When deploying AI tools, especially in sales, users exhibit no patience for mistakes. While a human making an error receives coaching and a second chance, an AI's single failure can cause users to abandon the tool permanently due to a complete loss of trust.

Consumers can easily re-prompt a chatbot, but enterprises cannot afford mistakes like shutting down the wrong server. This high-stakes environment means AI agents won't be given autonomy for critical tasks until they can guarantee near-perfect precision and accuracy, creating a major barrier to adoption.

AI models show impressive performance on evaluation benchmarks but underwhelm in real-world applications. This gap exists because researchers, focused on evals, create reinforcement learning (RL) environments that mirror test tasks. This leads to narrow intelligence that doesn't generalize, a form of human-driven reward hacking.

Generic evaluation metrics like "helpfulness" or "conciseness" are vague and untrustworthy. A better approach is to first perform manual error analysis to find recurring problems (e.g., "tour scheduling failures"). Then, build specific, targeted evaluations (evals) that directly measure the frequency of these concrete issues, making metrics meaningful.

Standardized benchmarks for AI models are largely irrelevant for business applications. Companies need to create their own evaluation systems tailored to their specific industry, workflows, and use cases to accurately assess which new model provides a tangible benefit and ROI.

Treating AI evaluation like a final exam is a mistake. For critical enterprise systems, evaluations should be embedded at every step of an agent's workflow (e.g., after planning, before action). This is akin to unit testing in classic software development and is essential for building trustworthy, production-ready agents.

Traditional product metrics like DAU are meaningless for autonomous AI agents that operate without user interaction. Product teams must redefine success by focusing on tangible business outcomes. Instead of tracking agent usage, measure "support tickets automatically closed" or "workflows completed."

The common mistake in building AI evals is jumping straight to writing automated tests. The correct first step is a manual process called "error analysis" or "open coding," where a product expert reviews real user interaction logs to understand what's actually going wrong. This grounds your entire evaluation process in reality.

Do not blindly trust an LLM's evaluation scores. The biggest mistake is showing stakeholders metrics that don't match their perception of product quality. To build trust, first hand-label a sample of data with binary outcomes (good/bad), then compare the LLM judge's scores against these human labels to ensure agreement before deploying the eval.