This dissertation investigated the expectations both professional academic advisors and undergraduate students, respectively, possessed of academic advising and of the advisor role. As students come to their postsecondary endeavors with increased needs, expectations, and consumer-mentalities, it is important to understand their expectations -- and meet those expectations -- to improve student satisfaction with advising (Propp & Rhodes, 2006). Given the increased use of professional academic advisors across higher education institutions, the literature does not speak to their expectations of academic advising. It is also difficult to ascertain how to best perform academic advising to meet student expectations in various contexts because there is a lack of standardization within the academic advising profession (Johnson et al., 2019). Although mass standardization is not the goal (Menke, Duslak, & McGill, 2020), academic advising should be purposefully structured based on institutional and student characteristics (Ender, Winston & Miller, 1982), the strengths of different advisor types (Allen & Smith, 2008a; Reinarz, 2000), and student needs (NACADA, 2005) and expectations (Anderson et al., 2014). Therefore, this hermeneutic phenomenological study explored students' and professional academic advisors' expectations of academic advising and of the advisor's role. Through document review, semi-structured interviews, reflective journaling, and member reflections, I analyzed the lived experiences of students and advisors in order to understand how their expectations converge and diverge. Two of the main findings of the study were a.) previous experiences, in various ways, informed both advisor and student expectations, and b.) student and advisor expectations were aligned in terms of important skills for advisors to demonstrate and important outcomes of academic advising. The results of the study have future implications to inform advisor training and development, and the way in which advising is formally structured across and within various institutions to meet students' needs and expectations of academic advising. [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.]