Given the prevalence and continued growth of teleworking, future teleworkers and their managers need to be informed about the challenges that may hinder effective teleworking and potential strategies for overcoming those challenges. Quantitative and qualitative survey data were collected from 86 high performing teleworkers and their respective supervisors. Semantic themes representing categories of challenges and strategies emerged from the qualitative data. Some of the identified strategies included the use of advanced technology, communicating with family, task planning, and striving for extra productivity. The strategies were correlated with turnover intentions, work-to-family facilitation, and family-to-work facilitation. Implications for the management of teleworkers and suggestions for future research are discussed.