This research study investigated the technological perceptions and expectations of community college students, faculty, administrators, and Information Technology (IT) staff. The theoretical framework is based upon two assumptions on the process of technological innovation: it can be explained by diffusion of adoption theory, and by studying the relationship between wholes and parts, or Systems Thinking. The research is conducted against a backdrop of generational theory and how different generations possess varying degrees of readiness toward technology adoption. The following research questions were posed: Question 1: How do the perceptions/expectations and utilization held by faculty, administrators, and information technology staff of a multi-college community college district surrounding technology differ from students? and Question 2: In terms of technology perceptions/expectations and utilization, are there generational differences within and between various community college professionals and students? This quantitative study used survey research methodology to gather and analyze data from 442 students, faculty, administrators, and information technology staff at four community colleges within one district. The "CDW-G 21st Century Campus Assessment Tool" was sent out via an email invitation to gather the perceptions, expectations, and utilization of technology. With a total response rate of 10.60% (4171), the response rates for each group were: students (11.83%, n = 186), faculty (8.34%, n = 199), administrators (24.13%, n= 28), and information technology staff (29.29%, n = 29). Thirty-five percent of the respondents were members of the Baby Boomer generation, 37% were Gen X, and 24% were Millennials. Results from the first research question revealed the perceptions and expectations held by faculty, administrators, and information technology staff regarding campus technology and the importance of technology to learning and student success do differ from those of students. Additionally, the use of technology devices and email also differ between these groups. The conclusions drawn encourage a focus on professional development for Baby Boomers, allowing for the cross-fertilization of input from Millennials and Gen X and consideration of succession planning in terms of how inputs to an organization will change as younger generations take on positions of leadership and engage in strategic planning and decision making. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]