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

Annotations already declare readOnlyHint=true, destructiveHint=false, and openWorldHint=true, so the safety profile is covered. The description adds genuinely useful behavior beyond that: fixed page size of 30 and name-ordering of results, which an agent needs to plan paging. It does not state what happens at the end of the collection, keeping it short of a 5.

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?

One compact sentence that front-loads the action and resource, then supplies the two most operationally relevant facts (page size, sort order) and the endpoint. Nothing is wasted or repeated.

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 simple, read-only, two-optional-parameter listing tool with full schema coverage and populated annotations, this covers what an agent needs to invoke it. The only real gap is termination/paging guidance ('stop when fewer than 30 returned'), which would make it fully self-sufficient.

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%, so both offset and include_custom_fields are already well documented, establishing a baseline of 3. The description's page-size and sort-order context indirectly informs how offset behaves, but it adds no syntax or formatting detail beyond the schema.

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 ('List companies') and clarifies the resource as 'customer organisations', which disambiguates it from contact and ticket listings. It does not explicitly contrast itself with desk365_get_company, but the list-vs-get verb separation makes the distinction reasonably clear.

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 by the verb 'List' and the endpoint note, and the '30 per call, sorted by name' detail hints that pagination is expected. However, there is no explicit when-to-use guidance, no mention of desk365_get_company as the single-record alternative, and no advice on how to page through results.

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