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

Annotations only cover the safety profile (not read-only, not destructive, not idempotent, closed-world). The description adds substantial behavior beyond that: text-extraction of PDFs/Office/images, re-running deck analysis for multi-page pitch PDFs, and the context cost of base64 bytes. This is rich, non-obvious operational context.

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-loads the core action and the text/content selector first, then usage caveats. It is dense and slightly long, but nearly every sentence carries a distinct constraint (mutual exclusion, link delegation, allowed types, post-processing), so little is wasted.

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?

With no output schema, the description compensates by covering allowed file types, what happens after upload (text extraction, deck re-analysis), how to source the company/pitch slug, and the link-deck alternative. An agent has everything needed to call it correctly.

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 coverage is 100% so the baseline is 3, but the description adds a real constraint not enforced in the schema: exactly one of text or content must be supplied. It also clarifies the filename convention (.md/.txt) and the slug source for company. Genuine added meaning above the schema.

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 and resource ('Add a document to a company's or pitch's data room') and immediately anchors it to where uploads land in the web app. It also distinguishes itself from sibling update_company for the linked-deck case, so an agent can route without opening either 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 ('Give exactly one of text or content'), explicit when-not-to-use ('For a deck or document that lives at a link, don't upload it: set deck_url with update_company'), and names concrete document types it is meant for (memos, transcripts, user-handed files). Nothing is left to inference.

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