Leadership development (LD) is critical in peacebuilding and crises management where leadership decisions have far-reaching consequences. As organisations navigate turbulence, agile leaders who can deal with information extremes, take critical decisions, and deliver change are needed. We find contemporary LD approaches are conceptually not geared to deliver such leaders. From a development perspective, the problem lies in the preponderance of reductionist ideas, an overwhelming focus on managerial skills and competencies, and a short-term outlook on development that diminish the value of leadership courses. This exploratory article emphasises the value of LD and proposes a rethink in how LD is approached at individual and organisational levels. A holistic, flexible, and longitudinal approach—the whole person approach (WPA)—is proposed, which encourages individuals and organisations to work jointly towards LD. WPA is equally relevant for other sectors and organisations where volatility, uncertainty, complexity, and ambiguity affect positive change.