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

Annotations already declare destructiveHint=true and idempotentHint=false; the description goes beyond them by spelling out exactly what is destroyed — the current main resume is replaced — and what survives (the other saved resumes, up to 5 per account). It does not cover failure modes or file-size limits, but the destructive blast radius is clearly communicated.

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 the replacement semantics, then the parameter directive. Nothing is redundant with the schema or annotations.

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?

An output schema exists and annotations carry the safety profile, so the description only needs to add the semantics those can't express — replacement of the main resume, retention of the other four — which it does. Minor omissions are what happens on unsupported MIME types or oversized files.

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, and the description adds real value by disambiguating the two input modes: it directs the caller to pass the chat attachment as resume_file rather than content_base64. It does not explain when the base64/mime/filename path applies, which is the remaining gap.

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 (save the attached resume as the main resume on the Worklittle profile) plus the purpose (so it can be used to apply). It is clearly distinguishable from siblings like get_my_resume, delete_my_resume and apply_for_job without opening any 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?

The trigger condition is explicit: use this when the user has attached a resume in the chat and it should become the main resume. It does not name alternatives (e.g. use get_my_resume to inspect, delete_my_resume to remove), so there is no explicit when-not, but the usage context is unambiguous.

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