Longitudinal academic advising (AA) and coaching programs are increasingly implemented in competency based medical education (CBME) to help residents reflect and act on the voluminous assessment data they receive. Documents created by residents for purposes of reflection are often used for a second, summative purpose--to help competence committees make decisions--which may be problematic. Using inductive, thematic analysis we analyzed written comments generated by 21 resident-AA dyads in one large internal medicine program who met over a 2 year period to determine what residents write when asked to reflect, how this aligns with what the AAs report, and what changes occur over time (total 109 resident self-reflections and 105 AA reports). Residents commented more on their developing autonomy, progress and improvement than AAs, who commented far more on performance measures. Over time, residents' writing shifted away from intrinsic roles, patient care and improvement towards what AAs focused on, including getting EPAs (entrustable professional activities), studying and exams. For EPAs, the emphasis was on getting sufficient numbers rather than reflecting on what residents were learning. Our findings challenge the practice of dual-purposing documents, by questioning the blurring of formative and summative intent, the structure of forms and their multiple conflicting purposes, and assumptions about the advising relationship over time. Our study suggests a need to re-evaluate how reflective documents are used in CBME programs. Further research should explore whether and how documentation can best be used to support resident growth and development.