The present study explores the dilemmas and related coping strategies teachers experience as part of their work with individual development plans (IDPs) in Sweden. Through qualitative content analysis of 15 interviews with Swedish elementary school teachers, the dilemmas and coping strategies were identified and analysed. From an activity theory point of view, dilemmas are seen as discursive manifestations of contradictions that exist within the activity system of instruction. The IDP dilemmas are interpreted as emerging from a central contradiction between trust in teachers' professionalism vis-à-vis external steering and control. The three defined dilemmas are identified as involving time use (documentation vs. instruction), communication (officially correct language vs. pupil-friendly language) and type of assessment (summative vs. formative). Moreover, three qualitatively different dilemma management strategies were discerned.