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

The description discloses key behaviors beyond the annotations: the difference between retrieval (`generate=false`) and generation (`generate=true`), the ~15-30 second delay for generation, and the prerequisite of a completed screen. It also explains the `memo_type` semantics. It adds valuable context without contradicting 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 description is concise and well-structured. It opens with a clear one-liner, then uses conditional statements for the dual behavior, and lists parameters with explanations. Every sentence adds value, and it avoids redundancy with the schema.

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 dual behavior and a prerequisite, the description covers the essentials: what it does, when to use it, and parameter details. However, it omits edge cases such as what happens if a memo already exists when generating, or if no memo is found when retrieving. The presence of an output schema reduces the need to describe return values, but slightly more behavioral edge-case info would increase completeness.

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?

The description provides thorough explanations for all three parameters beyond the schema: `deal_id` source, `generate` toggles behavior, and `memo_type` meanings. Since schema description coverage is 0%, this fully compensates for the lack of schema-level documentation.

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 the tool's function: 'Get or generate an investment memo for a deal.' It distinguishes between retrieval and generation with the `generate` flag, and the resource (memo for a deal) is specific. This uniquely differentiates it from sibling tools like `sieve_deals` or `sieve_screen`.

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 provides clear context for usage: it requires a completed screen and specifies that `deal_id` comes from `sieve_deals` or `sieve_screen`, implying the workflow. However, it does not explicitly state when not to use this tool or compare it to alternatives, which would merit a 5.

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