This article presents preliminary findings on an investigation into the differences in communicative performance across varying speaking conditions, of an individual with a cognitive–linguistic impairment following traumatic brain injury (TBI). The article compares the communicative exchanges of an individual in a conversation with a therapist, a conversational dyad with a peer with TBI, and in a communication group task where they were interacting with other participants with TBI. The speaking conditions studied included an unstructured chat, the participant requesting information and the participant giving information. Results showed that the person with TBI responded to differences in communication partner and speaker role. He was best able to give information in the unstructured chat with the clinician and the information giving session in the group. Requesting was maximally facilitated in the information request condition with the clinician. Qualitatively, however, the most equal interactions occurred with the peer, with evidence of the person with TBI engaging in typical conversational strategies such as establishing common ground to facilitate topic development and co-constructing the discourse topics. These strategies did not occur in the clinician or group interactions, possibly due to power imbalance in the former and impaired cognitive–linguistic ability in the latter situation. Implications for clinical decision making regarding intervention strategies for patients with cognitive–communication deficits are discussed.