The key to creating effective and reliable AI workflows is distinguishing between tasks AI excels at (mechanical, repetitive actions) and those it struggles with (judgment, nuanced decisions). Focus on automating the mechanical parts first to build a valuable and trustworthy product.

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.

When using an LLM to evaluate another AI's output, instruct it to return a binary score (e.g., True/False, Pass/Fail) instead of a numbered scale. Binary outputs are easier to align with human preferences and map directly to the binary decisions (e.g., ship or fix) that product teams ultimately make.

Building a functional AI agent is just the starting point. The real work lies in developing a set of evaluations ("evals") to test if the agent consistently behaves as expected. Without quantifying failures and successes against a standard, you're just guessing, not iteratively improving the agent's performance.

Don't aim for a 100% accurate evaluation system. A good system reveals a 'healthy percentage' of incorrect outputs. Getting excited when evals are wrong is key, as each failure is a clear, actionable opportunity to improve your AI agent.

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.

When creating an "LLM as a judge" to automate evaluations, resist the urge to use a 1-5 rating scale. This creates ambiguity (what does a 3.2 vs 3.7 mean?). Instead, force the judge to make a binary "pass" or "fail" decision. It's a more painful but ultimately more tractable and actionable way to measure quality.

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.

Many people struggle to define what 'good' looks like. Building an evaluation (eval) for an AI system requires you to codify your quality standards, forcing a level of clarity and commitment that improves your own process and the AI's output.