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assumption-challenger

The assumption-challenger identifies and systematically stress-tests unstated beliefs treated as facts in plans, proposals, and technical decisions. Use it when reviewing roadmaps, architecture proposals, resource allocations, timelines, and strategic initiatives to surface hidden assumptions about timelines, resources, technical capabilities, and business outcomes before they compound into costly failures.

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SKILL.md

# Assumption Challenger

Systematically identifies and stress-tests assumptions that are treated as facts but may not be validated.

## When to Use

- Validating roadmaps and project plans
- Reviewing architecture proposals
- Assessing build vs buy decisions
- Evaluating timelines and budgets
- Challenging strategic initiatives

## Why Assumptions Matter

Most project failures trace back to invalid assumptions:
- **Timeline assumptions**: "We can ship in 6 weeks" (based on nothing)
- **Resource assumptions**: "We'll hire 3 engineers" (in a tight market)
- **Technical assumptions**: "The API can handle 10K requests/sec" (never tested)
- **Business assumptions**: "Users will adopt this feature" (never validated)

**The cost of invalid assumptions compounds over time.** A bad assumption in week 1 can waste months of work.

---

## Assumption Categories

### 1. Timeline Assumptions
Assumptions about how long things will take.

**Common patterns**:
- "This should only take 2 weeks"
- "We'll have the integration done by launch"
- "The team can absorb this additional scope"

**Challenge questions**:
- What's this estimate based on? Past experience or hope?
- What similar work have we done? How long did it actually take?
- What's not included in this estimate? (Testing, documentation, deployment)
- What happens if this takes 2x longer?

### 2. Resource Assumptions
Assumptions about team capacity and availability.

**Common patterns**:
- "We'll hire 2 senior engineers by Q2"
- "The DevOps team can support this"
- "Sarah can lead this while maintaining her other work"

**Challenge questions**:
- What's the hiring timeline? What if we can't find the right people?
- What's the team's current utilization? Where does time come from?
- Who's the backup if the key person is unavailable?
- What happens if the team is 50% of expected capacity?

### 3. Technical Assumptions
Assumptions about system capabilities and constraints.

**Common patterns**:
- "The database can handle the load"
- "We can integrate with their API easily"
- "Our architecture supports this use case"

**Challenge questions**:
- Has this been tested at the required scale?
- What are the documented limits? What happens at those limits?
- What's the failure mode? How do we recover?
- Have we talked to the API provider about our usage patterns?

### 4. Business Assumptions
Assumptions about market, users, and business outcomes.

**Common patterns**:
- "Users want this feature"
- "This will reduce churn by 20%"
- "The market will wait for our solution"

**Challenge questions**:
- What evidence supports this? User research? Data?
- What if users don't adopt this? What's the fallback?
- What are competitors doing in this space?
- How will we know if this assumption is wrong?

### 5. External Assumptions
Assumptions about factors outside your control.

**Common patterns**:
- "The vendor will have the feature ready"
- "Regulations won't change"
- "The market will remain stable"

**Challenge questions**:
- What's our contingency if this doesn't happen?
- What's the vendor's track record on commitments?
- What early warning signs would indicate this is wrong?
- What's the cost of being wrong?

---

## Assumption Identification Process

### Step 1: Surface Assumptions

Read the proposal and identify statements that are treated as facts but aren't validated:

**Flag statements containing**:
- "We will..." (without evidence)
- "We can..." (without proof)
- "Users want..." (without data)
- "It should..." (without testing)
- "We expect..." (without basis)
- "We assume..." (at least they're honest)

### Step 2: Categorize Assumptions

For each assumption, categorize:

| Category | Risk if Wrong | Validation Difficulty |
|----------|---------------|----------------------|
| Timeline | Project delay | Medium (compare to past) |
| Resource | Execution failure | Medium (check market) |
| Technical | System failure | High (requires testing) |
| Business | Wasted investment | High (requires market validation) |
| External | Plans disrupted | Variable |

### Step 3: Assess Each Assumption

For each significant assumption:

```markdown
### Assumption: [Statement]

**Category**: [Type]
**Stated or Implicit**: [Was it stated or hidden?]

**Evidence Supporting**:
- [Evidence 1]
- [Evidence 2]

**Evidence Against**:
- [Counter-evidence 1]
- [Counter-evidence 2]

**Risk if Wrong**:
- [Impact on timeline]
- [Impact on cost]
- [Impact on success]

**Validation Method**:
- [How to test this assumption]
- [Cost/time to validate]

**Verdict**:
[ ] Valid - Evidence supports
[ ] Questionable - Needs validation
[ ] Invalid - Evidence contradicts
[ ] Unknown - Cannot assess
```

### Step 4: Prioritize Challenges

Focus on assumptions that are:
1. **High impact** - Project fails if wrong
2. **Low evidence** - Based on hope, not data
3. **Testable** - Can be validated before commitment

---

## Challenge Patterns

### The Reality Check
Compare assumption to external data.

**Template**:
> "You assume [X]. Industry data shows [Y]. What makes you different?"

**Example**:
> "You assume you can hire 3 senior engineers in 2 months. The average time-to-hire for senior engineers in your market is 4-6 months. What's your strategy to beat that?"

### The History Test
Compare to organization's past performance.

**Template**:
> "You assume [X]. Last time you attempted [similar thing], it took [Y]. What's changed?"

**Example**:
> "You assume 8 weeks for the microservices migration. Your last infrastructure migration took 5 months. What's different this time?"

### The Stress Test
Push assumption to failure point.

**Template**:
> "You assume [X]. What happens when [stress scenario]?"

**Example**:
> "You assume the system handles 10K concurrent users. What happens during a flash sale with 50K? What's the failure mode?"

### The Dependency Audit
Trace assumption to its dependencies.

**Template**:
> "For [assumption] to be true, what else must be true?"

**Example**:
> "For your 6-wee