As digital workplaces change due to innovative technologies, managers have to deal with novel expectations of leadership. In more concrete terms, employees tend to prefer enabling leadership styles over coercive approaches. At the same time, information systems (IS) for leadership get more powerful and are applied in support of leadership. In this study, we investigate both the challenges that arise for leadership because of the changes in framing conditions and how these challenges can be overcome. We carry out an explorative Delphi study to build on the experience of a carefully selected panel of experts. We also gain important insights by conducting qualitative follow-up interviews with specific experts from the panel. The findings emphasize the increasing role of employee empowerment. Organizational change is essential to overcome the challenges, and leadership-related IS can facilitate this transformation to a certain degree. In sum, this study contributes to research on leadership in the digital age.