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

Annotations provide readOnlyHint=false, destructiveHint=true, and openWorldHint=true, which already signal a mutating, potentially destructive operation. The description adds critical context beyond these: that the old secret remains valid for a grace window (mitigating destructive risk) and that the new secret is returned only once. It also gives the zero-downtime behavior. This is strong transparency that enhances understanding of the operation's side effects.

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 a single, compact sentence that front-loads the core action and immediately states the key benefit (zero downtime) and the critical consequence (old secret stays valid). Every phrase adds value, with no wasted words. Perfect conciseness for a one-line tool 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?

Given the tool's moderate complexity (two parameters, no output schema), the description covers the essential aspects: purpose, key behaviors (zero downtime, grace window, one-time return), and param hints. The main gap is not mentioning that the returned secret is sensitive and should be handled securely, but that is inferable. It is complete enough for an agent to call correctly.

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 50%: 'id' is described as 'Company id', but 'webhook_id' has no description. The description does not explain what these parameters are beyond the schema; however, the names are self-explanatory. It adds minimal value (e.g., confirming 'id' is a company id), but given partial coverage, a 3 is appropriate—not lower because the schema already conveys intent.

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 a specific action ('rotate a company webhook signing secret') with a concrete resource and a notable property (zero downtime). It distinguishes itself from the sibling hires_rotate_job_webhook_secret by specifying 'company webhook' vs 'job webhook', so an agent can tell them apart. It's not a 5 because it doesn't explicitly name the sibling or the condition for choosing between them, but the purpose is unambiguous.

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 implies when to use this tool (when a company webhook secret needs rotation) and highlights the zero-downtime benefit. However, it does not explicitly state when not to use it (e.g., for job webhooks) or mention alternatives like the sibling hires_rotate_job_webhook_secret. The guidance is adequate but not explicit.

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