start_session

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

Discloses bootstrapping on first use and that without mode it returns a directive payload. No annotations provided, so description bears full burden. Lacks details on idempotency, side effects, or permissions required for a write operation.

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?

First sentence states purpose. Details follow logically: mode behavior, then stages/overrides format. Could be slightly more concise but is well-structured and front-loaded.

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?

Covers main behaviors and parameter formats. With output schema existing, return value documentation is sufficient. However, lacks explanation of bootstrapping implications and prerequisites. For a complex tool suite, more context on when to use vs siblings would improve 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?

With 0% schema coverage, description compensates by explaining that stages accepts JSON array or comma/newline list and overrides accepts JSON object or string form. Mode behavior is clarified. Question parameter is required but self-explanatory.

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?

Description clearly states 'Create a new session' and mentions bootstrapping the data store. It also describes behavior with/without mode. However, it does not explicitly differentiate from sibling tools like resume_session, which could be confused for session creation in some workflows.

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?

Provides guidance on when to include mode (to skip set_session_mode) and what happens without mode (returns directive payload). However, it does not mention when to use alternatives like resume_session for existing sessions or set_session_mode separately.

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