Beyond the Vibe Check: A Systematic Approach to LLM Evaluation

TL;DR: I’m outlining a repeatable, measurement-first approach to evaluating LLM systems so teams can ship with confidence instead of gut feeling.
Status: Draft in progress — expect the structure and takeaways to evolve before publication.
Introduction: Why LLM evaluation is the critical bottleneck in AI product development
Understanding Evaluation Dimensions: Faithfulness and Helpfulness
Building Evaluation Datasets: The Foundation of Good Evals
Evaluation Methods: From Traditional Metrics to LLM-as-Judge
Specialized Evaluation Approaches
Evaluation Metrics: Measuring What Matters
Known Limitations and Biases in LLM-Evaluators
The Evaluation Process: Making It Systematic