Evals are the most underrated skill in AI engineering.
1. Start with error analysis, not metrics
Sample 100+ production traces. Annotate each failure in free text (open coding), then cluster them into failure categories (axial coding). Count frequency per category. Your top 3 categories are your first metrics.
2. Build a versioned golden dataset
Store inputs, expected outputs or rubrics, and metadata (intent, difficulty, user segment) in a versioned dataset. Stratify it so rare but critical cases aren't drowned out by easy ones. Version it alongside your prompts so every score is reproducible.
3. Generate synthetic data along explicit dimensions
Don't just ask an LLM for "test questions." Define dimensions (persona × intent × complexity × edge case), generate combinations as tuples, then turn each tuple into a natural input. You get coverage instead of 200 near-identical examples.
4. Deterministic assertions first
JSON schema validation, regex checks, required fields, length limits, code execution, SQL that actually runs against a test DB. These are cheap, fast, and have zero variance. Reserve model-based grading for what code genuinely can't check.
5. Evaluate retrieval separately from generation
For RAG, measure retrieval with recall@k, MRR, or nDCG against labeled relevant chunks. Measure generation with faithfulness (is every claim supported by retrieved context?). If you only score the final answer, you can't tell which half is broken.
6. Trajectory evals for agents
Log every step: tool name, arguments, result, tokens. Score tool-call precision and recall against a reference path, argument correctness, step count, and error recovery. An agent that reaches the right answer in 14 calls when 3 would do is a cost and latency bug.
7. pass@k vs pass^k
pass@k = succeeded at least once in k runs. pass^k = succeeded in all k runs. At 80% per-run success, pass^5 drops to roughly 33%. Production reliability lives in pass^k, so run each case multiple times at your real temperature.
8. Simulated users for multi-turn
Give an LLM a persona, a hidden goal, and constraints, then let it converse with your system until the goal is met or a turn limit hits. Grade goal completion, turns-to-resolution, and policy violations. Single-turn evals miss most state and memory bugs.
9. Align your LLM judge like a classifier
Hand-label 100+ examples as pass/fail. Split into train/dev/test. Iterate on the judge prompt using dev, then report TPR and TNR on test. Use binary outputs with a written rubric, require a short critique before the verdict, and pin the judge model version.
10. Control judge bias in pairwise comparisons
LLM judges have position bias and often prefer longer answers. Run every A/B comparison twice with swapped order and only count consistent verdicts. Normalize or cap length if verbosity is skewing results.
11. Respect statistics
With 100 examples at 80% accuracy, your 95% confidence interval is about ±8 points. A jump from 80% to 83% is probably noise. Use bootstrapped confidence intervals, or a paired test on the same examples, before declaring a win.
12. Gate deploys in CI
Run the eval suite on every PR that touches prompts, models, tools, or retrieval config. Set per-category thresholds instead of one global score, so a big win in one area can't hide a regression in another. Fail the build on a regression.
13. Online evals in production
Sample a percentage of live traffic, run your judges asynchronously, and alert on drift per failure category. Use shadow deployments to run a new prompt or model on real traffic without showing users the output.
14. Make cost and latency first-class metrics
Track tokens per request, cost per successful task (not per call), and p50/p95 latency next to quality. A change that keeps quality flat while cutting cost 40% is a real win and deserves to ship.
15. Close the loop
Every production failure becomes a new labeled test case. Every new model release gets run against the full suite before anyone debates switching. Over time your eval set becomes the most valuable asset in the codebase.
Prompts are disposable. Models get replaced every few months.
Your eval infrastructure is what compounds.
