This document is a checklist designed for evaluating AI tools to distinguish those that provide sustainable value from those that may lead to costly issues. It can be utilized during vendor assessments, pilot planning, and post-deployment reviews. The checklist comprises critical decision factors derived from a comprehensive evaluation framework. Each item addresses specific aspects such as strategic alignment, use case definition, data and risk management, technical integration, workflow and adoption, pilot validation, financial justification, vendor partnership, and scaling and governance. The document emphasizes the importance of gathering stakeholder input, assessing organizational readiness, defining use cases, ensuring data quality and compliance, and establishing a governance structure for AI implementation. It serves as a practical guide for organizations to navigate the complexities of AI tool evaluation and integration effectively.