Collaborative Business Ecosystems have been benefiting from the technological advancements, allowing better collaboration among organisations to provide more innovative products and services in an increasingly demanding world. This collaboration can be assessed through a set of performance indicators, which also induce a self-adjustment of the organisations’ behaviour, improving their profile and that of the ecosystem as a whole. In fact, their behaviour is expected to evolve (like individuals) according to the way they are evaluated. As such, this study presents a simulation model, which, together with the performance assessment and influence mechanism, is an essential contribution to measuring and influencing collaboration, enabling better management decisions. The model is based on agents and system dynamics, featuring a business ecosystem populated by organisations categorised according to a different profile, and configured and calibrated according to actual collaboration data. The samples were collected from two established companies operating in the same business ecosystem in the information technologies industry. Preliminary results of this approach, based on some simulation scenarios, are presented and discussed.