Although there have always been differences in how generations navigate decision-making in higher education, highly involved parents have led to conflicting inter-generational educational expectations. This research study investigated the phenomenon of parental involvement and how meanings on educational expectations vary depending on generation. The researcher used generational theory as the theoretical framework and employed Interpretive Phenomenological Analysis. Two faculty, two staff, two students and two sets of parents from Appalachian State University participated in this study. An increased level and depth of parent involvement as compared to in the past emerged as a primary theme. Differing expectations of customer service and the purpose of higher education also emerged as themes. Throughout this study, there is a disconnect between the views of faculty, staff, parents, and students of different generations about what is in the best interest of the student. Understanding these differences and their impact on the perceptions of customer service may be useful for administrators as they provide services to students and their families in higher education. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]