Utilizing organizational role theory and cognitive role theory as a theoretical framework, this phenomenological study examined the experience of parent-teachers and colleague-teachers in small educational settings and their perceptions of these dynamic relationships and potential areas of conflict. Findings highlighted perceived strengths, yet tensions and challenges persisted as teachers used a variety of management techniques to navigate their unique intrapersonal and interpersonal roles. Discussed are the themes that emerged from the data collected regarding role conflict, boundary crossing, boundary blurring, and management of the related tensions. The researchers argue that open communication concerning this phenomenon is important to improve a school's culture and organizational health. This study explored a small sample of voices at three small but distinct schools spanning early childhood through college level. The researchers believe this study begins a much needed dialogue about the impact parent-teachers in small school settings have on their respective school communities.