Information technologies in today’s world function as support net for sharing knowledge and information coming more important as well as promoter of mutual cooperation when it comes to development of further education of adults. Because of a passive cooperation between educational institutions and enterprises, society is still in search of approaches and methods, new information systems and technology to improve service of knowledge, skills, abilities and attitudes. The research aims to justify and develop the knowledge sharing imitation model and prototype for trilateral cooperation. The goal involves innovative methods and web-based automated cooperation system. The main study question is what kind of modelling tools and technological solutions can be applied to improve and automate knowledge sharing efficiency and cooperation indicators? The results of this research are intended to be used in practice as promotional technology of cooperation development between potential interns/working individuals, adult educational institutions and enterprises.