When the covid-19 pandemic started, managers were only able to lead their employees through digital communication. During the subsequent telework a completely new research area, in need of new knowledge, was created. The purpose of this study is to gain an understanding of opportunities and challenges of remote leadership, experienced by managers. This at a time of only digital communication with employees, with no physical meetings or interactions. The study will answer the following two issues, “What factors are important for managers to take into account when applying a leadership style to teleworking employees?” and “Which internal communication functions in the organization have worked better or not according to managers, when remotely managing employees?”. This exploratory study has its theoretical starting point in situational theory, as well as in Richmond, McCroskey and Powell’s six functions in organizational communication. Through semi-structured interviews, empirical data has been collected and then analyzed through coding, thematization and summation. The result of this study indicates that future managers, conducting digital leadership, will need to take each employee's needs and personal situation into account. Managers need to adopt a functioning leadership style, while keeping important factors regarding employees in mind. This in order to successfully lead each teleworking employee through digital communication.