Agent skill · product strategy · alirezarezvani
challenge
Pre-mortem a plan: assume it failed in 12 months and work back to the assumptions, dependencies and execution risks. Use whenever the user will commit serious resources or feedback seems too positive.
Why this skill is useful
Provides a structured framework for identifying and analyzing assumptions and risks in strategic planning, which the AI may not generate independently.
What it needs
About 4k tokens when loaded. Last updated 2026-08-05. 23,939 stars on the source repository.
What this skill does
/executive-mentor:challenge — Pre-Mortem Plan Analysis Command: /executive-mentor: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? Common assumption categories: Market assumptions — size, growth rate, customer willingness to pay, buying cycle Execution assumptions — team capacity, velocity, no major hires needed Customer assumptions — they have the problem, they know they have it, they'll pay to solve it Competitive assumptions — incumbents won't respond, no new entrant, moat holds Financial assumptions — burn rate, revenue timing, CAC, LTV ratios Dependency assumptions — partner will deliver, API won't change, regulations won't shift Step 2: Rate Each As …
How to use it
Reference it in AdaL, Claude Code, Cursor or any coding agent — nothing to install:
@skills alirezarezvani/challenge--381b8d