A useful evaluation connects a realistic task, a clear success condition and an observable failure.
Start with the actual job
Write down the tasks the product is expected to perform and the mistakes that would make the result unusable. Include normal cases, difficult cases and situations where the correct response is to stop or ask for clarification. A generic benchmark may offer context, but it cannot replace evidence about the customer workflow. The test should reflect what the product promises to do.
Separate dimensions of quality
An answer can be fluent but unsupported, correct but too late, or complete but produced through an unacceptable action. Evaluate those dimensions separately. For a hypothetical invoice assistant, extracting the right amount and sending it to the right account are different checks. A single average score can conceal a serious failure in one part of the workflow.
A practical evaluation system
Task
Represent the customer’s real job.
Criteria
Define correctness, safety and usability.
Compare
Run a stable, versioned case set.
Release
Connect failures to a shipping decision.
Keep a stable comparison set
Retain a versioned set of cases so changes can be compared with the same baseline. Add real failure cases after investigating them, while keeping a separate holdout for broader assessment. Record the model, prompts, tools and relevant settings used in a run. Without that context, the team may be unable to explain whether a change improved the product or simply changed the test conditions.
Use evaluation to make release decisions
Define which failures block release and which can be handled through a visible limitation or review step. Inspect examples behind score changes instead of trusting a dashboard alone. Evaluation is useful when it changes a decision: which version ships, where human review is required or which task should remain unsupported. The objective is a dependable product boundary, not a number that looks better in a launch announcement.
Sources
- Anthropic — source and reference material ↗ Anthropic · Primary source
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