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

Annotations already declare readOnlyHint, idempotentHint, destructiveHint=false and openWorldHint=false, so safety is covered. The description adds useful context about output format (Markdown) and the breadth of returned content, but says nothing about guide size, truncation, or failure behavior when a path does not resolve.

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?

Three tight sentences, front-loaded with the return value and its format, then the audience, then the input. The long list of included sections is justified because it tells the agent the payload is large, though it could be trimmed slightly.

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 single-parameter, read-only retrieval tool with an output schema and rich annotations, the description covers what is returned, in what format, when to prefer it, and how to address the guide. Nothing an agent needs in order to call 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 description coverage is 100% and the single 'guide' parameter is fully documented, including the same '/answers/tailor-cv-to-job-description' example the description repeats. The description adds no new meaning beyond path-versus-URL acceptance, so this lands at the 3 baseline.

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: 'Returns the full text of one OffLadder career guide as Markdown', then enumerates exactly what is included (answer, takeaways, sections, examples, templates, FAQs, sources). It distinguishes itself from a short-answer variant, though it never names the sibling tools (find_career_guide, browse_career_guides) it should be chosen over.

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?

'Suits someone who wants the step-by-step version of a guide rather than its short answer' gives a clear selection criterion against the shorter alternative. It does not explicitly say when to use this instead of browse_career_guides or find_career_guide, but the guidance is unambiguous for the primary decision.

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