The role of Small and Medium Enterprises (SME) has been intensely studied in the management arena. Further, the goal of this study understands how a SME's context affects entrepreneurial behaviors in both men and women. In particular, women in managerial organizations suffer from a silent form of discrimination “glass ceiling”, and they can break it to balance themselves in a “glass cliff”. To break the “glass ceiling”, women show technical or leadership skills. Authors suggest that the environment can explain the managerial behavior, SMEs versus public institutions. Furthermore, the role of leadership and biological gender play a crucial point to explain how managers behave face to a social dilemma. In this study, we propose an experimental analysis to measure the collective behavior in a specific social dilemma among two different samples, SME owners and management directors from the university. This small characterization confirms different behavioral patterns across the two different groups, in particular the found that the environment (SME vs public institutions) explain the differences in collaborative behavior. Further, the interactive effect between authentic leadership and entrepreneurship status on an individual's contribution to a public good will also vary according to the individual's biological gender.