The present qualitative study examined the views and perspectives of five Executive Directors of Admissions of Midwestern colleges and universities to seek data on high school students' college preparation level based on the quality factors of the high school they attended. Interviews were conducted using multiple open-ended questions on various aspects of high school characteristics that had potential to impact college admissions and college success. Themes emerged that encompassed high school size, high school offerings, and factors of high school attended. All high schools were not viewed as providing neither equal opportunity nor adequate educational opportunities for all students sufficient enough for them to be admitted to a four-year college or university and/or to successfully graduate from college. Emerged themes of significance included larger high schools being more effective than smaller high schools; Advanced Placement courses being more effective than dual-credit classes; and the rigor of high school curriculum being unequal amongst schools. Each of these themes is identified in detail with examples, experiential stories, and views by the participants. School leaders can use this data as a piece in their continual search to further student success in high schools and beyond. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]