This paper focuses on an investigation into the role of information technology in the lives of Lebanese school principles. The objective of this research is to identify Lebanese school principles’ perceptions of the barriers, benefits and negative consequences of information technology usage by listening to their views and experiences. Findings of this research indicate that Lebanese school principles faced challenges including psychological and physical barriers to technology usage. This research can serve as a basis for enabling to make an informed decision about designing future information technology training sessions that can accommodate and serve the Lebanese school principles’ specific needs.