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

Annotations already declare destructiveHint=true and readOnlyHint=false, so the mutation is known. The description adds valuable context: soft-delete behavior, reset of signing history, optional Monday asset removal, and the confirm_token retry mechanism. It doesn't fully explain consequences of resetting signing history, but it covers the key behavioral traits.

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 sentences, front-loaded with the action, then the mechanism, then the prerequisite. Every sentence earns its place with no fluff.

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 destructive mutation with no output schema, the description covers the critical context: what happens, what to do before calling, and the confirmation requirement. It could mention the CONFIRMATION_REQUIRED response flow more explicitly, but the confirm_token schema description covers that.

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 20%, so the description must compensate. It explains file_id and asset_id semantics (file to delete, optional Monday asset), and mentions confirm_token's purpose indirectly via the confirmation warning. However, envelope_id and item_id are not explained in the description, leaving some 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?

The description states a specific verb ('Remove'), a resource ('document from a workflow/envelope'), and the underlying API call (DELETE /api/v3/files/:fileId). It also distinguishes itself from siblings by mentioning the optional Monday asset removal and the prerequisite list tool.

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 instructs to confirm with the user before calling, warns that it mutates the envelope, and directs the agent to use getsign_list_envelope_documents first to discover file_id/asset_id. This is clear when-to-use and when-not-to-use guidance.

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