Regional organisations (ROs) are important in that they can enable states in their regions to pros-per and develop for improvement. Interest here lies in the European Union (EU) and the Associa-tion of South East Asian Nations (ASEAN). Their political development involves complex process-es for collective actions involving ingroup member RO states. To explore development, we firstly examine the rise of both the EU and ASEAN. The literature gives some attention to the behaviour-alist political approach to explain developmental differences using social organisation theory, often in terms of the Gemeinschaft-Gesellschaft paradigm of Tönnies. However, here we adopt a social psychology approach that distinguishes between operative structure (which directly determines behaviour), and substructure (housing normative personality deemed to be responsible for behav-ioural imperatives). This enables a relationship to be made between the Tönnies paradigm and the Collectivism-Individualism paradigm of Triandis. The theoretical approach adopted involves a complex adaptive systems model deriving from metacybernetics, and this also delivers Mindset Agency Theory as a qualitative methodology. Consistent with the general view, it is shown that the EU is more or less a coherent rational organisation, while ASEAN is more idealistic delivering pragmatic paradox. In particular, ASEAN is frequently descried as an organisation with contra-dictions, and for this reason its pathologies are explored in some detail