doc_outline

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

Annotations are absent, so the description carries the full burden. It does disclose the performance cost of the summarize flag ('runs the summarizer once per chunk... slow on large documents'), which is a behavioral trait. However, it does not state whether the operation is read-only or has side effects (e.g., caching is mentioned only in the schema, not here), nor does it address error behavior for invalid doc_id. For a no-annotation tool, this is a moderate disclosure, hence a 3.

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 extremely concise: two sentences total. The first sentence front-loads the core purpose and output contents, while the second gives workflow context and a cost warning. Every clause earns its place, with no repetition or filler. Structure is ideal for quick agent consumption.

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?

Given that there is no output schema and no annotations, the description must explain behavior and expected outputs. It covers the main purpose, when to call it, and the summarization cost. It explicitly lists the output components (chunk index, heading, size) and hints at the workflow. It does not describe the exact return format (e.g., list vs. map) or error cases, but for a simple outline tool this is largely sufficient. A 4 reflects that it is nearly complete without going overboard.

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?

The schema already documents all three parameters with descriptions (100% coverage), so the baseline is 3. The description adds a performance note about the summarize parameter, which goes beyond the schema's simple 'generate and cache a short summary'. However, it does not add any meaning to doc_id or max_chunks beyond what the schema provides. The added value is limited but present, so a 3 is appropriate.

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 opens with a specific verb and resource: 'Show the structure of an ingested document' and enumerates exactly what the result contains ('every chunk with its index, heading and size'). It clearly distinguishes its role from siblings like doc_summarize (whole-document summary) and doc_search by framing it as a structural overview. The purpose is unambiguous and fully stated in the first sentence.

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 gives an explicit when-to-use instruction: 'Call this right after doc_ingest to decide what is worth reading.' This tells the agent the exact workflow position and decision purpose. It also implies not to use it for other tasks and provides a trade-off for the summarize option. This is direct, actionable guidance that prevents misuse.

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