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

Adds substantial context beyond the annotations: 'Fixed rules, no model' explains why the operation is deterministic and idempotent, 'Contact details are removed before the check; the resume and the posting are not stored' discloses data handling, and the sign-in plus Interview Coach Pass requirement is an auth constraint the annotations do not carry. It also describes how output items are constructed and traced back to posting requirements and resume lines.

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?

Purpose and output shape are front-loaded, then constraints (determinism, privacy, auth) follow in a logical order with no repeated sentences. Some phrasing is dense and slightly awkward ('Fixed rules, no model', 'the check'), costing a point on clarity.

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?

With no output schema, the description carries the burden of describing the return value, and it does so at a useful level of detail (three horizons, requirement traceability). Privacy, auth, and determinism are covered; what's missing is any sense of output size/format or failure behavior, a minor gap for a read-only generator.

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 the baseline is 3, but the description earns more by explaining how the two required inputs are used — the plan is built from the posting's requirements and each item is paired with a matching resume line. The optional 'role' parameter is not addressed in the description, keeping it short of a 5.

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 artifact ('Drafts a 30-60-90 day plan skeleton') scoped to one job posting, and enumerates the three horizons the output covers. This artifact is clearly distinct from the sibling set (prepare_interview_plan, match_resume_to_job, review_resume), so an agent can route without opening a 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?

Usage is implied by the required inputs (resume + full posting) and the stated sign-in/pass prerequisite, which tells the agent when the call will succeed. But it never names an alternative or exclusion — e.g. when to use prepare_interview_plan or match_resume_to_job instead — leaving the agent to infer selection.

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