In the last few decades, the Open Source Software (OSS) diffusion has grown remarkably in companies. In this context, the present study has analyzed the factors that incentivize OSS implementations for enterprise purposes, linking two perspectives: (1) managerial and (2) educational. Thus, the Delphi methodology was applied to a panel of experts with two aims: (1) to know managers’ perceptions about organizational users’ motivations toward OSS after receiving OSS training and (2) to develop a forecasting study to examine the OSS diffusion in the medium term in companies and educational centers. In this context, the Self-Determination Theory (SDT) was the theoretical approach through which we identified the motivational factors. Specifically, three SDT motivations were added: (1) autonomy, (2) competence and (3) relatedness. The 104 selected experts were managers from companies with employees who have studied in educational centers where OSS usage is mandatory. The results show that managers perceive that OSS training incentivizes OSS implementations in companies. At the same time, user motivations are considered to be extremely relevant, especially autonomy. In addition, is the results foresee a similar level of OSS implementation in the business and educational fields in the medium term. Finally, conclusions, practical implications and limitations are discussed.