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/em:challenge — Pre-Mortem Plan Analysis · alirezarezvani | DecimalAI

productivityby alirezarezvani

/em:challenge — Pre-Mortem Plan Analysis

alirezarezvani/challenge

Source alirezarezvani/claude-skills ↗License MIT

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.

SkillScore74Maintained

Automatic

Project Management pack

Last verified 8/4/2026

What it changes

Passed 17 of 23 test cases with the skill, and 5 of 23 without it.

Without skill22%

With skill74%

Checks it passed that the model alone missed

The kill switches section contains explicit Continue if criteria.
Reversible bets are listed separately from irreversible commitments.
Kill switches evaluate plan progress at 30, 60, and 90 day intervals.

and 23 more in the full report

14 fixed3 passed either way4 still failing2 broke

Pass-rate lift: +52 pp
Tokens: +32%
Agent turns: 0%
Response time: -16%

Model gemini-3.6-flashMeasured 8/4/2026v117 of 23 cases passed with skill

Tokens, turns and time describe resource use, not a dollar price.

Use this skill

Save it into your project's skills folder. Claude Code picks it up in its next session.

curl -fsSL --create-dirs -o .claude/skills/alirezarezvani-challenge/SKILL.md https://app.decimal.ai/s/alirezarezvani-challenge/SKILL.md

Want it pinned and updatable? pip install "decimalai>=0.15", then decimalai skills add alirezarezvani-challenge, and start Claude Code with claude --plugin-dir "$(git rev-parse --show-toplevel)/.agents"

1 · One-time — install the CLI (docs ↗)

pip install "decimalai>=0.15"

2 · Get the skill — writes .agents/skills/alirezarezvani-challenge/ and pins it in .decimal/skills.lock

decimalai skills add alirezarezvani-challenge

No CLI? Get the same file — curl · raw file

curl -fsSL --create-dirs -o .claude/skills/alirezarezvani-challenge/SKILL.md https://app.decimal.ai/s/alirezarezvani-challenge/SKILL.md

Raw file: /s/alirezarezvani-challenge/SKILL.md ↗ · machine-readable summary at /s/alirezarezvani-challenge.json ↗

Safety checks: 3 of 3 passed

Code scan CleanIntent PassedContent Clean

See it in action

One of 14 test cases the skill fixed. Same model, same prompt, with and without the skill.

1 of 14

Prompt

Please challenge our operational hiring plan to scale our engineering department from 15 to 50 developers over two quarters. I want a structured pre-mortem report that outlines underlying execution assumptions evaluated by confidence and severity, isolates key plan vulnerabilities, charts out downstream dependency chains, categorizes reversible versus irreversible decisions, sets clear metric-based kill switches for pivoting, and provides concrete hardening actions to implement immediately.

What was checked, without and with the skill
Checked	Without skill	With skill
The report includes section headers for CORE ASSUMPTIONS, VULNERABILITY MAP, DEPENDENCY CHAIN, REVERSIBILITY ASSESSMENT, KILL SWITCHES, and HARDENING ACTIONS.	Passed	Passed
Assumptions are rated using Confidence and Impact categories rather than a numeric Risk Priority Number scale.	Passed	Passed
The dependency chain explicitly identifies the weakest link and its failure consequences.	Missed	Passed

case-03 · gemini-3.6-flash · 8/4/2026 · answers are capped and redacted

What's inside

The instructions your model reads when the skill loads.

SKILL.md176 linessingle file

/em:challenge — Pre-Mortem Plan Analysis

Command: /em:challenge <plan>

Systematically finds weaknesses in any plan before reality does. Not to kill the plan — to make it survive contact with reality.

The Core Idea

Most plans fail for predictable reasons. Not bad luck — bad assumptions. Overestimated demand. Underestimated complexity. Dependencies nobody questioned. Timing that made sense in a spreadsheet but not in the real world.

The pre-mortem technique: imagine it's 12 months from now and this plan failed spectacularly. Now work backwards. Why?

That's not pessimism. It's how you build something that doesn't collapse.

When to Run a Challenge

Before committing significant resources to a plan
Before presenting to the board or investors
When you notice you're only hearing positive feedback about the plan
When the plan requires multiple external dependencies to align
When there's pressure to move fast and "figure it out later"
When you feel excited about the plan (excitement is a signal to scrutinize harder)

The Challenge Framework

Step 1: Extract Core Assumptions

Before you can test a plan, you need to surface everything it assumes to be true.

For each section of the plan, ask:

What has to be true for this to work?
What are we assuming about customer behavior?
What are we assuming about competitor response?
What are we assuming about our own execution capability?
What external factors does this depend on?

Track record

Benchmark

17 / 23

test cases passed, vs 5 / 23 without

Adoption

Users: 0
Times used: 0

Safety and source details

SkillSafety

✓ 3 of 3 passed

Code scan15 of 15 checks clean

0 critical · 0 warning · 0 info — scanner v4 — 8/3/2026

View 15 scanner checks

live_secretremote_code_executionreverse_shelldata_exfiltrationssrf_metadataagent_snoopinganti_refusaldestructive_commandsobfuscated_unicodeunicode_homoglyphopaque_blobsuspicious_urltool_overreachtrigger_abuseprompt_injection_phrasing

IntentSafe

LLM judge · does the skill do what it claims

ContentClean

LLM judge · policy & harmful-content review

Source

Imported

alirezarezvani / claude-skills

.gemini/skills/challenge/SKILL.md

View on GitHub ↗

License MITImported 8/3/2026Version v1

Other skills for the same job

Published skills whose descriptions closely match this one, with their headline benchmark lift.

alirezarezvani/stress-test/em:stress-test — Business assumption stress testing. Use before betting on a plan whose core assumptions are unvalidated — e.g. stress-testing 'enterprise buyers will tolerate a 6-month pilot' or a hockey-stick revenue model.Close match+23 pp pass-rate lift

More skills from the same source and nearby in the registry, with their headline benchmark lift.

Ready to supercharge your AI agents?

See it in action

What's inside

/em:challenge — Pre-Mortem Plan Analysis

The Core Idea

When to Run a Challenge

The Challenge Framework

Step 1: Extract Core Assumptions

Track record

Benchmark

Adoption

SkillSafety

Source

Other skills for the same job

Related skills