This qualitative phenomenological research study focused on eight deans of students at the high school level and three administrators who were instrumental in creating or reestablishing and supervising the position of dean of students within their high schools. The purpose of the study was to define the roles and responsibilities of the high school dean of students as well as determine if this position would be considered critical within secondary education. Upon identifying distinctive characteristics among these high school deans of students, the researcher developed a proactive professional development training model of the high school dean of students' position that could be used by secondary administrators interested in establishing or re-establishing this position within their high schools. This model can serve as a component of a professional development training program to prepare and enhance the skills of individuals interested in becoming a dean of students. In addition, this model could potentially have a universal value to all secondary school districts utilizing the title dean of students. Data were collected from surveys and personal interviews with each participant. The interview protocol and survey were reviewed and validated by a team of professionals from Robert Morris University. Also, job descriptions from six high schools were obtained and used as additional resources as the researcher coded for themes. Data were analyzed and coded by hand after combining Marshall and Rossman's (1999) analytical phases with Lichtman's (2010) six step procedure to arrive at five themes that assisted in defining the role of the high school dean of students. As a result of the findings, the role and responsibilities of the high school dean of students mostly emulated the position of the high school assistant principal with some characteristics similar to the dean of student affairs within a university. The underlying reason for establishing the high school dean of students' position was to handle disciplinary issues. However, it was found that the role of dean of students was responsible for a variety of tasks per request of the high school principal and administrators. Essentially, the high school dean of students became an umbrella position that utilizes a variety of roles and is defined in accord to the needs of that particular high school at that time. [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.]