"At-risk" students have been identified to be the main population affected by the "achievement gap," which refers to the disparity observed when certain groups of students have a high probability of not graduating high school, not pursuing a higher education, or not completing a degree at a university level. This thesis explores how constructing the notion of "at-risk' is a communication process that influences decisions on how to close the "achievement gap." It has caused the establishment of several distinct school reforms and programs like San Diego State Universities' Compact for Success which provides advisors to educate and support students about options for higher education. Using an ethnographic approach, I have examined how advisors construct "at-risk" and student "success" to high and middle school students participating in the guaranteed admissions program. The findings reveal that the notion of "at-risk" is defined by five educational benchmarks, while "success" is an undefined term among Compact Advisors. More so, the communication techniques used by Compact Advisors facilitate motivation towards the undefined "success." The findings are beneficial to several disciplines, primarily the communication and education fields, because it promises to shed light on the understudied process of mentoring and college transition programs that guarantee admissions to "at-risk" students.