Page 6 of 8~96 min topic

Context window suitcase

Evaluate with evidence

Measure context window with denominators, slices, and gates chosen before seeing results on the contract-review assistant.

~12 min this pageEvaluation

1Learn the idea

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Metrics

Track for context window: overflow rate, obligation-coverage on long contracts, p95 tokens in, cost per review. Report fractions like 36/40, not vague quality adjectives. Segment by language, plan tier, document length, or other slices that matter for the contract-review assistant.

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Protocol

Freeze inputs and neighboring versions while evaluating context window. Change one control. Pair results case by case on the contract-review assistant. Define hard gates (severe errors, privacy, latency) before the bake-off. Use deterministic checks where possible; humans for nuance; model judges only with calibration against gold.

Numeric reminder for context window: A 32k window with 8k system+tools, 12k retrieved exhibits, 6k history leaves ~6k for the draft—and less if tokenization is heavier than word count suggests.

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Make it operational

Resist adding a twelfth metric before the first three for context window on the contract-review assistant have owners. This workload improves faster when a small scorecard is trusted than when a warehouse of unused plots exists.

Also pin one numeric memory from this context window chapter: A 32k window with 8k system+tools, 12k retrieved exhibits, 6k history leaves ~6k for the draft—and less if tokenization is heavier than word count suggests. That number is not decoration; it is a template for how claims about context window on the contract-review assistant should look in design docs. Scoped specifically to context window / contract-review assistant / evaluation.

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Common mix-ups

People confuse context window with neighboring buzzwords when debugging the contract-review assistant. Before changing prompts, ask whether the broken stage was evidence gathering, the context window judgment itself, validation, or the product action. Fixing the wrong stage creates folklore (“we tried context window and it failed”) that blocks the next team on the contract-review assistant. Scoped specifically to context window / contract-review assistant / evaluation.

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Rehearsal (context-window/evaluation)

Write a five-line artifact for this page: goal, inputs, check, owner, stop rule. Invent one fluent failure that the check would catch. Keep details specific to context window rather than generic AI advice.

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Rehearsal (context-window/evaluation)

Write a five-line artifact for this page: goal, inputs, check, owner, stop rule. Invent one fluent failure that the check would catch. Keep details specific to context window rather than generic AI advice.

Read

Rehearsal (context-window/evaluation)

Write a five-line artifact for this page: goal, inputs, check, owner, stop rule. Invent one fluent failure that the check would catch. Keep details specific to context window rather than generic AI advice.

Read

Rehearsal (context-window/evaluation)

Write a five-line artifact for this page: goal, inputs, check, owner, stop rule. Invent one fluent failure that the check would catch. Keep details specific to context window rather than generic AI advice.

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Why this matters

A demo of the contract-review assistant looks great on three hand-picked examples of context window. What does that demo refuse to tell you?

In the wild

See how this idea shows up as a product and a company — then come back to the lesson. Skills transfer across vendors.

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