This article introduces a novel Dynamic Conversational AI Coach that works side‑by‑side with security and compliance teams while they fill out vendor questionnaires. By blending natural‑language understanding, contextual knowledge graphs, and real‑time evidence retrieval, the coach reduces turnaround time, improves answer consistency, and creates an auditable dialog trail. The piece covers the problem space, architecture, implementation steps, best practices, and future directions for organizations looking to modernize questionnaire workflows.