Skip to content
The AI Tech Lead Path
The path
0515 min read · 200 XP

Evaluation & eval-driven development

The keystone skill. Own this and you own quality.

0%

If you can prove an AI system is good and catch when it regresses, you own quality — and quality is your authority across teams. Most teams can't do this. Make evals the heartbeat of every AI feature, including your own AI-SDLC pipeline.

Key ideas

  1. 1

    Eval-driven development: define how you'll measure success BEFORE building, then iterate against it — like test-driven development for AI.

  2. 2

    Start with error analysis: read real outputs, label failure modes, and let those define your metrics. Don't start from generic benchmarks.

  3. 3

    Build a golden dataset of representative inputs with expected behavior; run it in CI so a prompt/model change that regresses fails the build.

  4. 4

    LLM-as-judge scales evaluation but has pitfalls (bias, inconsistency) — calibrate judges against human labels and prefer pairwise comparisons for subtle quality.

  5. 5

    Combine offline evals (regression suites) with online signals (A/B tests, guardrail metrics, human feedback) from production.

How to start (this week)

  • Collect ~50–100 real inputs covering the important cases and edge cases.
  • Read outputs and do error analysis: cluster failures into named categories.
  • Turn the top failure categories into checks (assertions, rubrics, or judge prompts).
  • Wire it into CI; track scores over time; gate risky changes.

Metrics that fit the task

  • RAG: retrieval recall/precision, faithfulness/groundedness, citation accuracy.
  • Classification/extraction: precision/recall/F1 against labels.
  • Generation/agents: task success rate, rubric scores, pairwise win-rate vs a baseline.
  • Always track cost and latency alongside quality.

Watch

Why AI evals are the hottest new skillHamel Husain & Shreya Shankar
LLM Evals: common mistakesShankar & Husain

Do the work

0/5 · 0%

Test yourself

Question 1 / 4

What's the best STARTING point for building evals?

27 chapters · progress saves automatically