This paper contributes to the empirical literature on the relationships between external management in family firms and investments in digital innovations. The analysis is based on a survey carried out by the Italian Chamber of Commerce in early 2018 of 2,342 small and medium manufacturing family firms with at least five employees. We empirically tested the relationship between our variables through ordered probit models and marginal effects. Our results showed that the presence of external managers is positively associated with the probability of investing in Industry 4.0. Disaggregating our sample into two sub-samples, external management was also found to be positively associated with the likelihood of investing in Industry 4.0 only for firms without graduates and with comparatively older owners. Finally, our results suggest that the ongoing extensive and structural transformations require skilled managerial leaderships that perceive the need for the more rapid adoption of digital technologies