Eval Suite Design

You are designing an evaluation suite for an AI product feature — a systematic set of tests that catches real failure modes before they reach users. The goal is a suite that the team actually runs and acts on, not one that gets ignored.

Framework: Hamel Husain + Shreya Shankar (Building eval systems, 2025), Aman Khan (Beyond vibe checks, 2025).

Key principle: "Evals quietly decide whether your AI product thrives or dies. The ability to write great evals is rapidly becoming the defining skill for AI PMs in 2025 and beyond." — Aman Khan, Lenny's Newsletter (2025)

Step 1 — Load Context

Read the error analysis output (from the error-analysis skill or user input) to understand which failure categories to target. Read memory/user-profile.md for the AI feature context.

Step 2 — Three Types of Evals

For each failure category, select the appropriate eval type:

Type 1 — Code-based evals (deterministic): Best for: Failures with objectively correct / incorrect answers. Format compliance. Structural checks. Examples:

• Output contains required sections (assert "## Problem" in output)
• Output is within length bounds (assert len(output) < 2000)
• Output is valid JSON (try parse; fail if exception)
• Required fields are non-empty (assert output.get('metric') is not None) Pros: Fast, cheap, perfectly reliable Cons: Only works for objective correctness — can't evaluate quality

Type 2 — Human evals: Best for: Subjective quality, domain-specific correctness, complex reasoning, new failure categories being discovered. Format: Annotators see (input, output) pairs and rate: Thumbs up / Thumbs down, or score on a rubric (1–5). Pros: Highest accuracy; catches nuanced failures Cons: Slow, expensive, can't scale; requires clear annotation guidelines Use for: Calibration, sampling for quality assurance, training LLM-as-judge

Type 3 — LLM-as-judge: Best for: Subjective quality at scale; failures that require reasoning to detect; when human evals are too slow. Structure: A separate LLM (usually a stronger model) reviews (input, output) pairs and provides a judgment. Pros: Scalable; can evaluate complex quality; can explain its reasoning Cons: Not perfectly reliable; needs calibration against human evals; can be biased

Step 3 — Eval Design Per Failure Category

For each top failure category (from error analysis):

Name: [Failure category name] Eval type: [Code-based / Human / LLM-as-judge] What to test: [Specific aspect of the output being evaluated] Test cases needed: [How many? Where do they come from?] Pass/fail criteria: [What counts as pass? What counts as fail?] Automation plan: [When does this eval run — on every PR? Daily? Weekly?]

Step 4 — LLM-as-Judge Prompt Design

If using LLM-as-judge, write the judge prompt following best practices:

You are evaluating an AI assistant's response for [failure type].

**Input to the AI assistant:**
{input}

**AI assistant's response:**
{response}

**Evaluation criteria:**
[Criterion 1]: [Clear definition of what good looks like]
[Criterion 2]: [Clear definition of what good looks like]

**Scoring:**
- PASS: The response [specific pass condition]
- FAIL: The response [specific fail condition]

**Your output:**
First, briefly explain your reasoning (1–2 sentences).
Then output: PASS or FAIL

Key principles for judge prompts:

• Binary outputs (PASS/FAIL) are more reliable than numeric scores
• Include examples of PASS and FAIL in the prompt when possible
• The judge should explain its reasoning before giving the verdict (chain-of-thought)
• Calibrate the judge against 50+ human annotations before trusting it

Step 5 — The Principal Domain Expert Model

From Hamel Husain: designate one "benevolent dictator" for quality — one person whose judgment defines what PASS/FAIL means for subjective evals. This prevents annotation conflicts and anchors the LLM-as-judge calibration.

This person:

• Reviews 50–100 human annotation cases to establish the quality bar
• Resolves disagreements between annotators
• Periodically reviews LLM-as-judge outputs to catch drift

Step 6 — Eval Suite Structure

Design the full suite as three layers:

Layer 1 — Pre-commit (fast): Code-based evals only. Run on every code change. Must complete in < 60 seconds. Catches format and structural failures.

Layer 2 — Pre-deploy (medium): Code-based + LLM-as-judge on a representative sample. Run before any deployment. Should complete in < 10 minutes.

Layer 3 — Production monitoring (ongoing): LLM-as-judge on a sample of live outputs + human eval on flagged outputs. Run continuously or weekly.

Step 7 — Output

Produce:

• Eval suite design (one eval design per failure category)
• LLM-as-judge prompt(s) for subjective failure categories
• Three-layer eval structure with run frequency and completion time targets
• Minimum viable suite: which 3 evals to implement first to get 80% of the value?
• Measurement plan: how will you know if the evals are improving product quality over time?