Leadership has been considered as an essential foundation for universities to flourish, more so in the context of emerging higher education systems. Using an exploratory qualitative approach, this paper reviews the challenges and prospects in the development of higher education leaders in selected countries of the Association of Southeast Asian Nations (ASEAN). While variations were reported by the respondents, the challenges were somewhat similar: lack of leadership development policy and training centres, the non-availability and questionable quality of programmes, the irrelevance of western and corporate leadership theories, and the lack of systematic talent management programmes. For the lower income countries' respondents, contextual issues seemed to affect leadership development. Since there seems to be inadequate leadership development systems in most ASEAN countries, we propose a synergistic approach among stakeholders with tracked records in intra- and inter-regional level capacity building to design and monitor programme implementation.