The purpose of this qualitative study was to investigate how students at Henry Lord Middle School in Fall River take into consideration their initial college and career aspirations when making their decision for high school. Self-efficacy theory, critical theory, and a literature review related to high school decision-making inform the analysis of data regarding the three research questions framing this study: (1) What influenced Henry Lord Middle School eighth grade students' decisions when selecting a high school of attendance?; (2) How are parents or guardians of 8th graders at Henry Lord Middle School informed of the high school options and influence their children's high school decision-making process?; (3) How did guidance counselors influence the high school decision-making process for transitioning eighth graders from the Henry Lord Middle School? To answer these questions, a case study approach was used to assess students' perceptions of how they reached their decision for high school, to assess the influence of family members on that decision, and to identify the information used by parents in support of that decision at Henry Lord Middle School. One hundred and sixteen middle school students participated in focus groups along with seven family members and a guidance counselor for the school to determine student, family, and guidance counselor perspectives on Henry Lord Middle School students' decision-making for high school. Themes identified through an analysis of focus group results were then used to identify cross-stakeholder perspectives. These perspectives ground recommendations for improving the middle school guidance program and the transitional services at Henry Lord Middle School. [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.]