The present study analyzes how role conflict, or distress or negative sentiments about tutoring work, are expressed in tutor post-session notes. Through corpus and linguistic analysis of session notes, researchers found that role conflict was not only present in many session notes–especially from tutors with more training and experience–but it often resulted from tutors’ feelings of powerlessness, time limitations, or other constraints around their work. In analyzing session notes’ linguistic features, we focused on hedging and boosting, or any words which reduce or amplify certainty in speech respectively (Lakoff, 1973). From this, we identified distinct “communication identities” among tutors wherein those who reported positive outcomes in tutoring work often using boosting language, and those who reported negative experiences used hedging language. Tutors overwhelmingly relied on hedging and non-constructive language to articulate role conflicts in their session notes, which suggests a discomfort with directly addressing work-related conflict. We found that tutors gravitate towards indirect politeness strategies (such as hedging) to discuss conflict in their work which paradoxically hinders their reflective processes and forestalls more meaningful engagement with conflict in professionalization contexts. This paper provides alternative and more generative ways to talk about role conflict, politeness strategies, and tutor work identities. Keywords : Writing Center, Session Notes, Politeness, Role Conflict, Linguistic Analysis