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

With no annotations, the description carries the disclosure burden and does a fair job: it states the proposal-then-ask-before-changing-anything approval behavior and describes the degraded path when no Planner is available. It stops short of saying what the plan does once approved or whether it is reversible.

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 action, but the sentence is long and the trailing 'Says where the plan is' is vague throat-clearing rather than a useful statement about the return.

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?

A one-parameter tool with full schema coverage, so it is nearly complete, but with no output schema the 'Says where the plan is' phrase leaves the response shape undefined, and the Caddie/Planner/Mac terminology assumes product knowledge the agent may not have.

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% for the single 'date' parameter (format, today-or-later, default today), so the schema does the work. The description never mentions the date parameter, adding nothing beyond the structured field.

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?

Names a specific action — running the 'Plan my day' Planner flow — and states the outcome (a proposed plan in the Planner's chat). It implicitly separates itself from generic agent tools like ask_agent by naming the Planner agent and the quick-plan fallback, though it never contrasts with a sibling explicitly.

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?

Usage context is only implied ('proposes a plan for the day'), and the parenthetical describes a runtime fallback rather than when an agent should pick this tool over ask_agent or agent_tasks. No exclusions or prerequisites are given.

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