The paper is an empirically based discussion of the relationship between multiple understandings of democracy with the multiple practices of evaluation. The conceptualization is inspired by three broad democratic evaluation orientations: elitist democratic evaluation, participatory democratic evaluation and discursive democratic evaluation as well as four dimensions of democracy (agency, voice, audience and influence). This paper is presenting the main results of three ethnographic research projects among school leaders in secondary education concerning evaluation practices and discourses. Using a critical ethnographic research methodology, the paper focuses on dilemmas, tensions and paradoxes of evaluation in an era of market driven accountability. A situated learning perspective has been applied in order to view evaluation as joint enterprises depending on shared vocabulary and repertoire of evaluative tools in each community of practice. Consequently, the relevance of the traditional dichotomies of evaluation is questioned based on the findings, and boundary objects are introduced as an alternative analytical tool. The school communities find themselves within an overall ideological and epistemological controversy between a drive for goal oriented and “evidence based” practices on one hand, and on the other hand the emancipative bottom up developmental strategies.