The obser-view is a method to generate data and create a learning space for both researcher and participants in qualitative research. It includes reflection between the two after the researcher has observed the participant. This article aims to reveal the benefits and challenges encountered when using the obser-view in two different research projects. In a Dutch project whose aim was to empower residents with dementia, in nursing homes the obser-view was used to generate data and create space for reflection which included residents and the family members. It showed that the obser-view cannot be finished when reflection does not happen. A Danish project with the aim to map the practice for inmates’ opportunities for education and job guidance highlighted that it made participants—educational prison leaders and teachers—aware they were doing their jobs by rote and showed the difficulties the researcher had trying to reflect with some participants. In both projects the obser-view created a learning space for participants. A benefit of the obser-view is that it can be used in dissimilar settings with different research purposes and with vulnerable and stigmatized people often excluded from the research. A challenge is for the researcher to reflect with participants, which is more likely to be successful if they have had time to develop a trusting relationship. Although the obser-view is a novel method in qualitative research, it has proved useful in different settings. It is a valuable method and we recommend developing it further in additional different settings with different populations.