Digitalization requires organizations to quickly adapt to technological trends for sustaining and improving their market position. To ensure they are capable of responding quickly to such trends, organizations implement a new leadership approach, which research and practice refer to as Digital Leadership (DL). The previous literature considers organizations from the information technology (IT) industry as frontrunners in developing DL. While it has focused on the skills of the digital leader and defining DL, our study addresses the so far unexplored development of DL at routine level. We conducted 24 interviews with followers and leaders in the IT industry. Analyzing the transcripts of those interviews with the theoretical lens of organizational routines, we contribute to DL research. We shift the narrative in this field from defining what DL is to understanding how DL is developed by the actions of leaders and followers through artifact-based transformation of DL routines. We identify artifacts in six roles that stabilize or flexibilize performance of DL routines. We uncover that DL is not static but dynamic as flexibilizing artifacts promote adjustment in routine performance based on situational context. Leaders and followers can impede DL development by deciding to situationally deviate from the intended role of artifacts due to tensions between artifacts and past experiences. These findings advance DL theory by uncovering the importance of followers in DL and leadership theory by adding the lens of routines to leadership development. They help practitioners to understand the complexity of DL development and how the IT industry realizes DL.