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

With no annotations, the description carries the burden of behavioral disclosure. It adds useful context about the connection prerequisite and states that it returns the updated membership. However, it does not disclose potential side effects (e.g., overwriting the existing role) or any required permissions, leaving some behavioral ambiguity.

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 concise and front-loaded, with the purpose in the first sentence. Every sentence serves a function—purpose, prerequisite, return value—though the 'Cost = 8 tokens' line is arguably meta-information that could be omitted from a functional description.

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 role-change tool, the description covers the essential context: purpose, connection prerequisite, parameter usage, and return value. An output schema exists, so return details are not needed in the description. It could mention permissions or side effects, but overall it is sufficiently complete for the tool's complexity.

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 provides 100% coverage with detailed descriptions for all parameters, including the clerk_instance_id behavior. The description slightly reinforces the clerk_instance_id usage but does not add substantial meaning beyond what the schema already conveys. Baseline of 3 is appropriate.

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 'Change the role of a Clerk organization member', which is a specific verb+resource statement that clearly distinguishes this tool from siblings like create_organization_membership, delete_organization_membership, and update_organization_membership_metadata. It accurately conveys the tool's core purpose.

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 a clear prerequisite—'Call clerk.get_connected_accounts first'—and clarifies how to target a specific connection via clerk_instance_id. However, it does not explicitly mention when to use this tool versus alternatives (e.g., creating or deleting memberships), so it lacks explicit exclusion guidance.

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