Prompt Engineering

Prompt Engineering

Purpose

Write prompts that produce the right output reliably, and diagnose the ones that do not. Prompt engineering is an empirical discipline: the model's actual behavior, measured, beats any theory about what should work.

When to Use

• Writing a prompt for a production feature.
• A prompt that works most of the time and fails unpredictably.
• Reducing token cost or latency without losing quality.
• Migrating a prompt between models.

Capabilities

• Instruction design: role, task, constraints, and output contract.
• Few-shot examples, and selecting the ones that teach the boundary.
• Reasoning elicitation for tasks that need it.
• Output formatting and structured extraction.
• Failure diagnosis and systematic iteration.

Inputs

• The task, and what a correct output looks like.
• Real failure cases from the current prompt.
• Constraints: latency, cost, and the model available.

Outputs

• A prompt with an explicit output contract.
• An evaluation set of inputs with expected outputs.
• A measured success rate, before and after.

Workflow

1. Define correct before writing the prompt — Twenty real inputs and their correct outputs. Without this, "improving" a prompt is a matter of opinion and you will optimize for the last example you looked at.
2. State the task, the constraints, and the output shape — Be specific about what to do, what not to do, and exactly what format the answer takes.
3. Add examples that teach the boundary — Two or three examples covering the ambiguous cases, not the obvious ones. An example of the hard case is worth ten of the easy one.
4. Elicit reasoning only where it helps — For multi-step reasoning, ask the model to work through it before answering. For classification and extraction, it adds latency and cost without improving accuracy.
5. Measure, change one thing, measure again — On the evaluation set. A change that improves one example and silently breaks three others is a regression that feels like progress.
6. Handle the failure mode — Decide what happens when the model returns something unparseable, refuses, or hallucinates a field. That path will be taken.

Best Practices

• Specificity beats politeness. "Return exactly one of: approve, reject, escalate" outperforms "please try to categorize this appropriately".
• Put the instructions before the data for short inputs, and after for long ones — models attend more reliably to the end of a long context.
• Negative instructions are weakly followed. "Do not include a preamble" works less well than "Begin your response with the JSON object."
• Structured output (a JSON schema, a tool call) is far more reliable than asking for JSON in prose and hoping. Use the API's native mechanism.
• Long, elaborate prompts accumulate contradictions. When a prompt exceeds a page, look for instructions that conflict — the model is following one of them.
• Prompt improvements do not transfer across models. Re-measure after any model change; a prompt tuned for one is not tuned for another.

Examples

A prompt with an explicit contract and a boundary example:

You classify customer support messages for routing.

Categories (choose exactly one):
- billing      — charges, invoices, refunds, payment methods
- technical    — errors, outages, broken functionality, integration problems
- account      — login, permissions, plan changes, cancellation
- other        — anything not clearly covered above

Rules:
- If a message spans two categories, choose the one the customer needs
  resolved first to be unblocked.
- If the message is too vague to classify with confidence, return "other"
  with confidence below 0.5. Do not guess.

Respond with JSON only, matching this schema:
{"category": "billing|technical|account|other", "confidence": 0.0-1.0, "reason": ""}

Examples:

Message: "I was charged twice for March and I can't log in to check."
{"category": "account", "confidence": 0.8, "reason": "The double charge matters, but they cannot access the account to act on it, so access is the blocker."}

Message: "hey"
{"category": "other", "confidence": 0.2, "reason": "No classifiable content."}

The first example is the one that earns its place: it teaches the tie-break rule in a way the prose alone does not.

Diagnosing a failing prompt systematically:

Symptom: the classifier returns "billing" for technical messages ~15% of the time.

Hypotheses, tested one at a time against the 40-case evaluation set:

H1: The category definitions overlap.
    Test: read them. "billing" says "payment methods"; several technical
    messages are about a broken payment *integration*.
    Result: CONFIRMED. Baseline 85% -> 94% after clarifying that integration
    failures are technical regardless of subject matter.

H2: Reasoning would help.
    Test: add "Think step by step before answering."
    Result: no accuracy change, +340ms latency, +180 tokens. REVERTED.

H3: More examples would help.
    Test: 6 examples instead of 2.
    Result: 94% -> 96%. Kept. Diminishing returns past 6 (tested 10: 96%).

Final: 96%, at lower cost than the baseline.

Notes

• The measurement set is the entire discipline. A prompt engineer without an evaluation set is guessing with extra confidence.
• "Think step by step" is not free and is not universally helpful. It reliably improves multi-step arithmetic and logic; it reliably does nothing for classification. Measure rather than assume.
• Prompt injection is a real vulnerability when user content enters a prompt. Never let user text be interpreted as instructions — delimit it clearly and treat the model's output as untrusted.

Source & license

This open-source skill is cataloged on AgentStack and links to its original source — we do not rehost the code.

• Author: nimadorostkar
• Source: nimadorostkar/Claude-Skills-collection
• License: MIT
• Homepage: https://github.com/nimadorostkar/Claude-Skills-collection

Install and usage instructions live in the source repository linked above.