This research work pertains to the challenge in Academia regarding millennial students and the technological gap that exists between this generation and the current university faculty and staff. In many instances, it is the younger generation of hires (faculty and staff members) who are more attuned to the preferences of this group of students. Moreover, decisions pertaining to crucial changes on campus are most of the time not made at this junior level of new hires. In addition, the concept of tenure and the complacency that tenure at times generates becomes an obstacle to bridging the gap in communication and technological expertise between faculty members and younger students. There is less urgency and earnestness for tenured faculty to keep up-to-date with technological changes. Additionally, those who are still untenured faculty members have their own research to focus on so they relegate updating knowledge in use and implementation of newer technology within their discipline to lower tiers of priority. This research study includes compiled data based on published surveys and assessments that gauge how students, faculty and staff perceive the technological level of their faculty and peers, and discusses how university constituents can consider the effects of technology use on higher education. After myriad data analyses, this research study concludes by providing six institutional exploratory questions centering on moving institutions forward, as well as six periodic campus interrelated activities that can help face and mitigate these challenges.