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

No annotations are provided, so the description carries the burden. It discloses the return shape ('Returns role summaries with nested permissions and total_count') and cost ('Cost = 5 tokens'), and clarifies default connection behavior. While it does not explicitly state read-only nature, the verb 'List' implies it, and the response summary adds useful behavioral context.

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?

The description is four short, front-loaded sentences: purpose, prerequisite/usage, return summary, and cost. Every sentence earns its place with no redundancy or filler. The structure is scannable and effective.

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?

Given the tool's moderate complexity (5 optional params, output schema available), the description covers the prerequisite, connection targeting, return shape, and cost. It might have mentioned the sibling get_organization_role for single-role lookups, but the list-vs-get distinction is obvious. Overall, it is sufficiently complete.

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?

With 100% schema coverage, the baseline is 3. The description adds meaningful semantic value for clerk_instance_id by explaining how to target a specific connection versus the default, which goes beyond the schema's dry description. It does not need to elaborate on the other parameters since the schema already documents them thoroughly.

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 opens with 'List organization roles in a connected Clerk application,' which is a specific verb+resource statement that clearly identifies the tool's function. It inherently distinguishes itself from sibling tools like list_organizations and list_organization_permissions by naming the exact resource (organization roles) and scope (connected Clerk application).

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?

The description provides explicit usage guidance: 'Call clerk.get_connected_accounts first' establishes a prerequisite, and 'Pass clerk_instance_id to target a specific connection, or omit it to use the default account' clarifies when to use the instance parameter. It does not mention alternatives or when not to use the tool, so it falls short of a 5.

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