With the increasingly global nature of our economy, heightened complexity of jobs, emphasis on enterprise agility, and an increase of American telecommuters (approximately 17.2 million in 2008 compared to 12.4 million in 2006* (“Telework Trendlines,” 2009), many companies have adopted distributed, or “virtual”, teams into their organizational structures to successfully operate in changing business conditions. Research suggests that the implementation of virtual teams can provide organizations with many potential benefits—remote working options to greater attract and retain employees (Cascio, 2000), enhanced project decision quality stemming from the firm’s ability to place the best individuals together on a team regardless of geographical location (Lipnack & Stamps, 1999), closer contact to customers worldwide (Solomon, 2001), along with a host of others. However, the benefits afforded by virtual teams are also coupled with many challenges—such as effectively monitoring and evaluating virtual team performance. This paper aims to provide insight into what current research has identified as the major roadblocks in monitoring and evaluating virtual team performance, along with research-derived recommendations regarding how to improve upon these challenges.