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

Annotations already declare readOnlyHint=true, so the safe-read profile is covered. The description adds the return-content hint ('with the shifts and users involved') and the API endpoint, but does not describe default listing behavior when unfiltered, pagination semantics, or rate limits, so it adds some but not rich 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?

Front-loaded with the resource, then a compact enumeration of code meanings and the one cross-parameter constraint, ending with the endpoint. No filler sentences; every clause carries information.

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 9-parameter, no-required-parameter list tool with no output schema, the description covers the enum decoding and the start/end pairing rule that the schema states but does not explain. It leaves the unfiltered/default behavior and paging defaults unstated, which is a minor but real gap against no output 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 baseline would be 3, but the description meaningfully exceeds the schema by decoding numeric enum values the schema only labels generically ('One or more statuses' / 'One or more types'): status 0-5 and type 1/2/3. It also restates the start/end pairing rule. That decoding is genuine added value.

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?

States a specific verb ('List') and resource ('shift requests: swaps, drops and alerts') plus the scope of what is returned ('with the shifts and users involved'). This clearly distinguishes it from the sibling wheniwork_list_shifts and wheniwork_list_time_off_requests, and it even names the backing endpoint (GET /2/swaps).

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 is implied by the resource: you call this to enumerate swap/drop/alert requests. The only explicit guidance is the constraint that 'start and end must be given together'. It never states when to prefer this over a sibling or what happens if no filters are supplied, so guidance is only implicit.

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