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

Annotations already cover readOnly, idempotent, non-destructive and closed-world, so the bar is lower; the description adds genuine value by disclosing the return contents (the tailor's questions in order, the occasions he dresses for, the full kit per impression) since no output schema exists. It does not clarify whether starting a fitting creates resumable session state, which is relevant given idempotentHint=true.

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 identity, then usage triggers, then return content. The example list is long but each item maps to a real enum value, so it earns its space; the final sentence about plan_outfit could be folded in more tightly.

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 usefully explains what comes back and how it connects to the sibling tool, and the occasion examples align with the enum. The only gap is statefulness/session behavior, which an agent calling a 'start' tool would want to know.

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 the single optional 'room' parameter is documented with a five-value enum in the schema. The description's occasion examples mirror those enum values but add no format or semantics beyond what the schema already provides, so the 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 specific verb and resource (start a guided fitting) plus what the tool actually is (an independent menswear concierge), and explicitly names quartermaster_plan_outfit as the consumer of the output, so the agent can separate it from the other quartermaster siblings.

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?

Gives clear triggering conditions with concrete user phrasings ('what should I wear to my friend's wedding', 'I have nothing to wear') and states the downstream step (answers feed quartermaster_plan_outfit). It lacks any when-not-to-use guidance, e.g. that a single-piece question should route to quartermaster_check_piece instead.

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