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

Annotations already indicate read-only, idempotent, and non-destructive behavior. The description adds context about mode-specific behavior (e.g., 'team plans only' for team mode) and output format token savings. It does not mention rate limits or performance characteristics, but overall adds useful behavioral context.

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, with two focused paragraphs: one for modes and one for output formats. It front-loads the core purpose: 'Search workspace memory and knowledge.' Every sentence adds value without redundancy.

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 complexity (11 parameters, many modes) and lack of output schema, the description covers modes and output formats adequately but misses details on pagination, default behavior for 'include_memory', and how 'exact_match_boost' works. Schema fills some gaps, but description could be more comprehensive.

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 input schema has 100% description coverage, providing baseline. The tool description adds meaning beyond schema by explaining modes (e.g., 'meaning-based', 'exact match') and output format savings (e.g., '80% token savings'). This enriches the semantic understanding of parameters.

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 searches workspace memory and knowledge. It lists various modes and output formats, which adds specificity. However, it does not explicitly differentiate from sibling tools like 'tool_search' or memory-specific tools.

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 guidance on when to use each mode (e.g., 'auto recommended', 'keyword exact match'), which is helpful for mode selection. However, it lacks explicit guidance on when to use this search tool versus other available tools, such as memory retrieval or batch operations.

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