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

Annotations indicate readOnlyHint=false, so mutating behavior is already implied. The description adds that it uploads to the connected account's profile, requires the jobs:apply permission, and accepts multiple file types. It could mention side effects like replacing previous resume or if it's idempotent, but the added context is valuable beyond annotations.

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?

Two sentences: the first states the action, scope, file types, and exact use case; the second states required permission. Every word earns its place, no fluff, and critical info is front-loaded.

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 destructive hint, the description covers the purpose, prerequisite permission, and use case. It doesn't explain return values, but an output schema exists. It could mention that it overwrites an existing resume, but given sibling delete_resume exists, that ambiguity is minor.

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 already provides 100% coverage with descriptions for all three parameters. The description adds that the file types can be PDF, Word, text, or image, which aligns with the MIME parameter and provides practical guidance. It doesn't deeply explain the content_base64 format beyond what schema says, but the schema is clear.

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?

Description clearly states the action (upload), the specific resource (connected account's profile resume file), and allowed file types. It distinguishes itself from siblings like get_resume and delete_resume, and mentions the specific use case (Apply resume gate before start_apply_with_ai).

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?

It explicitly says this is used by the Job Cards Apply resume gate before start_apply_with_ai, giving clear context of when it should be invoked. It also names a sibling (start_apply_with_ai) that likely follows this step, implying sequence. No explicit exclusions, but the context is strong enough.

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