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While struggling to construct the meaning of their patients' experiences, therapists often feel confused by their patients' communications, driving them to elicit patterns of knowledge and intuitive rules, drawn from previous experiences, and to restore a sense of control. However, what is already known might affect the unknown, biasing the meaning of patients' communications, hence Bion's recommendation of therapists' attunement without memory and desire. The present article describes how supervisors can enhance their supervisees' ‘negative capability’, their tolerance of ambiguity and doubts, by illuminating specific countertransferential reactions in the form of heuristics that interrupt this capability. Heuristics, presented in the literature as potentially helpful mental devices, are examined in this article as possible disruptions to therapists’ meaning-making processes. However, heuristics in and of themselves are not negative or pathological phenomena. They are natural and spontaneous mechanisms, capable of temporarily reducing the anxiety of supervisees faced with ambiguous clinical situations. It is suggested that understanding the meaning of these phenomena might liberate supervisees from the need to respond impulsively and facilitate internal processes of metabolizing patients' experiences.