get_document_outline

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

No annotations are supplied, so the description carries the burden and does disclose one non-obvious behavioral trait: returned indices line up with edit_document's '#N' addressing, which is not inferable from the schema. It is silent on failure behavior for unsupported formats or size limits, and the return-value section partly duplicates the existing output schema.

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?

Front-loaded with the core action, then usage, then return shape in a scannable list; no filler sentences. The 'Returns a dictionary with' block is somewhat redundant against the declared output schema, costing a point on tightness.

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 3-parameter read tool with full schema coverage and an output schema, the description covers purpose, navigation use case, and cross-tool index semantics. Remaining gaps are minor: no note on unsupported formats or how errors surface.

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 doc, max_level, and format_hint are already well documented in the input schema. The description adds no parameter-level meaning (e.g., when to set format_hint or how max_level affects indices), so 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 concrete verb and resource: 'Return the heading structure (table of contents) of a document.' The parenthetical clarifies the concept and the follow-up sentence scopes it to navigation of large documents, which separates it from read_document_as_markdown (full content) and search_documents (query match) without needing the 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?

Explicit when-to-use: 'navigate a large document before extracting specific sections,' and it points at a downstream consumer (edit_document's '#N' notation). It stops short of naming an alternative sibling or a case where this tool is the wrong choice, so it is clear context without explicit exclusions.

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