As an introduction, a starting point is to identify the stressors within IT employee environments. Research has identified the following factors that negatively affect IT professionals: intensive work demands, complex relationships with others, career concerns, systems maintenance, role ambiguity, tedious administrative tasks as well as fear of obsolescence, team and client interactions, role overload, work culture issues, technical constraints, and competing work and family demands (Lim & Teo 1999; Rajeswari and Anantharaman 2003). Given these factors, there is growing amount of research on the supervisory environments of IT professionals that can affect positively or negatively affect employee engagement along these dimensions. Major et al. (2007) find that IT employees respond best to supervisory practices as identified by classic leadership theory: task-focused (boundary spanning, performance management, employee involvement, training and development) and person-focused (relationship building, mentoring, stress management, work-family balance). This research aims to explore the relationship between Romanian IT professionals and two types of stress: job stress and work (or organizational) stress. A survey was conducted with over 1500 Romanian IT professionals and data analyzed in order to begin to explore these important relationships. Preliminary findings show that middle management experience the highest stress values as compared to upper management, first-level management and non-management staff. Utilizing correlation and linear regression methods, results indicate that stress values are most influenced by negative attitudes toward work/life balance satisfaction within the IT organization. Job stress is most negatively affected by full-time status and increasing tenure. As for organizational stress, increasing age and previous employment outside of IT (or first employed position) lead to increased scores. Our paper concludes with some preliminary recommendations for reducing stress in the workplace while also looking at benefits packages for any possible ways to reduce stress in this area of human resources.