This article investigates whether CEOs actually demonstrate the communication strengths and weaknesses they think they have. Videotaped interviews with CEOs in the initial stage of executive coaching were analyzed to identify categories of communication strength and weakness: delivery, content, audience, and character. Next, the interviews and transcriptions were coded to track use of rhetorical formats, delivery stress, disfluencies, and timing. Speakers who identified themselves as having both delivery and content strengths or weaknesses differed significantly from the other CEOs. This has important implications for the study of impromptu communication, executive coaching, and business communication.