Future of Work and Digital Management Journal 1 Serial Number 2 2023 10 01 Exploring Leadership Strategies to Foster a Culture of Digital Experimentation Exploring Leadership Strategies to Foster a Culture of Digital Experimentation 57 67 EN Journal Article 2023 08 19 <table> <tbody> <tr> <td> <p>This study aimed to explore the leadership strategies that effectively foster a culture of digital experimentation within organizations undergoing digital transformation. This qualitative research employed a phenomenological design to investigate the lived experiences of organizational leaders. Data were collected through semi-structured interviews with 22 participants from public and private organizations in Tehran, selected via purposive sampling. Interviews were conducted until theoretical saturation was reached. The transcripts were analyzed using thematic analysis with NVivo software, following open and axial coding procedures to identify key themes and subthemes related to leadership behavior, organizational culture, and structural support mechanisms. Three major themes emerged from the data: Visionary and Supportive Leadership, Organizational Culture Enablers, and Resource and Structural Support. Participants emphasized the importance of articulating a shared digital vision, promoting psychological safety, empowering teams, and modeling experimental behavior. Culturally enabling practices such as celebrating small wins, fostering cross-functional collaboration, and encouraging open communication were also identified. Infrastructural supports—including access to prototyping tools, dedicated innovation time, and alignment of performance metrics with learning outcomes—were reported as essential. The findings suggest that leadership for digital experimentation is most effective when symbolic, cultural, and structural strategies are holistically integrated and contextually adapted to the organizational environment. The results highlight that effective leadership for digital experimentation requires a multidimensional approach involving psychological, cultural, and material interventions. Leaders must not only articulate visionary goals but also create inclusive, risk-tolerant environments supported by tangible resources. These strategies collectively contribute to organizational agility and innovation capacity in digitally dynamic environments.</p> </td> </tr> </tbody> </table> https://www.journalfwdmj.com/index.php/fwdmj/article/download/18/19