assumption-challenger
Identify and challenge implicit assumptions in plans, proposals, and technical decisions. Use when strategic-cto-mentor needs to surface hidden assumptions and wishful thinking before they become costly mistakes.
git clone --depth 1 https://github.com/alirezarezvani/claude-cto-team /tmp/assumption-challenger && cp -r /tmp/assumption-challenger/skills/assumption-challenger ~/.claude/skills/assumption-challengerSKILL.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
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Detect common technical and organizational anti-patterns in proposals, architectures, and plans. Use when strategic-cto-mentor needs to identify red flags before they become problems.