethical influence, adaptive capacity, and visionary action—reframed through an ecological lens. Drawing on interdisciplinary models such as Peter Drucker’s leadership arcs, systems thinking, and ethical leadership theory, this chapter highlights the need for leaders to embed sustainability and justice into their practices. Case studies from Unilever, Patagonia, and Salesforce illustrate how transformational leadership fosters innovation, resilience, and inclusive growth. This chapter also examines the role of digital and AI-powered ecosystems in enabling collaborative intelligence and regenerative design. Cross-cultural traditions—Ubuntu, Confucianism, and Indigenous philosophies—enrich the model with relational depth and moral clarity. Systems thinking is treated as a foundational competency for aligning organizational purpose with societal and environmental will. Overall, regenerative leadership is presented as a modern transformational model—one that integrates ethical foresight, cultural fluency, and ecological consciousness to inspire emergent ways of working and sustain long-term value creation in a networked world.