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

Annotations already declare readOnlyHint, idempotentHint, destructiveHint=false and openWorldHint=false, so the safety profile is covered. The description contributes the key non-annotation fact that results are scoped to the connected user's own documents and span two artifact categories (uploads and generated drafts). It does not mention result ordering or whether an empty list vs. pagination boundary behaves in any special way.

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 short sentences with zero filler; the resource scope comes first and the alternative-tool pointer follows. Every clause carries information an agent needs.

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 simple two-parameter read tool with rich annotations and full schema coverage, the description covers what is listed and how to follow up. The only soft gap is that it does not characterize the result set (ordering, whether drafts and uploads are distinguishable), though with no output schema that is a minor omission rather than a blocker.

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 limit and offset (including the 'use next_offset from the previous response' guidance) are already fully documented in the schema. The description adds no additional meaning about paging or sorting beyond that, so the baseline 3 applies.

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 ('List') and a precisely scoped resource: the connected user's uploaded source documents plus generated CV/cover-letter drafts. That scope immediately separates it from the other list_* siblings (list_experience, list_applications, list_saved_jobs), which cover different resource types.

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?

Explicitly routes the agent to get_document for reading content, which is the main ambiguity for a listing tool. It does not address when to prefer this over other list_* tools or whether drafts and source documents can be filtered apart, so it falls short of full when/when-not coverage.

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