<p>The success of Disability Support Service Organisations (DSSOs) in New Zealand cannot be separated from the effectiveness, skill, and competence of their leaders. This research examined the effectiveness of leadership practices and competencies on the continued growth, development, and sustainability of these DSSOs and what lessons can be learned from the encounters and experiences of their leaders. Four participants from two organisations in New Zealand were interviewed to obtain data on the experiences and encounters of leaders. This was supplemented by the information gathered from documentary sources. The findings reveal how leaders operate and adapt to the conditions and challenges.</p>