Why do so many IS/IT-related projects fail to deliver the level of tangible and sustainable performance improvements organizations target and expect? Why are the new mindsets and ways of operating enabled by IS/IT innovations so difficult to be integrated and adopted in organizations? Why do factors such as resistance to change, insufficient executive sponsoring, unrealistic expectations, or ineffective leadership still nullify the efforts put into the implementation of conceptually and technically sophisticated information and communication (including enterprise resource planning, supply chain management, collaboration, knowledge management and similar IS/IT-based) systems? These questions, which are relevant to both IS/IT research and practice, are at the core of a simulation-based experience aimed at deepening and extending our understanding of issues related to managing organisational change and transformation in the context of IS/IT implementation projects, providing at the same time a new approach to model, validate and diffuse efficiently (through a gamelike experience) knowledge in this relevant domain.