challenge

---
name: challenge
description: Use before significant resource commitment, presenting to board/investors, or when feedback is one-sidedly positive. Pre-mortem analysis to uncover weaknesses and risks.
category: C-Level Advisory
version: 1.0.0
tools: []
---

# Pre-Mortem Plan Analysis

Systematically find weaknesses in any plan before reality does. Imagine the plan failed 12 months from now. Work backwards. Why?

## When to Run

- Before committing significant resources
- Before presenting to board or investors
- When you notice only positive feedback about the plan
- When the plan requires multiple external dependencies
- When there's pressure to move fast and "figure it out later"
- When you feel excited about the plan (signal to scrutinize harder)

## The Challenge Framework

### Step 1: Extract Core Assumptions
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, willingness to pay, buying cycle)
- Execution assumptions (team capacity, velocity, hiring needs)
- Customer assumptions (have problem, know they have it, will pay)
- Competitive assumptions (incumbents won't respond, no new entrant, moat holds)
- Financial assumptions (burn rate, revenue timing, CAC, LTV ratios)
- Dependency assumptions (partner delivery, API stability, regulation stability)

### Step 2: Rate Each Assumption

**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

Low/Unknown confidence × Critical/High impact = 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 because multiple assumptions have to be right simultaneously.
- 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 with zero slack?

### Step 5: Test the Reversibility

For each critical vulnerability: if 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 must validate before committing.

## The Hardest Questions

- 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?