This research approaches the issues of introducing ICTs (Information and Communication Technologies) into Small and Medium Enterprises, with the aim of finding some conditions that make the organizational context able to manage the change process needed to really get the potential benefits of these technologies. The final objective is to propose a theoretical base for a methodology able to improve analytical and diagnostic capabilities of organizational realities before and during planning and evaluation phases of their Information Technology investments. The study is planned to go through two phases. The first one is aimed to look for reliable indicators to forecast readiness and adequacy of a specific organizational context towards the positive adoption of I.T. systems through a deep analysis of five significant cases. The second phase will test such indicators through questionnaire research on a larger sample of Italian SMEs.