As the complexity of building and evaluating AI chatbots increases exponentially, a comprehensive framework is necessary for successful generative AI chatbot implementations. Conversation quality metrics are essential for measuring intelligence and reliability, while tool selection accuracy, intent detection, argument accuracy, and contextual requests pose significant challenges. The effectiveness of many AI chatbots heavily depends on their ability to retrieve and utilize external knowledge, with RAG metrics providing insights into retrieval accuracy and response generation quality. Knowledge cutoff awareness and domain boundary awareness ensure the chatbot maintains temporal and topical boundaries, while correctness metric focuses on factual accuracy in open-world statements. Task completion metrics measure a generative AI chatbot's core effectiveness, including task success rate, turn count, and resolution quality score. The journey of implementing and optimizing a generative AI chatbot is fundamentally about building trust from users, stakeholders, and the system itself, with successful organizations maintaining a balanced view across all metric categories while staying focused on their core business objectives.