This guide outlines six key considerations for healthcare leaders when selecting a conversational AI partner. It begins by emphasizing the importance of specific, verifiable use cases tailored to healthcare needs. The document details the necessity of confirming technical compatibility and integration with existing systems, particularly electronic health records (EHR). It also discusses the operational readiness required for EHR systems to effectively incorporate conversational AI capabilities. Additionally, the guide highlights the significance of preconfigured use cases that can be prioritized for implementation. Cost considerations are addressed, including potential variable charges associated with AI services. Finally, the guide underscores the importance of performance guarantees and compliance with security regulations, such as HIPAA, ensuring that selected vendors meet necessary privacy and security standards. Overall, this document serves as a comprehensive resource for healthcare organizations navigating the selection process for conversational AI solutions.