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πŸ§ͺLearn to Evaluate LLM Outputs Systematically

Move from eyeballing LLM outputs to running a CI eval that blocks regressions on a real prompt. You'll build a 20-item dataset, write a binary rubric, calibrate LLM-as-judge, and ship the harness in your repo.

Applied14 drops~2-week path Β· 5–8 min/daytechnology

Phase 1Why 'looks good' isn't an evaluation

See why vibes-based testing hides real regressions

3 drops
  1. Vibes are not an evaluation method

    6 min

    Vibes are not an evaluation method

  2. False confidence and false alarms hurt differently

    6 min

    False confidence and false alarms hurt differently

  3. Anecdotes lie; distributions don't

    7 min

    Anecdotes lie; distributions don't

Phase 2Building your first eval set and rubric

Build your first 20-item eval set and rubric

4 drops
  1. Collect twenty real inputs before you write any rubric

    7 min

    Collect twenty real inputs before you write any rubric

  2. Binary rubrics force the question 'what counts as success?'

    7 min

    Binary rubrics force the question 'what counts as success?'

  3. Write golden outputs to lock in your taste

    7 min

    Write golden outputs to lock in your taste

  4. If two humans disagree, the rubric is broken β€” not the humans

    7 min

    If two humans disagree, the rubric is broken β€” not the humans

Phase 3Reference-free scoring and LLM-as-judge

Use LLM-as-judge and pairwise scoring without bias

3 drops
  1. When a teammate proposes 'just check if it sounds right'

    7 min

    When a teammate proposes 'just check if it sounds right'

  2. Your judge prefers verbose, formal answers β€” even when they're wrong

    8 min

    Your judge prefers verbose, formal answers β€” even when they're wrong

  3. The new prompt scores higher β€” but only on easy items

    8 min

    The new prompt scores higher β€” but only on easy items

Phase 4Shipping a CI eval for your prompt

Wire a CI eval that blocks regressions

4 drops
  1. Set up the eval harness as code, not a notebook

    8 min

    Set up the eval harness as code, not a notebook

  2. Add an LLM-as-judge layer with calibration

    8 min

    Add an LLM-as-judge layer with calibration

  3. Wire the eval into CI so it runs on every PR

    8 min

    Wire the eval into CI so it runs on every PR

  4. Document the eval and schedule the dataset refresh

    8 min

    Document the eval and schedule the dataset refresh

Frequently asked questions

How do you evaluate LLM outputs without a ground-truth answer?
This is covered in the β€œLearn to Evaluate LLM Outputs Systematically” learning path. Start with daily 5-minute micro-lessons that build from fundamentals to hands-on application.
What makes LLM-as-judge biased and how do you correct for it?
This is covered in the β€œLearn to Evaluate LLM Outputs Systematically” learning path. Start with daily 5-minute micro-lessons that build from fundamentals to hands-on application.
How big does an eval set need to be to catch regressions?
This is covered in the β€œLearn to Evaluate LLM Outputs Systematically” learning path. Start with daily 5-minute micro-lessons that build from fundamentals to hands-on application.
What's the difference between offline evals and CI evals?
This is covered in the β€œLearn to Evaluate LLM Outputs Systematically” learning path. Start with daily 5-minute micro-lessons that build from fundamentals to hands-on application.
When should you use pairwise preference instead of a rubric?
This is covered in the β€œLearn to Evaluate LLM Outputs Systematically” learning path. Start with daily 5-minute micro-lessons that build from fundamentals to hands-on application.