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Technological advances and the desire for employees to improve work-life balance have contributed to the growth of telework. Finding and retaining effective leadership talent are critical needs of organizations. Recruitment and retention of leadership talent can be supported by access to perquisites such as the ability to telework. Although research on teleworking employees in general, and virtual team leaders, can inform the industry, few leadership models exist that specifically help understand what it takes to be a teleworking leader. The purpose of this phenomenological study of teleworking leaders filled this gap by examining the experiences of 12 teleworking leaders with an average of 21 years of management experience across a broad range of industries. Six themes emerged from the interviews: communication, employee relations, individual leadership experience, employee or work issues, monitoring, and trust. Although many experiences of the teleworking leaders were consistent with existing research on teleworking employees and virtual team leaders, within the 6 themes, other aspects of the experiences within each theme are unique to the teleworking leader such as the development of efficient practices for communicating with employees and the intentional use of remote work for the important leadership activity of strategic thinking. Recommendations for further study include research specifically on teleworking leaders and their best practices that can be adopted by in-office leaders, and research on experiences of employees whose leaders are remote. Implications for positive social change include increased organizational sustainability through improved work-life balance for teleworking leaders and by increasing the strategic leadership capacity of leaders through telework.