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

Annotations already declare readOnlyHint, idempotentHint, destructiveHint=false and openWorldHint=false, so the safety profile is covered. The description adds the return shape (each hit with id, title and surrounding text), which is genuinely useful, but says nothing about pagination, result limits, or match behavior.

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?

A single front-loaded sentence that defines the resource and the return shape with essentially no waste. The parenthetical aside ('the facts about the company the tommos read') is useful context, though the phrasing is stylistically awkward.

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 one-parameter, non-destructive search with no output schema and full annotation coverage, the description is adequate: it explains what is searched and what a hit contains. Only result-count/pagination behavior is left unaddressed.

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 0% for the single 'query' parameter, so the description must compensate. 'By words' does convey that this is a keyword/text search rather than an exact-ID lookup, adding some meaning beyond the bare string type, but it omits matching semantics (whole word, phrase, multi-word AND/OR).

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 (search) and resource (the Playbook's pages), and clarifies what the Playbook is ('the facts about the company the tommos read'). It also previews the hit shape (id, title, surrounding text), which distinguishes it from read_a_playbook_page, though it never explicitly names that sibling.

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?

Usage is only implied: 'search...by words' suggests keyword lookup as opposed to reading a single page via read_a_playbook_page. There is no explicit when-to-use/when-not statement or named alternative.

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