Using a naturalistic methodology, this study explored counselors' and administrators' perceptions of the implementation, monitoring, and evaluation of the Middle and High School Supplemental Counseling Program (MHSSCP) at a predominantly Latino high school. Determining how counselors and administrators define their roles in implementing, monitoring, and assessing MHSSCP should affect the program's effectiveness for at-risk students, for whom the program was designed to support. Three major areas of current literature were reviewed for this study: (a) history of public school counseling, (b) Assembly Bill 1802 and MHSSCP, and (c) leadership roles in MHSSCP. Based on participant interviews, five major themes emerged: (a) counselors and administrators implement the MHSSCP to support the district Initiative to increase student achievement for all students; (b) counselors and administrators evaluate the effectiveness of MHSSCP on three measurable student outcomes; (c) counselors and administrators identify inconsistent use of professional standards in current practice; (d) counselors and administrators exercise teamwork and leadership to create an integrated and directive grade-level service model; and (e) counselors and administrators identify the need to encourage involvement of parents of first-generation students. These themes are presented with supporting evidence from the focus group and individual interviews and are verified through artifacts, descriptive statistics, and field notes. The emergent themes suggest that, as counselors and administrators prepare students for college, they are faced with the challenge of changing a culture that is unfamiliar with how best to support college-bound students. Additionally, with greater emphasis placed on preparing students for college comes the challenge of continuing support for non-college-bound students, which can be addressed by offering courses in career and technical education. Finally, the effort to align counseling programs to state and national standards continues to be slow. The study provides an understanding of how counselors and administrators are caught between meeting established practices and embracing new roles and expectations. [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.]