This study was designed to investigate factors that influence the acquisition and development of interpersonal skills among high school principals. The study involved the identification of five principals with exemplary interpersonal skills. Two different groups were asked to identify principals with exemplary interpersonal skills. Those identified by both groups formed the list from which five principals were selected and asked to participate in the study. The study involved in-depth interviews with the five principals. During the interviews the principals were asked about their personal and professional backgrounds. Questions about their professional background included topics such as degrees and majors, positions held in education, and length of time in education and in those positions. Their personal background included questions about their activities in high school and college, family, personality, and characteristics. Individual case analysis' were done on each interview and a cross-case analysis was done on all five interviews. The results of the study suggest that the principals' interpersonal skills were not developed through formal programs but over time and through their life experiences. Some of the factors that seemed to influence the principals' interpersonal skills include: activities that exposed them to the public, strong families, the positive impact of others, and similar personality or character traits. The study also produced some recommendations for further study, implications for principal preparation programs and lessons for principals to learn. / Ed. D.