The main obstacle to deploying enterprise AI isn't just technical; it's achieving organizational alignment on a quantifiable definition of success. Creating a comprehensive evaluation suite is crucial before building, as no single person typically knows all the right answers.

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.

Instead of manually refining a complex prompt, create a process where an AI agent evaluates its own output. By providing a framework for self-critique, including quantitative scores and qualitative reasoning, the AI can iteratively enhance its own system instructions and achieve a much stronger result.

The frontier of AI training is moving beyond humans ranking model outputs (RLHF). Now, high-skilled experts create detailed success criteria (like rubrics or unit tests), which an AI then uses to provide feedback to the main model at scale, a process called RLAIF.

The primary bottleneck in improving AI is no longer data or compute, but the creation of 'evals'—tests that measure a model's capabilities. These evals act as product requirement documents (PRDs) for researchers, defining what success looks like and guiding the training process.

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.

You don't need to create an automated "LLM as a judge" for every potential failure. Many issues discovered during error analysis can be fixed with a simple prompt adjustment. Reserve the effort of building robust, automated evals for the 4-7 most persistent and critical failure modes that prompt changes alone cannot solve.

The prompts for your "LLM as a judge" evals function as a new form of PRD. They explicitly define the desired behavior, edge cases, and quality standards for your AI agent. Unlike static PRDs, these are living documents, derived from real user data and are constantly, automatically testing if the product meets its requirements.

OpenAI identifies agent evaluation as a key challenge. While they can currently grade an entire task's trace, the real difficulty lies in evaluating and optimizing the individual steps within a long, complex agentic workflow. This is a work-in-progress area critical for building reliable, production-grade agents.