The purpose of this study was to examine how school counselors', and principals' primary counseling goals and expectations impact postsecondary enrollment in order to learn what best helps students achieve their postsecondary goals. It was found that school counselors' expectations of students were positively related to students' postsecondary education decisions. Further, it was found that principals' primary school counseling goals; regarding preparing students for postsecondary education, was significantly related to an increase in students' decisions to enroll in postsecondary education. These findings support existing evidence that school counselors' high expectations and principals' primary goals are crucial in promoting college-going culture, which may ultimately pave the way for students to attain their goals of earning a college degree.