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

With no annotations provided, the description carries the full burden, and it does well: it discloses that the tool auto-scans the project, ranks fixes by impact, sequences quick wins first, tells whether the deadline is achievable, and requires a Pro plan. The only notable gap is that it does not describe the output format or clarify that optional parameters exist despite saying 'no arguments.'

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?

Three sentences, all informative and front-loaded. The first sentence states the core deliverable, the second explains the tool's behavior, and the third provides access requirements and a fallback option. There is no fluff or redundant restating of the tool name.

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 tool with no output schema and many siblings, the description provides enough context: the roadmap is week-by-week, prioritized, deadline-aware, and requires Pro. It also includes an alternative for free users. The main gap is that it does not describe the exact return structure or how optional parameters affect the generated roadmap, though these are partly covered by the 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 schema already documents all three parameters (deadline, project_path, risk_category). The description adds limited semantic value by saying 'no arguments' and noting auto-scan behavior, which helps explain the defaults, but it does not elaborate on the optional parameters. This matches the baseline 3 for a fully schema-documented parameter set.

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 opens with a specific deliverable: 'Get a prioritized, week-by-week plan to close every compliance gap before Aug 2027.' This clearly identifies the tool as a roadmap generator and distinguishes it from sibling tools like check_compliance and generate_report. The mention of ranking, sequencing, and deadline feasibility further sharpens its unique purpose.

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 gives clear context: it is a Pro-plan tool and points users to check_compliance() as a free alternative. It also implies this is the tool to use when a full prioritized plan is needed rather than a simple gap summary. It does not explicitly discuss other siblings like combined_compliance_report, but the stated alternative is a useful decision point.

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