The present study discusses the mechanism and formalism of conversational planning. It is argued that the planner engages in a variety of metacognition as s/he perceives, interprets, evaluates, and produces cognitive actions that require careful attention and analysis. Following Flavell’s (1981) model of cognitive monitoring, a metacognitive model of conversational planning is proposed. The model consists of several cognitive and metacognitive components that are grouped into three categories: Causal Knowledge, Working Knowledge, and Conscious Experiences. Next, to elaborate the metacognitive components of the model, several examples of metacognitive variables in problem-solving situations are proposed. Then, focusing on these variables, the proposed model of conversational planning is illustrated using natural data taken from a clinical supervision session. In the last section, the relevance of the present study to pragmatics is briefly discussed with respect to mental operations involved in interpretation.