The development of complex organisational ecosystems that reflect complex adaptive systems (CASs) calls for radically different strategic approaches with respect to the case of classical, stable hierarchical systems. A need for such strategic approaches especially increases in the contexts that lack cooperation traditions and trust and often require an explicit or implicit leadership in order to encourage and maintain development. However, the scientific literature still gives limited attention to strategic approaches to development by emphasising the latter’s dynamism. In order to contribute to filling this research gap, a qualitative, multiple case study of nine Lithuanian clusters representing a variety of industrial settings was conducted to reveal the enablement of the development of complex organisational ecosystems. The performed research enabled to reveal different strategic approaches in two different stages of the development of complex organisational ecosystems. In the initial stage, the experimentation strategic approach, the external agent strategic approach and the strategic approach of the ad hoc clustering of fellow professionals can be distinguished. In later stages, strategies that vary by the degree of involvement of the ecosystem members, such as the strategic approach of self-organisation, the strategic approach of coordinated self-organisation and the strategic approach of active coordination, are more explicit.