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

Annotations already declare readOnly/idempotent/non-destructive, and the description adds genuine semantics on top: matching is word-based against name and description, results are capped at five and include the sentence saying when each applies, and an empty answer means no word match rather than an empty catalog. The auth prerequisite (Valet account connection) is also disclosed.

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 action and the when-to-call rule, and every sentence carries operational information. It is slightly dense and repeats the call instruction across two paragraphs, but no sentence is filler.

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 two-parameter search tool with no output schema, the description covers invocation timing, matching behavior, result count, result shape (best matches plus applicability sentence), empty-result meaning, and the account prerequisite. Nothing an agent needs to call or interpret it correctly is missing.

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% and already documents both parameters, including the org_name fallback behavior. The description reinforces what kind of words to pass ("words from the task") and that matching is lexical, but adds no format, tokenization, or ranking detail beyond the schema — the baseline 3 for fully covered schemas.

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+resource ("Search the organization's skills") and immediately clarifies what a skill is ("its playbooks for how it does things"). It also distinguishes itself from the two nearest siblings by name: get_skill for reading a match, list_skills for the full inventory.

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 invocation conditions: at the start of any task the organization may have a way of doing, with words from the task, and whenever the user names a skill the client lacks (with a concrete example, "use the duck skill"). It also names the follow-up action (get_skill) and the escape hatch when results are empty (list_skills).

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