neekware /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?
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.
Output Format
Challenge Report: [Plan Name]
CORE ASSUMPTIONS (extracted)
1. [Assumption] — Confidence: [H/M/L/?] — Impact if wrong: [Critical/High/Medium/Low]
2. ...
VULNERABILITY MAP
Critical risks (act before proceeding):
• [#N] [Assumption] — WHY it might be wrong — WHAT breaks if it is
High risks (validate before scaling):
• ...
DEPENDENCY CHAIN
[Assumption A] → depends on → [Assumption B] → which enables → [Assumption C]
Weakest link: [X] — if this breaks, [Y] and [Z] also fail
REVERSIBILITY ASSESSMENT
• Reversible bets: [list]
• Irreversible commitments: [list — treat with extreme care]
KILL SWITCHES
What would have to be true at [30/60/90 days] to continue vs. kill/pivot?
• Continue if: ...
• Kill/pivot if: ...
HARDENING ACTIONS
1. [Specific validation to do before proceeding]
2. [Alternative approach to consider]
3. [Contingency to build into the plan]
Challenge Patterns by Plan Type
Product Roadmap
- Are we building what customers will pay for, or what they said they wanted?
- Does the velocity estimate account for real team capacity (not theoretical)?
- What happens if the anchor feature takes 3× longer than estimated?
- Who owns decisions when requirements conflict?
Go-to-Market Plan
- What's the actual ICP conversion rate, not the hoped-for one?
- How many touches to close, and do you have the sales capacity for that?
- What happens if the first 10 deals take 3 months instead of 1?
- Is "land and expand" a real motion or a hope?
Hiring Plan
- What happens if the key hire takes 4 months to find, not 6 weeks?
- Is the plan dependent on retaining specific people who might leave?
- Does the plan account for ramp time (usually 3–6 months before full productivity)?
- What's the burn impact if headcount leads revenue by 6 months?
Fundraising Plan
- What's your fallback if the lead investor passes?
- Have you modeled the timeline if it takes 6 months, not 3?
- What's your runway at current burn if the round closes at the low end?
- What assumptions break if you raise 50% of the target amount?
The Hardest Questions
These are the ones people skip:
- "What's the bear case, not the base case?"
- "If this exact plan was run by a team we don't trust, would it work?"
- "What are we not saying out loud because it's uncomfortable?"
- "Who has incentives to make this plan sound better than it is?"
- "What would an enemy of this plan attack first?"
Deliverable
The output of /em:challenge is not permission to stop. It's a vulnerability map. Now you can make conscious decisions: validate the risky assumptions, hedge the critical ones, or accept the bets you're making knowingly.
Unknown risks are dangerous. Known risks are manageable.