Conciseness

The ~30-line body is lean, assumes Claude's competence, and contains no concept explanations or padding — every section carries information. It misses anchor 5 only because the Execution Checklist partly restates the When To Use bullets (items 2-3 restate the cli_agent and init bullets), a minor redundancy that could be trimmed.

Actionability

The body names real subcommands ("planoai up", "planoai cli_agent", "planoai init") but never shows a single executable command, example, or syntax — it even instructs Claude to "Provide a compact runbook with exact CLI commands" without supplying any. "Follow startup validation order" references an order that is never defined. This matches anchor 2 (minimal concrete guidance; high-level hints missing the specific steps), not anchor 3, because nothing here can be executed or followed concretely.

Workflow Clarity

The Execution Checklist is numbered but is a list of principles rather than a processable sequence: "Follow startup validation order before deep debugging" is undefined, and there are no validation checkpoints or error-recovery steps anywhere. This fits anchor 2 (rough sequence present but many gaps; steps poorly defined; validation absent) better than anchor 3, whose steps at least map to a real sequence of operations.

Progressive Disclosure

The "Apply These Rules" section lists rule names (`cli-startup`, `cli-agent`, `cli-init`) but no bundle files exist — there are no references/, scripts/, or assets/ directories — so those references are dangling and the actual operational content is unreachable. Sections themselves are organized, but per the guideline to score against the actual bundle structure, references pointing at nonexistent content score at anchor 2 (minimal structure; references are buried/broken) rather than 3.

Specificity

The description names a concrete domain ("Plano CLI") and lists three task areas ("startup troubleshooting, cli_agent workflows, and template-based project bootstrapping"), but the leading action "Apply Plano CLI best practices" is generic — it describes areas of coverage rather than specific actions. This matches anchor 3 (names domain and 1-2 concrete actions, not comprehensive) and falls short of anchor 4, which expects several specific actions like 'Extracts text..., fills forms, converts...'.

Completeness

Both parts are present: the 'what' is "Apply Plano CLI best practices" and an explicit 'when' clause exists ("Use for startup troubleshooting, cli_agent workflows, and template-based project bootstrapping"). This earns anchor 4 rather than 5 because the 'what' is vague — 'apply best practices' does not state what the skill actually does — and the 'when' clause names categories rather than concrete trigger phrases.

Trigger Term Quality

"startup troubleshooting" and "template-based project bootstrapping" are reasonable natural phrases, but the description misses the actual commands users would type ("planoai up", "planoai init") and common variations like "planoai". Anchor 3 (some relevant keywords but missing common variations or synonyms) fits better than anchor 4, since the most natural trigger terms a Plano user would say are absent.

Distinctiveness Conflict Risk

The Plano CLI niche ("cli_agent workflows", "Plano") is clearly distinct from generic CLI or document skills, giving minimal conflict risk. It does not reach anchor 5 only because "startup troubleshooting" alone is somewhat generic and the description omits the distinctive 'planoai' command names that would fully seal the niche.