Insights from Real Evaluation Work

Most teams test AI agents with demo prompts and hope for the best. Here's the framework I use to systematically find failure modes across 78 multi-step scenarios before a single user touches the product.

Your AI demo looks amazing. Your production users are furious. The gap between demo performance and real-world reliability is where most AI products die. Here's what I learned testing GPT-5.1, Claude 4.5, and Gemini 3 Pro.

We built an LLM-as-a-Judge system processing 100K+ evaluations daily with 0.89 Spearman correlation to expert labels. Here's what we learned about when automated judges are reliable and when they're dangerously wrong.