The purpose of this qualitative case study was to gain insight into the perspectives of experienced higher education administrators regarding faculty unionization, the collective bargaining process, and the interpersonal relationships between higher education faculty members and administrators. The primary method of data collection was semi-structured face to face interviews with nine administrators from two community colleges and two universities in the south Florida area. All of the study participants worked with unionized faculty members and had direct experience participating in bargaining negotiations. Upon the completion of each interview, the researcher listened to the taped audio recording of the interview several times and then transcribed all of the information from the audiotape into a Word file. Data collection and analysis for each participant were performed concurrently. Using a modified concept mapping approach, the research questions were written on large yellow sticky notes and placed in the middle of a wall in the researcher’s home with nine descriptive categorical themes written on smaller sticky notes placed around the study questions. The highlighted quotes and key phrases were cut from each transcript and placed under each of the descriptive categories. Over the course of a few months repeatedly reviewing the research questions that guided this study, the theory of symbolic interactionism, and relevant literature the categorical descriptive themes were refined and condensed into five descriptive themes. Study findings indicated that the administrators: (a) must have a clear understanding of what it is that the faculty does to be an effective representative at the bargaining table, (b) experienced role ambiguity and role strain related to a lack of understanding as to their role at the bargaining table and a lack of organizational support, (c) were not offered any type of training in preparation for bargaining, (d) perceived a definite “us versus them” mentality between faculty and administration, and (e) saw faculty collective bargaining at public institutions of higher education in Florida as ineffectual.