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challenge

Pre-mortem plan analysis. Imagine the plan failed 12 months from now and work backwards to find the weaknesses. Surfaces assumptions, dependencies, and execution risks before committing resources. Use when before significant resource commitment, before presenting to a board or investors, when feedback has been one-sidedly positive, or when there is pressure to move fast and figure it out later.

65

Quality

82%

Does it follow best practices?

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SKILL.md
Quality
Evals
Security

Quality

Content

67%Weight 40%Scale 1-5

Reviews the quality of instructions and guidance provided to agents. Good implementation is clear, handles edge cases, and produces reliable results.

A well-structured instruction-only skill: the five-step framework, rating scales, and output template give Claude concrete, executable guidance, and the section organization is clean. The main costs are rhetorical padding and a redundant explanation of the pre-mortem concept, plus implicit mapping between the rating step and the report's risk buckets.

Suggestions

Trim the motivational asides ('That's not pessimism...', 'These are not problems to ignore...', 'Unknown risks are dangerous...') and condense the 'Core Idea' section to one or two lines — Claude already knows what a pre-mortem is; only the specific application recipe is new information.

Make the bridge from Step 2 ratings to the report's 'Critical risks' / 'High risks' buckets explicit (e.g., state the rule mapping confidence x impact combinations to each bucket) so the output is deterministic.

Add a short worked example (a few assumptions extracted from a sample plan, rated and bucketed) to make the output template fully copy-paste ready.

DimensionReasoningScore

Conciseness

The 'Core Idea' section re-explains the pre-mortem technique Claude already knows, and motivational asides recur throughout ('That's not pessimism. It's how you build something that doesn't collapse.', 'Unknown risks are dangerous. Known risks are manageable.'). The framework content itself is efficient, so this sits at 'mostly efficient but could be tightened' rather than 'noticeably verbose'.

3 / 5

Actionability

Concrete rating scales (High/Medium/Low/Unknown confidence, Critical/High/Medium/Low impact), a copy-paste fill-in output template, per-plan-type question lists, and 30/60/90-day kill-switch criteria make the guidance mostly executable. No worked example applying the framework to a sample plan keeps it below fully-executable coverage of common cases.

4 / 5

Workflow Clarity

A clear five-step sequence (extract assumptions, rate, map vulnerabilities, dependency chain, reversibility) culminating in a defined output format. Validation checkpoints are implicit — e.g., how confidence/impact ratings map into the Critical vs. High report buckets is not spelled out, and there is no step verifying every extracted assumption got rated — so it falls short of the explicit-validation anchor.

4 / 5

Progressive Disclosure

A single-file skill (no references/, scripts/, or assets/ exist) with well-organized sections and logical flow; nothing is inlined that clearly belongs elsewhere. It exceeds the under-50-line simple-skill threshold and has no one-level-deep references (the patterns-by-plan-type section is a natural split candidate if the skill grows), so it does not reach the top anchor.

4 / 5

Total

15

/

20

Passed

Description

87%Weight 40%Scale 1-5

Based on the skill's description, can an agent find and select it at the right time? Clear, specific descriptions lead to better discovery.

A strong description: it names the technique and its outputs, and pairs them with an explicit, concrete multi-scenario 'Use when' clause. The only gaps are a handful of missing natural synonyms ('stress test', 'red team') that users might use to invoke this skill.

DimensionReasoningScore

Specificity

Names the domain ('Pre-mortem plan analysis') and several concrete actions ('work backwards to find the weaknesses', 'Surfaces assumptions, dependencies, and execution risks'), but stays at the capability level without naming the concrete deliverables (vulnerability map, kill switches) that the body defines — minor gaps rather than comprehensive coverage.

4 / 5

Completeness

Explicitly answers both what ('Pre-mortem plan analysis... Surfaces assumptions, dependencies, and execution risks') and when ('Use when before significant resource commitment, before presenting to a board or investors, when feedback has been one-sidedly positive, or when there is pressure to move fast') with concrete, multi-scenario trigger phrases — matches the anchor-5 example structure exactly.

5 / 5

Trigger Term Quality

Good natural-term coverage: 'pre-mortem', 'weaknesses', 'assumptions', 'dependencies', 'execution risks', 'board or investors', 'pressure to move fast'. A few natural synonyms users might say ('stress test', 'red team', 'poke holes') are missing, so not 5; coverage is clearly beyond the some-keywords level, so not 3.

4 / 5

Distinctiveness Conflict Risk

'Pre-mortem' plus specific triggers like 'before presenting to a board or investors' and 'feedback has been one-sidedly positive' carve a clear niche with distinct triggers and minimal conflict risk against generic review or planning skills.

5 / 5

Total

18

/

20

Passed

Validation

100%

Checks the skill against the spec for correct structure and formatting. All validation checks must pass before discovery and implementation can be scored.

Validation — 16 / 16 Passed

Validation for skill structure

No warnings or errors.

Repository

alirezarezvani/claude-skills

Path

c-level-advisor/executive-mentor/skills/challenge/SKILL.md

Reviewed

Table of Contents

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