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

Annotations already declare readOnly, idempotent, non-destructive, and closed-world, so safety is covered. The description adds genuinely new behavioral context with no output schema present: the response contains a slug and the question each guide answers, which tells the agent exactly what payload shape to expect before fetching details.

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?

Two tight sentences: the first establishes what the resource is, the second states the return shape. Nothing is repeated from the name or annotations, and the most decision-relevant fact (what you get back) is placed second but unhurried.

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 zero-param, read-only listing tool with full annotation coverage, the description supplies the one missing piece — return content — since there is no output schema. It lacks only volume/pagination expectations (whether all guides come back in one call), a minor gap for a small curated catalog.

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 the baseline is 4; there is nothing for the description to clarify and it correctly does not waste text on inputs. The schema is an empty object with additionalProperties=false, consistent with the description's parameterless framing.

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 ('list_guides' → 'short practical guides the firm has written') and scopes the content to difficult technology decisions. It implicitly distinguishes itself from the sibling get_guide by saying it returns only each guide's slug and question, i.e. an index rather than full content, though it never 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 implied rather than stated: returning slugs and questions signals a discovery step before get_guide, but the description never says 'use this first, then call get_guide for the full guide' or set any exclusion. An agent must infer the workflow from the sibling names.

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