During the period 1990-1991, a study was conducted of 13 deans and directors of continuing education who were in the first 3 years of their new positions. This group of newer deans and directors included some who were promoted to the position for the first time as well as those who had transferred from one deanship/directorship to another. The study identified factors that led to "easier" and "harder" transitions to the dean's or director's position and also how aspects of the job of leading a continuing education unit appear to change over time. The main determining factors for transitions seemed to be a familiarity with and understanding of the institution, experience in the director's role, and the value placed on continuing education at that institution. Directors having an"easier" transition had knowledge of the institutions, experience in the director's role, and were working in institutions in which continuing education was respected. The "outsiders," deans who were brought in from other institutions, were more experienced, had a broader sense of strategy, greater self-confidence, a stronger commitment to continuing education, and higher perceptions of support from the instituion than those who had been promoted. The paper recommends follow-up research at a later date to see if the "newness" advantage of the "outsiders" had worn off after 3 years. (11 references) (Author/KC)