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

Annotations already cover the safety profile (readOnly, idempotent, non-destructive), and the description adds genuinely new behavioral context: the three mutually exclusive path outcomes, the 'dead zone' rule the tool adjudicates itself (with the explicit instruction to report its verdict rather than infer one), the four 2027 checks, and the per-month proof artifact. It also discloses that the context parameter is recorded as intent and never changes the answer.

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?

Front-loaded with the triggering user questions and then the output promise, which is the right order for an agent deciding whether to call. The embedded list of quoted user phrasings and the four check names make it dense, but each sentence carries routing or invocation information rather than filler.

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 9-parameter, zero-required, branched tool with an output schema, the description supplies everything an agent needs to call it correctly: trigger conditions, the empty-call warm-up, one-question-at-a-time collection, and the two-call completion pattern. Return-value details can be deferred to the output schema.

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 baseline would be 3, but the description adds real meaning: it explains that people_led and hands_on_hours_per_week jointly drive the dead-zone determination, that the yes/not_sure/no questions map to the four 2027 checks, and that the tool must be called once empty and once full. It does not explain the enum-style string values beyond what the schema already lists.

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: it picks one of three leadership career paths and returns a month-by-month 6-month plan with proof artifacts. It is instantly distinguishable from every sibling (launch readiness, leadership ratio, partnership case), none of which touch career planning.

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 opening lists the exact user questions that should trigger this tool ('what is my next role?', 'should I become a director or go back to IC?'), and it spells out the two-phase invocation: call with no arguments for the 7 questions, ask them one at a time, then call again with all answers. No explicit when-not-to-use or sibling alternatives are given, but the siblings are unrelated, so the gap is minor.

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