Only a few studies explore the effects of family management (FM) on entrepreneurial orientation (EO) and hold conflicting positions. Thus, we attempt to shed some light on how FM impacts on EO. Past empirical studies tend to overlook the multifaceted nature of the concept of FM. For this reason, we conceive FM not only as the number of generations involved in the management of the firm (NGI) but also as the percentage of managers who are family members (PMFM). We contend that the benefits of NGI, captured in previous literature by the stewardship theory, should be coupled with the costs of involving several generations, introduced by the so-called stagnation perspective. These costs are related to the ownership-management overlap, the possibility of conflicts and the lack of resources that usually characterizes new generations. Moreover, we argue that PMFM induce negative effects similar to the above-mentioned ones, without the benefits that instead NGI brings. Thus, we develop and test a hypothesis on an inverted U-shaped relationship between NGI and EO, and a hypothesis on a negative relationship between PMFM and EO.