Challenge

/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.

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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.

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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)

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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 Assumption

For every assumption extracted, rate it on two dimensions:

Confidence level (how sure are you this is true):

• High — verified with data, customer conversations, market research
• Medium — directionally right but not validated
• Low — plausible but untested
• Unknown — we simply don't know

Impact if wrong (what happens if this assumption fails):

• Critical — plan fails entirely
• High — major delay or cost overrun
• Medium — significant rework required
• Low — manageable adjustment

Step 3: Map Vulnerabilities

The matrix of Low/Unknown confidence × Critical/High impact = your highest-risk assumptions.

Vulnerability = Low confidence + High impact

These are not problems to ignore. They're the bets you're making. The question is: are you making them consciously?

Step 4: Find the Dependency Chain

Many plans fail not because any single assumption is wrong, but because multiple assumptions have to be right simultaneously.

Map the chain:

• Does assumption B depend on assumption A being true first?
• If the first thing goes wrong, how many downstream things break?
• What's the critical path? What has zero slack?

Step 5: Test the Reversibility

For each critical vulnerability: if this assumption turns out to be wrong at month 3, what do you do?

• Can you pivot?
• Can you cut scope?
• Is money already spent?
• Are commitments already made?

The less reversible, the more rigorously you need to validate before committing.

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