Does the description disclose side effects, auth requirements, rate limits, or destructive behavior?

Annotations only give destructiveHint=true; the description adds crucial lifecycle context that the annotation cannot convey: the request starts pending, and cancellation is done via a separate update call with status 1. This is genuinely helpful behavioral detail. It doesn't cover permissions or idempotency, so not a 5.

Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

Is the description appropriately sized, front-loaded, and free of redundancy?

Three short sentences, front-loaded with the action, then state, then prerequisites and alternative. No filler; every clause has a concrete purpose (routing, lifecycle, endpoint).

Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

For a mutation tool with no output schema and full schema coverage, the description covers what an agent needs: the call's effect, initial state, cancel path, and type_id source. It omits raw HTTP/return details, but that's acceptable given the endpoint reference and schema.

Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

Schema coverage is 100%, so all six parameters are already documented in the schema, including defaults and formats. The description adds the type_id sourcing hint (via list_time_off_types), but otherwise restates rather than extends the schema. Baseline 3 applies since the schema does the heavy lifting.

Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

Does the description clearly state what the tool does and how it differs from similar tools?

States a specific verb+resource ('Create a time-off request') and adds scope ('for a user, default the calling user'). It distinguishes itself from sibling get/list/update tools by naming the exact creation action.

Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

Does the description explain when to use this tool, when not to, or what alternatives exist?

Explicitly routes to alternatives: use wheniwork_list_time_off_types to get type ids and wheniwork_update_time_off_request to cancel. States the initial state (pending) and the cancel condition (status 1), leaving no ambiguity about lifecycle.

Agents often have multiple tools that could apply. Explicit usage guidance like "use X instead of Y when Z" prevents misuse.