Supervising learners as they communicate often places faculty preceptors in a classic educational dilemma. What should a preceptor do when the learner is not communicating well and is not asking for help? What usually happens, in the authors' experiences, is that the preceptor decides at some point that she or he cannot stand the situation anymore-then interrupts the learner and takes over the conversation. Interrupting in this way, however, comes at the cost of undermining the learner. Thus, the authors have developed an alternative teaching strategy designed for communication tasks such as giving serious or bad news. In the strategy recommended here, the preceptor sets up the possibility that he or she may intervene in the encounter. If the preceptor does intervene, he or she explicitly hands the conversation back to the learner and afterwards debriefs with the learner. The authors designed this strategy to decrease the risk to the patient while maximizing learning for the learner. This strategy offers preceptors a way to teach communication skills more effectively in clinical settings using intentional goal setting with learners, careful observation of the encounter, intervention when the conversation is not going well, and reflective feedback for the learner based on the learner's goals.