This qualitative method with a multiple case study research design probed the factors and concerns of three individual business leaders, the internal documents, charts, and graphs supplied, and the external information about each respective organization when they considered the implementation of their respective telework program. Thus this research concerned itself with the business leadership issues involved with the decisions to implement a telework program such as the retention of employees, cost savings, security of data transmissions, cultural issues resulting from a virtual work environment, and the use of technology in support of a telework environment. Considerable research had been conducted about teleworkers, their home environments, conflicts resulting from telework, and family relationships of teleworkers. This research study focuses on leadership issues faced by the decision makers within the three participating organizations. The findings of this research study suggests that leaders who effectively plan and organize a telework environment do so to improve employee quality of life, increase productivity, decrease employee turnover rates, reduce automobile traffic thus reducing the carbon footprint of the organization’s workforce, and reduce the costs associated with the operation at each organization’s central work location.