This chapter provides an understanding of the imbedding of corporate social responsibility (CSR) within small- to medium-sized enterprises (SMEs), through continual learning achieved by organizational development processes. Through an interpretivist case study, we investigated the collaborative relationships of 10 Australian organizations. Benefits of these relationships are reflected in improved returns, increased efficiencies, and enhanced stakeholder relationships. From these benefits, improved problem solving, change intervention, and implementation were evidenced, and supported a causal relationship between positive collaboration and mutual learning. The metaphor of a tree, the ‘collaborative ecosystem model’ is used to explain these relationships and the developmental stages explored; from seed to sprouting of the tree is depicted in terms of theory, corresponding action, and behaviours.