Those rare moments when clients ask direct questions of their therapists likely represent a point when they are particularly open to new considerations, thereby representing an opportunity for substantial therapeutic gains. However, clinical errors abound in this area because clients’ questions often engender apprehension in therapists, causing therapists to respond with too little or too much information or shutting down the discussion prematurely. These response types can damage the therapeutic relationship, the psychotherapy process, or both. We explore the nature of these clinical errors in response to client questions by providing examples from our own clinical work, suggesting potential reasons why clinicians may not make optimal use of client questions, and discussing how the mixed psychological literature further complicates the issue. We also present four guidelines designed to help therapists, trainers, and supervisors respond constructively to clinical questions in order to create constructive interactions.