challenge

name	challenge
description	Manage — /em -challenge — Pre-Mortem Plan Analysis
executor	LLM_BEHAVIOR
skill_id	business.c_level_advisor.executive_mentor.challenge
status	ADOPTED
security	{"level":"standard","pii":false,"approval_required":false}
anchors	["business"]
tier	2
input_schema	[{"name":"code_or_task","type":"string","description":"Code snippet, script, or task description to process","required":true}]
output_schema	[{"name":"report","type":"string","description":"Analysis report or summary from 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):

• — verified with data, customer conversations, market research