Challenge
Pre-mortem plan analysis.
Before & after
Same prompt, same agent — the only difference is the skill.
Your launch plan sounds solid. Before you go all-in, it's good to think about what could go wrong. You should consider your assumptions—things you believe are true but haven't tested. You should also think about dependencies—what needs to happen first for the rest to work. And of course, there are always execution risks—things that seem simple but turn out to be harder than expected. If you can identify these ahead of time, you'll be better positioned to handle them. Why don't you walk me through the plan, and I can help you think through potential issues?
PRE-MORTEM: PRODUCT LAUNCH PLAN Prompt: "Imagine it's 6 months from now and the launch failed. Work backwards to find what broke." CRITICAL ASSUMPTIONS (Unvalidated) 1. "Sales will close 10 pilots in first month" ⚠ Assumption unchecked: Are 10 target accounts even aware of us? Who drives buying decisions? Risk: Real close rate is 2-3 (70% miss); launch delays 3 months; investor pressure Mitigation: Pre-launch 5 inbound calls with target buyers; validate problem severity (if fake, drop plan) 2. "Product is feature-complete for launch" ⚠ Assumption unchecked: What feature is minimum viable? Who defines done? Risk: Marketing says "30 features ready"; engineering says "5 are shippable"; mismatch = embarrassment Mitigation: Scorecard: 5 core features must hit 95% performance + zero data loss before launch date CRITICAL DEPENDENCIES (Bottlenecks) 1. Data migration (old system → new platform) Risk: If 1 month late, launch slips 1 month (non-negotiable dependency) Mitigation: Migration starts 4 weeks before launch (not day-of); test with 20% of data first 2. Sales team onboarding Risk: If sales only trained 1 week before, they'll fumble messaging; deal close rate drops 40% Mitigation: Sales training starts 4 weeks early; run 3 practice pitches per rep EXECUTION RISKS (Things that sound easy but aren't) 1. Marketing collateral approval cycles (design → legal → CMO → final) Risk: Typical cycle = 3 weeks; if one stakeholder missing, delays 5+ days Mitigation: Get sign-offs in writing 4 weeks before; escalate early 2. Customer support readiness (documentation, ticketing system, first-call scripts) Risk: If support unprepared, 1st customer issue bounces 3x; reputation hit Mitigation: Support runs dry-runs with real scenarios 2 weeks before launch RECOMMENDATION Top 3 actions: (1) Validate problem with 5 buyers NOW; (2) Define 5 core features + freeze scope 4 weeks before; (3) Start migration + sales training 4 weeks out. Compress timelines now so dependencies don't slip. If any buyer validation fails, consider delaying launch 2-4 weeks instead of shipping broken.
About this skill
name: challenge description: Use when Pre-mortem plan analysis.
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.
What you get
- Public GitHub repo (alirezarezvani/claude-skills)
- the challenge skill folder with SKILL.md. Part of a 337-skill / 30-agent / 70-command install.
Customize your output
- Fork the repo and adapt the skill's instructions and references to your workflow.
Example output
Activates automatically when your request matches Challenge; chains with the other skills, agents, and commands in the collection.
Best for
Creators, builders, and teams using Claude Code.
SKILL.md preview
---
name: challenge
description: Use this skill when a plan needs a pre-mortem pass before significant resource commitment, especially when feedback so far has been one-sidedly positive.
version: 1.0.0
category: Business & Ops / Executive Advisory
author: AgentVolt
license: proprietary
tags:
- business-ops
- executive-advisory
---
# Challenge
Imagines the plan has already failed twelve months from now and works backward to surface the assumptions, dependencies, and execution risks that caused it, before real resources are committed.
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