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How would you evaluate an LLM application you've built?

Define task success, combine hard checks with supported-answer review, and make an evidence-limited release decision.

Published · 7 min read ·Role-specific ·Intermediate

Product & experimentation · active recall

Practice before you read

20 minutes. Define the decision first, then design the measurement and enumerate validity threats.

Product & experimentation · closed-book attempt

How would you evaluate an LLM application you've built?

Define the decision first, then design the measurement and enumerate validity threats.

Problem

Context. A document-answering application is assessed on held-out questions for valid citations and substantive source support. The invented counts and a predeclared joint-quality floor appear below. Task. Report each quality dimension, their intersection, cost, uncertainty, and the gate decision. Describe follow-up evaluation and online evidence needed before claiming product improvement. Constraints. Both quality requirements must hold on the same answer. Do not substitute citation validity for factual support or treat a small observed pass rate as a population guarantee. For 20 hypothetical held-out document questions, 18 answers cite valid IDs and 14 have independently human-reviewed substantive support. Thirteen satisfy both requirements; total cost is $0.40. The predeclared observed joint-quality floor is 70%. What should the report and release decision say?

20:00recommended time

Closing or reloading clears the scratchpad. Only score, weak rubric dimensions, attempt count, and retry date can be stored locally.

Reading depth

Define an LLM application’s release decision using task success, unacceptable failures, cost, and representative evidence.

Problem

Context. A document-answering application is assessed on held-out questions for valid citations and substantive source support. The invented counts and a predeclared joint-quality floor appear below.

Task. Report each quality dimension, their intersection, cost, uncertainty, and the gate decision. Describe follow-up evaluation and online evidence needed before claiming product improvement.

Constraints. Both quality requirements must hold on the same answer. Do not substitute citation validity for factual support or treat a small observed pass rate as a population guarantee.

For 20 hypothetical held-out document questions, 18 answers cite valid IDs and 14 have independently human-reviewed substantive support. Thirteen satisfy both requirements; total cost is $0.40. The predeclared observed joint-quality floor is 70%. What should the report and release decision say?

Picture

Citation syntax and semantic support are different checks; an answer must pass both. Five answers pass citation validation alone, one passes support alone, and one passes neither.

Separate checks, then combine requirements

Eighteen valid citation IDs and 14 supported answers yield 13 jointly valid answers.

Thirteen joint passes out of twenty miss the 70% release floor

Thirteen joint passes do not clear a fourteen-pass floorThirteen of twenty trials pass both requirements, or 65%. A 70% floor requires at least fourteen joint passes.The joint-pass floor counts actualtrial identities13/20 = 65%; required 14/20Outlined trial fourteen must alsobecome a joint pass.
Derivation
Thirteen joint passes fail the seventy-percent release floor Each of twenty tiles represents one hypothetical answer, grouped in one possible ordering. Thirteen tiles marked VS pass citation validity and support. Five marked V pass citation validity only, one marked S passes support only, and one dash passes neither. Thus eighteen pass validity, fourteen pass support, but only thirteen of twenty, or 65%, pass both. The joint-rate bar stops before the required 70% marker. Hold this candidate; the existing production version remains unchanged. Repair on development cases and use fresh independent confirmation. 20 hypothetical answers; one tile each VSVSVSVSVSVSVSVSVSVS VSVSVSVVVVVS- VS: 13 pass bothV: 5 citation only S: 1 support only-: 1 passes neither Joint pass rate 65% observed70% floor HOLD this candidate Existing production stays unchanged. Repair, then confirm on fresh cases.
count answers passing both requirements, not their average or union. Thirteen of twenty fails the 70% observed floor. Monitoring the existing production version does not authorize releasing this candidate.
Check: Does the illustrated candidate pass the stated gate? Which arrow shows what happens after it fails?
Read it this way: Thirteen of twenty trials pass both requirements, or 65%. A 70% floor requires at least fourteen joint passes.
Which single additional joint result is needed to reach seventy percent?

References: LLM-as-judge study, OpenAI evaluation guidance, and NIST AI RMF.

Report the joint outcome

SupportedUnsupportedTotal
Valid citation
Invalid citation
Total

Citation validity is 90%; support is 70%; joint validity is . Their arithmetic mean, 80%, is not the required success rate. The union is , which also answers a different question. Cost per jointly valid answer is dollars.

The observed joint floor fails. Report counts, sampling unit and an uncertainty method separately from this descriptive release rule. Twenty cases do not establish population quality; passing this floor would not prove improved user task completion.

Keep a case-level record

Record case_id, source/evidence version, slice, rubric, hard-check results, semantic labels, judge/model/prompt versions, latency and cost. Assign dataset ownership, review disagreements and preserve labels. Use deterministic checks for exact requirements and qualified humans to validate open-ended scoring.

Change the output or severity

1. Require a structured record

New task: the answer must satisfy an exact schema and field constraints.

Picture and change: validate parseability, types and constraints deterministically before semantic grading.

Check: malformed output fails its hard gate despite supported prose.

Use when: the consumer depends on an exact output contract.

2. Increase failure severity

New task: answers concern medication instructions.

Picture and change: add expert review, harmful-error slices, abstention and a governed release process.

Check: routine successes cannot compensate for a prohibited harmful answer.

Use when: errors can create high-impact harm; this example provides no domain validation.

Failure and transfer

After tuning prompts on these final cases, later scores become development evidence, not independent confirmation. Keep fresh confirmation data separate from rubric repair.

Is easy-question judge agreement enough when unsupported legal claims are missed?

Check your answer

No. Validate the consequential slice and route unreliable cases to qualified humans or abstention.

A metric list is incomplete

BLEU, ROUGE, METEOR and perplexity measure particular properties, not every product’s task success. Public benchmarks can supplement product-specific evidence, not replace it.

Cases and scorer validation

Stratify representative traffic and known failure slices. Size the set for coverage and uncertainty needs, not a universal 50–200-example rule. Check scorer mistakes by slice, not agreement alone. Chance-corrected agreement can complement, not replace, consequential-error analysis.

Lifecycle and tradeoffs

Test judge sensitivity to position, verbosity, model family and domain gaps. Pairwise comparisons can help; counterbalance order and validate their reliability. Bradley–Terry ranking introduces assumptions, not guaranteed agreement.

Version scorer changes and retest against humans. Measure quality, latency and cost jointly; inspect nondominated choices rather than optimizing a score alone. Track user task completion, corrections or feedback with suitable denominators. No universal offline-online correlation cutoff certifies an evaluation.

Inspectable reasoning

State task, costly failures, evidence limits and the decision each measurement supports. Use only truthful experience; no answer guarantees a hiring outcome.

Avoid unsupported certainty

A judge prompt is not calibration, and aggregate quality can hide consequential regressions.

Scope the answer

Explain what the system must do, how errors are checked and who owns evaluation changes.

Read the long-form essay this distills: “LLM Evals: The hardest part of shipping LLMs”.