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

Annotations only declare destructiveHint=true, so most behavioral burden falls on the description, which usefully discloses that the request "starts pending" rather than being auto-approved and points to the cancel mechanism. It adds real lifecycle context beyond the annotations, though it does not cover approval flow, notifications, or overlapping-request handling.

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 tight sentences, front-loaded with the action and default, then lifecycle, then the type-id source, then the raw endpoint. No filler; every clause carries information.

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 six-parameter creation tool with no output schema and annotations covering only destructiveness, the description supplies the missing lifecycle and prerequisite-routing context. It is essentially complete for correct invocation, with only edge-case behavior (overlaps, approval side effects) left unstated.

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 description coverage is 100%, so the parameters are already documented, giving a baseline of 3. The description only restates the calling-user default and points to the sibling tool for type_id values, adding minimal meaning beyond the schema.

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 and resource ("Create a time-off request") plus the default target user, which cleanly separates it from wheniwork_get_time_off_request, wheniwork_list_time_off_requests, and wheniwork_update_time_off_request. An agent can identify the operation without opening the schema.

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?

Names the prerequisite sibling (wheniwork_list_time_off_types for type ids) and the alternative path for undoing the action (wheniwork_update_time_off_request with status 1). It lacks an explicit "do not use when..." framing, but the routing context is strong and actionable.

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