Although improving the college and career readiness (CCR) skills of high school students has become a higher priority in recent years, educators must continue to seek better and more effective ways of preparing students for life after high school. Unfortunately, many high school students continue to be inadequately prepared for college or a career and have not obtained necessary life skills upon high school graduation. To address the need for investigating this problem, this study explored the perceptions and experiences of high school social workers, counselors, and administrators regarding CCR skills of high school students. Aspects of CCR were analyzed and discussed from 10 interview participants as well as programs and strategies found to be successful at improving student CCR skills. Findings indicated many CCR skills overlap, and even though the participants had different ways of looking at life skills, all placed a high value on the development of academic skills, life skills, and mental health skills, each being deemed critical for students as they matriculate to college or the workforce. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]