The present article focuses on the study of circular questioning “in situ,” that is, in the context of the discursive arena of an actual first systemic family therapy session. Two typical circular questions are selected, and discourse analysis heavily drawing from the discursive action model is deployed with the aim to highlight their function in the context of therapist and family members' problem talk. The analysis demonstrates the gradual building of two respective patterns, which both exhibit signs of shifts toward the instillment of a systemic epistemology in relation to problem talk: a shift from homogeneity to heterogeneity in family members' voices, which legitimizes the existence of different viewpoints within a system, and a shift from the construction of an accusation toward its deconstruction, which challenges the linear perception of causality underlying the accusation, thus introducing a more circular perspective. Implications are discussed in relation to contemporary, constructionist systemic family therapy practice, and reference is made to the methodological “promises” and challenges of the deployment of discourse analysis for the scrutiny of systemic family therapy therapeutic techniques and tools under a discursively informed light.