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

Beyond the destructiveHint annotation, the description discloses concrete behavioral traits: it clears the Agree state, explicitly does not run plays, has a synchronous 'operator sits through the list' execution model, and explains the write-tier approval flow. This is exactly the kind of contextual behavior an agent needs that annotations alone do not provide.

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 core purpose is front-loaded in the first sentence, and every added line carries a distinct fact: side effect, non-execution, execution model, routing condition, and approval protocol. The approval block is dense and jargon-heavy ('the card is the yes'), but it is relevant operational guidance 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?

For a destructive batch tool with no output schema, the description covers scope, side effects, non-execution, routing, and authorization workflow, and the schema covers both parameters. Missing pieces are a clear statement of return/confirmation behavior and explicit definitions of domain-specific terms like 'engine-photocopy Play.'

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 description coverage is 100%, and both parameters are already well documented in the input schema, including the companyId membership requirement and limit defaults/max. The description adds no parameter-level meaning beyond the schema, so the baseline score 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?

The description states a specific verb and resource: re-draft every assigned engine-photocopy Play in the company into an English operator contract, and it adds key non-actions ('Clears Agree on each', 'Does not run'). It is not a tautology and is distinguishable from run_playbook and agree_playbook, though it does not explicitly name close siblings like redraft_playbook_contract or define the jargon 'engine-photocopy Play'.

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 'Routing' line gives an explicit applicability condition: clean engine Play slugs across the company should route to this tool. It also gives an invocation rule about acting on the first clear approval and not re-asking, which is practical guidance. It does not spell out when to prefer an alternative like redraft_playbook_contract for a single play.

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