Members of the trustee boards of the 15 Massachusetts community colleges are appointed by the Governor to provide the fiscal and policy oversight for their colleges and help shape and align a vision and mission for the colleges in partnership with the college's president. Trustees, however, as revealed in the literature and in the research data, often come to their governance role unprepared or with a lack of understanding about their roles. This qualitative study, employing the phenomenological approach and the theoretical frameworks used in organizational behavior, allowed this researcher to interview three groups of community college participants experienced with trustee orientation and development in Massachusetts. In searching for the answers to the study's two research questions, "How could a comprehensive orientation and development program of Board of Trustees' members lead to a clear understanding of the role of trustees vis-à-vis the institution and improve the working relationship with the college president and other leaders within the college?" and "How could an ongoing, statewide orientation program be developed to promote training consistency for the boards of trustees of the 15 Massachusetts community colleges or how could each college individualize its own orientation program for trustees?", this researcher was able to gauge presidents', trainers', and trustees' perspectives on the value, nature, and design of the orientation and development phenomena and in fostering a clear understanding of appropriate trustee roles. The study also examined whether a statewide orientation/development program might be valuable in providing training consistency amongst colleges. Variances emerged in the value of different subjects to be included in orientation and development programs and in those that were deemed most effective. The recommendation of the study include the importance of community college trustee training, conducted in both a local and system-wide, but not state-wide manner, as being essential for a community college's successful operation.