Formation of collaborative settings (virtual organizations, collaborative network organizations, etcetera) is hindered by the lack of trust between unfamiliar but potential partners. Gamification is the application of game design principles to non- game environments. We claim that incorporating the concepts of gamification into Virtual Organisation Breeding Environments (VBEs) leads to building trust between VBE members, as well as motivating them to be proactive members of the VBEs that contribute towards the flourishing of VBEs. This paper explores a novel gamified approach, supported by a suitable methodology, to address the relatively neglected concept of ‘preparedness’ of VBEs.