playbookintermediatecurrentAI Playbooks~1 min readVerified 2026-07-20#playbook#evaluation#datasets

Build an eval set from scratch

Mental model: an eval set is a compact executable contract for a product decision, not a scrapbook of prompts. Each case links an initial condition to expected behavior, an oracle, a slice, and an owner.

Mechanism: fixtures → oracle → release decision

Collect cases from production traces, experts, edge cases, and incidents; attach metadata and an end-state oracle; then run the same versioned fixtures before and after a change. Keep development, regression, and holdout splits separate so prompt tuning cannot become evaluation leakage.

case = {"id":"refund_missing_photo", "split":"holdout", "risk":"high", "oracle":"must_request_evidence"}
assert case["split"] != "dev" and case["oracle"]
print("case is protected from prompt tuning")

Run with python3; expected output is case is protected from prompt tuning.

Procedure

  1. State the user task, acceptance threshold, and prohibited failure.
  2. Collect 30–100 candidates and protect or remove sensitive data.
  3. Add task, language, domain, source, difficulty, risk, and authority metadata.
  4. Use deterministic checks where possible; calibrate rubrics and human samples otherwise.
  5. Include refusal, abstention, escalation, tool-error, and adversarial cases.
  6. Record quality, p95 latency, cost, and safety baseline; assign a refresh owner.
Requirement Check
Representative main workflows and known failures exist
Sliceable metadata supports segment analysis
Graded every case has oracle or rubric
Versioned fixtures and results reproduce
Governed owner, refresh trigger, privacy policy

Do not start with hundreds of random cases. Promote a change only when holdout quality, safety, and resource budgets clear their stated thresholds.

Exercises

  1. Create three negative cases where correct behavior is abstention.
  2. Add a failure trace to regression and specify its oracle.

Connects to: eval design · task evals · feedback loops

Sources