The complex, multi-faceted sustainability challenge that society faces calls for a strategic approach to sustainable development. Strategic planning processes towards sustainability in organisations and communities are oftentimes led by a facilitator or facilitative leader. We argue that planning processes of complex and transformational change, call for collaboration among stakeholders and for highly skilled facilitative leaders who are committed to the development of self, others and society. This thesis explores the ‘interior state’ of facilitative leaders as a high leverage point in moving society towards sustainability. We identify nine personal capacities that enable leaders to facilitate collaboration in Strategic Sustainable Development: (1) Being Present, (2) Whole Self-Awareness, (3) Suspension & Letting Go, (4) Compassion, (5) Intention Aligned with Higher Purpose, (6) Whole System Awareness, (7) Personal Power, (8) Sense of Humour, and (9) Holding Dualities and Paradoxes. We identify a range of personal and collective practices that help develop these personal capacities. We propose these capacities are the foundation for a more holistic and authentic facilitation approach applied to strategic sustainable development.