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

Annotations already declare readOnly, idempotent, non-destructive and closed-world, so the description only needs to add operational detail — and it does: ordering (newest first), the exact field set returned, that return is computed against the last close on file, and that a free account returns an empty list with an explanatory note. Pagination and size limits are the only gaps.

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?

Two sentences, front-loaded with the scope and ordering, then a compact enumeration of returned fields — which is necessary because there is no output schema. The field list is dense but each item earns its place; nothing is redundant.

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?

With no output schema, the description correctly carries the return shape, including derived values (unrealised return) and the thesis URL, plus empty-state behavior. Missing only pagination/row-limit behavior and how `book` interacts with the described cross-book scope.

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 single `book` parameter is fully documented in the schema with an enum, so the baseline is 3. The description does not mention the parameter at all and 'across the books this member holds' could be read as aggregating all books, leaving mild ambiguity about whether `book` filters or merely scopes the member's accounts.

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 resource and scope: 'every position the desk holds now across the books this member holds, newest first.' The word 'now' implicitly separates it from picks_closed, though no sibling is named explicitly. An agent can tell it retrieves current open positions rather than history.

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 only implied by 'now' versus the sibling picks_closed; no sentence says when to prefer this tool or what the `book` parameter should be set to. The free-account note gives useful context for an edge case but is not selection guidance.

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