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

With no annotations, the description carries the full burden and discloses return fields ('membership id, organization_id, role, and timestamps') and cost. It also notes the connection prerequisite. Listing is inherently read-only, and no side effects are mentioned, but the description 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 sentences, front-loaded with the core purpose, and includes only necessary details: prerequisite, return fields, and cost. No filler.

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 read-only list tool with a complete schema and output schema, the description covers the main purpose, prerequisite, return contents, and cost. It doesn't need to explain pagination since limit/offset are self-descriptive in the schema.

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 input schema already documents all 4 parameters with descriptions (100% coverage), so the baseline is 3. The description adds value by explaining clerk_instance_id's relationship to get_connected_accounts and the fallback to default account, which supplements 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?

The description clearly states 'List all organizations a specific Clerk user belongs to' with a specific verb and resource. It distinguishes itself from sibling tools like list_organizations and list_organization_memberships by explicitly scoping to a user's memberships.

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?

It provides an explicit prerequisite: 'Call clerk.get_connected_accounts first' and explains how to target a specific connection via clerk_instance_id. This gives clear context for use, though it doesn't explicitly contrast with alternatives like list_organization_memberships.

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