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

Annotations already declare readOnly, idempotent, non-destructive, and closed-world, so the safety profile is fully covered. The description adds the tool's identity as a coaching assistant but nothing beyond that — no note on latency, session continuity, or how modes differ behaviorally.

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?

A single well-formed sentence with zero filler, front-loading the actor and the action. Nothing could be trimmed without losing meaning.

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 tool with rich enum parameters, no output schema, and full annotation coverage, the description is thin but the structured fields carry the load. It does not clarify what Otto returns or how 'plan'/'coach' modes differ in practice, leaving some agent uncertainty.

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 all five parameters (including the mode/topic enums) are already documented in the schema. The description's mention of 'search, an application or a company' loosely echoes company_slug/application_id but adds no syntax or format detail beyond what the schema provides. Baseline 3 is appropriate.

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 (Ask) and resource (Otto, a job search coach), and scopes the subject matter to the member's search, an application, or a company. It is clearly distinguishable from the CRUD-style siblings, though it relies on the branded name 'Otto' which the description helpfully glosses.

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?

Implies when to use it by naming the topical domains (search, application, company), but gives no explicit when-not guidance or pointers to alternatives. There is no sibling that overlaps, so the omission is less costly, but the agent still gets no signal on what Otto is not for.

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