claude-skills-reference/c-level-advisor/executive-mentor/skills/challenge/SKILL.md

/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.