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Sach1ngSach1ng/PM-operating-OS/skills/eval-brief/SKILL.md

eval-brief

Skill3 starsChanged 18 days agoMITView on GitHub

Design evals as the definition of done for an AI surface. Use when the user says eval, golden set, quality bar, LLM-as-judge, acceptance criteria for an agent, or "how do we know this is good enough to ship.

The file

We split this skill into the rules it gives an agent

7 rules. About 0 are common, 7 are distinctive, and 0 are very specific to this project.

  • ≈0

    Common · estimate

    Many files like this have a rule of this kind.

  • ≈7

    Distinctive · estimate

    This author's own choices. Worth a look.

  • 0

    Very specific

    Tied to their project's names, files or tools. Probably skip.

  • Common
  • Distinctive
  • Very specific
  1. Distinctive:

    After a production miss (add the miss to the set)

    line 15
  2. Distinctive:

    Default set for most copilots:

    line 25
  3. Distinctive:

    Add latency/cost if the job is interactive or loops.

    line 34
  4. Distinctive:

    If PM and eng disagree on labels, the eval is the product conversation.

    line 55
  5. Distinctive:

    Do not wait for a platform.

    line 65
  6. Distinctive:

    When production fails, add a case the same day.

    line 67
  7. Distinctive:

    Never use "helpfulness" as the only dimension.

    line 68

≈ “Common” is an estimate: at least 1 in 5 of the 350,495 skill files we read have a rule of the same kind, not the same words. “Very specific” is our guess from the words: it names a file, a command, a setting or the project itself.

Keep what fits and drop the rest. Your version, ready for your agents.
Files
SKILL.md

Eval Brief

Turn "the AI should be good" into a testable quality bar. For AI surfaces, evals are acceptance criteria — not a later QA step.

When to use

  • New AI feature or agent job
  • Prompt, model, tool, or retrieval change
  • "What does done mean?" on an LLM surface
  • After a production miss (add the miss to the set)

Process

1. Name the jobs

List end-to-end jobs, not model capabilities. One row per job: user, done looks like, forbidden.

2. Pick 3–5 dimensions

Default set for most copilots:

DimensionWhy
FaithfulnessDid it invent facts?
BoundaryDid it take a forbidden action?
UsefulnessDid it complete the job?
Failure honestyDid it admit unknowns?

Add latency/cost if the job is interactive or loops.

3. Build a small set from reality

Start with ~20 cases:

  • Golden (ideal)
  • Edge (missing evidence, conflict)
  • Adversarial ("just make up a number")
  • At least one real production miss, as soon as you have one

A pass is evidence about known failures. It is not a claim of general quality.

4. Choose judges you can afford

JudgeUse for
Heuristic / regex / tool-traceBoundaries, schema, forbidden tools
LLM-as-judgeFaithfulness, tone — calibrate on human labels
HumanDisagreements and new failure modes

If PM and eng disagree on labels, the eval is the product conversation. Resolve it before scaling the judge.

5. Write the brief

Save to knowledge/products/<product>/evals.md. If the file does not exist, copy knowledge/products/_template/evals.md.

Also log a decision if this eval gates a ship or blocks autonomy.

Rules

  • Do not wait for a platform. A spreadsheet is a valid v1.
  • Re-run on every prompt/model/tool/context change.
  • When production fails, add a case the same day. That is the improvement loop.
  • Never use "helpfulness" as the only dimension.
  • Claims in launches and sales must match the last eval run (date + conditions).

Output

A filled evals.md plus, if asked, a 10-case starter table the user can label this week.

Download now (ZIP)

Does it work?

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  • It worked
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  • It didn't
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Your trail

Files you open will collect here, so you can find them again.

Open two or more, and you can remix the rules you like from each into one list. Kept in this browser only.

Now do this for your own.

Bring your CLAUDE.md, AGENTS.md or skills. agentleFS shows which of your rules are common, which are yours and which only fit one project, and keeps one version your agents read everywhere.