Purpose Business leaders are facing a change of role as digitalization continues to intensify in organizations. As technological change is bringing back supposedly old virtues of leadership, this study aims to explain the impact digital transformation has on leadership due to organizational size. Design/methodology/approach Cross-border study with experts from multinational enterprises (MNEs) in Austria and small and medium companies (SMEs) in Italy. Findings With increasing digitalization, leadership is becoming more important. In times of social distance, it is essential that leaders actively foster the management of relationships with their employees, manage social processes in their teams and shape change processes. This requires a bundle of skills consisting of effective leadership skills, strong change management skills and conceptual digitization skills. Practical implications Digital transformation is not mainly about implementing new technologies; it is about developing an appropriate strategy in which people are key. Organizations regardless of size need to recognize that digital transformation requires not less, but even more active shaping of the relationships between leaders and their team members. Consequently, they need active leaders who drive, communicate and implement technological change. As leadership and change require time, resources and, above all, attention, executive selection and qualification are critical for the broad integration of digitalization ideas into an organization. Originality/value People, not technology, drive digital transformation, and organizations require leaders, not necessarily technological specialists, to manage the complex changes that comprise an organization’s digital transformation. Technical and methodological skills can be substituted with the use of new technologies, but leaders’ interactional, social, strategic and conceptual skills are gaining in importance.