Digitalization is the most recent and still ongoing industrial revolution, which challenges the traditional leadership theories while also organizational storytelling needs to be revised. This article summarizes the focal phases of leadership theory development while the focus is particularly on organizational storytelling. The purpose is to reflect leadership (theory and practice) in terms of digitalization by discussing such questions as how digitalization has been taken into cognizance this far and how digitalization will transform organizational storytelling and leadership in the future? Three illustrative empirical cases have been applied with a view to reveal insights on the nature and development of organizational storytelling during the last three decades. Also, the use of technology in storytelling is discussed as well as the participative nature of storytelling as a leadership approach. As a result of the theoretical and empirical considerations, the article proposes even Utopian insights to the future by combining prior research, media discussions and movie fiction with a view to stimulate and provoke further discussions.