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

Annotations already declare readOnlyHint, idempotentHint, destructiveHint=false and openWorldHint=false, so 'Read-only and free' is largely redundant. What the description genuinely adds is policy-level behavior an agent must obey when acting on the guide: relay validated venues only, invent no details, respect legal drinking age.

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 sentence with a colon-led list covering purpose, contents and constraints, all front-loaded with zero filler. The only weak clause is 'Read-only and free', which restates annotations, but it costs almost nothing.

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 parameters, no output schema and rich annotations, the definition covers what the guide contains and the rules it imposes, which is enough to call it correctly. It does not indicate the guide's shape or length, but that is a minor gap for a static reference tool.

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 tool takes zero parameters, so there is nothing for the description to disambiguate and the baseline of 4 applies. The empty schema with additionalProperties=false is self-explanatory.

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 states a specific resource — a usage guide for the night-out planner — and enumerates its contents (largest places, supported vibes, relaying rules), so an agent knows this is reference material rather than a planning action. It never names the sibling drinkedin_plan_night_out, so the differentiation from the action tool is only implied by the word 'How to use'.

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?

Framing it as 'How to use the night-out planner' plus 'the rules to follow when relaying a plan' strongly implies this should be read before or alongside planning, but there is no explicit 'call this first' or 'use X instead' statement referencing drinkedin_plan_night_out. Usage is inferable but not spelled out.

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