One of the most significant management challenges in modern companies and organizations is dealing with unavoidable, complex paradoxes. Today’s world is multidimensional, multipolar, and multipurpose, and increasingly, classic management challenges such as leadership vs. management; exploitation vs. exploration, virtual vs. physical presence, economic sustainability vs. environmental sustainability, localization vs. globalization, etc. assume the characteristics of paradoxes rather than problems or dilemmas. Leadership of paradox is not about making a decision once and for all or prioritizing tough trade-offs, but about navigating between opposing considerations. Navigating Leadership Paradox argues that academic knowledge pools can support leaders’ decision-making and sense-making in organizations and navigating paradoxes. The book outlines a practical pathway for management leaders and professionals for steering through paradox using 5 phases, 10 paradoxes, 15 tools, 20 cases, and 25 learning points. It delineates how to identify a paradox by assessing the nature of your challenge and discusses the appropriate courses of action individually as well in collaboration with other stakeholders. It also gives inspiration and advice for professional helpers assisting others in navigating paradox as part of organizational development or other educational purposes. This book will be essential reading for practitioners and academicians in the fields of leadership paradox, complexity management, change management, leadership dilemmas and organizational paradox.