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.

People struggle with AI prompts because the model lacks background on their goals and progress. The solution is 'Context Engineering': creating an environment where the AI continuously accumulates user-specific information, materials, and intent, reducing the need for constant prompt tweaking.

Effective enterprise AI deployment involves running human and AI workflows in parallel. When the AI fails, it generates a data point for fine-tuning. When the human fails, it becomes a training moment for the employee. This "tandem system" creates a continuous feedback loop for both the model and the workforce.

Don't ask an LLM to perform initial error analysis; it lacks the product context to spot subtle failures. Instead, have a human expert write detailed, freeform notes ("open codes"). Then, leverage an LLM's strength in synthesis to automatically categorize those hundreds of human-written notes into actionable failure themes ("axial codes").

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.

Developers often test AI systems with well-formed, correctly spelled questions. However, real users submit vague, typo-ridden, and ambiguous prompts. Directly analyzing these raw logs is the most crucial first step to understanding how your product fails in the real world and where to focus quality improvements.

When a prompt yields poor results, use a meta-prompting technique. Feed the failing prompt back to the AI, describe the incorrect output, specify the desired outcome, and explicitly grant it permission to rewrite, add, or delete. The AI will then debug and improve its own instructions.

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.

When an AI model makes the same undesirable output two or three times, treat it as a signal. Create a custom rule or prompt instruction that explicitly codifies the desired behavior. This trains the AI to avoid that specific mistake in the future, improving consistency over time.