This case study examines the National College Advising Corps advisers’ perceptions of their preparedness to assist and encourage underrepresented and low-income students to matriculate to a postsecondary education. The methods utilized in this study were qualitative in nature. Four semistructured questions were asked of the 10 participants who were members of the National College Advising Corps (NCAC). Purposive sampling was utilized based on gender, ethnicity, and first-generation status and was reflective of the NCAC chapter’s demographics. The interviews were transcribed with codes and themes assigned to the participants’ responses. Peer debriefing was utilized in validating the participants’ responses, which provided insight on what preparation was effective and insight on ways to improve the preparation of advisers. The participants were actively involved in coaching and mentoring students. They spent the majority of their time assisting students in the functional tasks of completing admissions, financial aid, and scholarships applications. The preparation that they received prior to assisting students in their respective high schools was sufficient for the participants to accomplish their assigned duties. Learning while performing the functions of the adviser position was critical because the initial preparation could not cover all situations that the participants could encounter. Preparation for tasks outside the functional area was noted as being deficient at varying degrees. Once advisers started working in their assigned schools, they generally had issues with managing their time in light of the numerous tasks to be completed each day, asking other school staff members for assistance in preparing students for college, ensuring that they maintained a balance between work life and personal life, and navigating the relationships between the advisor and school staff. Knowing how to handle these issues was classified into the theme of professional development and was critical to the advisers’ success. Having the right balance of functional preparation versus professional preparation can improve the participants’ success in assisting and encouraging underrepresented and low-income students to matriculate to a postsecondary education.