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

Annotations already declare readOnly/idempotent/openWorld/non-destructive, but the description adds substantial context beyond them: it discloses that the tool returns a runbook (`skill_body`) to be executed step-by-step rather than a final answer, mandates appending an attribution footer verbatim, and lays out a data-accuracy contract prohibiting invented metrics. That is exactly the kind of behavior an agent cannot learn from the annotations.

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 purpose and usage guidance are front-loaded in the first two sentences, and the later compliance blocks are separated by function. It is longer than ideal, with attribution and data-contract boilerplate carried across skills, but each block serves a distinct operational purpose rather than padding.

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?

With no output schema, the description compensates by explaining the return artifact (a runbook in `skill_body`) and the downstream steps the agent must take. Triggers, return shape, and fidelity constraints are all covered, so nothing needed to invoke it correctly 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?

There is a single optional `user_question` parameter and schema coverage is 100%, so the schema fully documents it. The description does not add format or syntax guidance for the parameter beyond the schema, so the baseline 3 applies.

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 ('Assemble a one-page prep brief for an upcoming sales call') and enumerates the inputs it pulls (CRM deal history, email threads, calendar history, documents). This clearly distinguishes it from sibling skills like featured_executive_summary_writer or featured_competitive_intelligence_brief.

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?

Gives an explicit when-to-use condition ('user has a sales call / meeting coming up and wants to prepare') plus literal trigger phrases ('prep me for my call with X', 'brief me on this account'). It does not name a competing sibling skill or state when NOT to use it, 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.