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

Annotations already disclose that this is a non-readonly, open-world, non-idempotent, destructive operation. The description adds valuable behavioral context: it starts conversations, uses a shared group or a default, refuses self-messages, may be limited by level, sends under the user's name, and cannot be deleted.

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 front-loaded and appropriately sized, but the first sentence and the beginning of the second sentence overlap substantially. The redundancy is minor and does not obscure the key behavior.

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 send-message mutation with annotations and no output schema, the description covers the important caller-facing behavior: conversation creation, group selection, self-message refusal, level restrictions, attribution, and non-deletability. Nothing essential for correct invocation 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 coverage is 100%, so the schema already documents member_id, body, and group. The description adds meaning beyond the schema by explaining that the group must be shared and that Skool will fall back to the first accepted group.

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 gives a specific verb and resource: send a direct message in Skool Chat to one member. It also states that it starts a conversation if needed, which distinguishes it from read-only siblings such as get_conversation and list_conversations.

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 clearly explains the use case and several constraints: a group must be shared, self-messaging is refused, and group chat may be level-limited. It does not explicitly name alternatives among siblings, but the context is strong enough to guide selection.

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