Abstract
Digital transformation (DT) at the micro level implies organizational changes in roles, individual skills, leadership styles, and managerial approaches. Therefore, it is essential to investigate the individual attitudes and behaviors that lead to DT in organizations. Thus, we investigated DT at the micro level to explain the individuals who manage DT. For this, we developed a multiple-case study of 38 Italian firms by analyzing data regarding seven large firms and 31 small and medium-sized enterprises (SMEs) to allow for cross-case analysis. Our findings suggest that approaches differ for managers in SMEs and large firms. In large firms, a “digital transformation conductor” (often called “chief digital officer”) oversees DT processes, whereas in SMEs, there is a “digital transformation peer-tutor” approach to DT. A bottom-up, informal, persuasive, and empathic approach characterizes the peer tutor. However, in large firms, a conductor approach is used to drive the necessary changes.