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. To address the problem innovative, individual approach-oriented technological solutions are studied and new knowledge sharing models are created to achieve a sustainable trilateral cooperation process. The research aims to justify and develop the knowledge sharing imitation model and prototype for sustainable cooperation between adult educational institutions and enterprises. The goal involves innovative methods and web-based automated cooperation system. One of the principal objectives is to identify needs and desires of potential trainees/working individuals and representatives of educational institutions and enterprises as well as opinion of experts concerning current situation and possible improvements to promote sustainable cooperation. The results of the thesis show that the applied information technologies play an important role in knowledge sharing and cooperation-promoting activities. Results of thesis provides basis for further inquiries about knowledge sharing, promotion of cooperation and design of support technologies.