The investigation reported on here was designed to determine the common demands of the position of headmaster as distinct from the unique individuality of the headmaster personality. The first part of the presentation draws its information from current literature and attempts to set down the theoretical bases of the headmastership. The literature points to certain desirable personal characteristics and leadership qualities, including basic managerial skills and dedication to the educational process and to individual needs. It stresses the need to understand the individuality of each group affected by the school; i.e., students, faculty, staff, parents, trustees, alumni, community members, and an employee and his dependents. Related documents are ED 071 177-78 and headmasters should be capable of fulfilling the various roles of change facilitator, financial manager, decision coordinator, educational enthusiast, communicator, and evaluator. The second part of the report presents the results of a questionnaire sent to a select group of practicing headmasters. Some of the conclusions derived from the findings indicate that (1) headmasters wish to spend considerably more time conferring with faculty, students, and parents, but not with trustees; (2) the activities of improving instruction and evaluating were performed less frequently than desired; (3) most independent school headmasters have had relatively little experience in public schools; and (4) general experiences in graduate schools are the least helpful in preparing headmasters for their leadership roles. (Author/WM)