We would like to introduce you to the rather delicate and ambiguous topic of assessing reflection: on the one hand assessments are a valid tool for tracking the learning process of learners, but on the other hand we’ve experienced in our partner organizations how assessments can have an often underestimated negative impact on the quality of reflection. In this chapter we want to explore how to deal with assessment of reflection in an alternative way, questioning even the possibility to assess reflections (especially in the case of exposing personal feelings and experiences).