clio_upload_document

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

With no annotations, the description carries the full burden. It adds a meaningful behavioral detail ('Handles Clio's multi-step storage upload atomically'), which implies safety and internal complexity. However, it does not disclose permissions, return values, error conditions, or what happens if both matter_id and parent_folder_id are provided.

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?

The description is two sentences long, with no wasted words. The first sentence states the primary purpose, and the second adds an important execution detail. It is front-loaded and efficient.

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?

The tool has 5 parameters, no output schema, and no annotations. The description does not explain whether matter_id or parent_folder_id is required, how content_type is determined, or what the function returns. It is terse and leaves significant ambiguities for a multi-step upload operation.

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 only 40%, so the description must compensate. The phrase 'under a matter or folder' gives semantic meaning to matter_id and parent_folder_id, which lack schema descriptions. However, content_type is entirely unexplained, and the relationship between matter_id and parent_folder_id is ambiguous. This is partial compensation.

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?

The description uses a specific verb ('Upload') and resource ('local file as a new document'), and clarifies placement ('under a matter or folder'). This clearly distinguishes it from siblings like clio_download_document, clio_get_document, clio_update_document, and clio_delete_document.

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 description clearly indicates when to use the tool—when uploading a new local file as a document under a matter or folder. It does not explicitly mention exclusions or alternatives, but no direct upload alternative exists among the siblings, so the context is sufficient. It could improve by noting that it is not for updating existing documents.

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