Anti-Pattern Detector

Identifies recurring failure patterns in technical decisions, organizational structures, and project plans.

When to Use

• Reviewing architecture proposals
• Evaluating project plans and roadmaps
• Assessing team structures and processes
• Validating technology choices
• Checking migration strategies

Why Anti-Patterns Matter

Anti-patterns are proven failure modes. They look reasonable on the surface but lead to predictable problems:

• Technical debt accumulation
• Team burnout and turnover
• Missed deadlines and budgets
• System instability
• Organizational dysfunction

Detecting them early saves months of pain.

Anti-Pattern Categories

1. Architecture Anti-Patterns

Structural problems in system design.

2. Timeline Anti-Patterns

Planning failures that guarantee missed deadlines.

3. Team Anti-Patterns

Organizational structures that create dysfunction.

4. Process Anti-Patterns

Workflow failures that slow delivery.

5. Technology Anti-Patterns

Poor technology decisions.

Detection Process

Step 1: Scan for Signals

Look for these phrases that often indicate anti-patterns:

Timeline signals:

• "If everything goes well..."
• "We can do it faster if we're focused..."
• "Just need to hire..."
• "Should only take..."

Architecture signals:

• "We'll figure out the boundaries later..."
• "Everything talks to everything..."
• "It's only for now..."
• "We can always refactor..."

Team signals:

• "Only [person] knows..."
• "We'll hire for that..."
• "[Person] will handle all of..."
• "The team can absorb..."

Process signals:

• "We don't need docs for this..."
• "We'll add tests later..."
• "Let's discuss in the meeting..."
• "Requirements are still evolving..."

Step 2: Verify Pattern Match

For each suspected anti-pattern:

1. Identify the pattern: Which specific anti-pattern?
2. Gather evidence: What in the proposal matches?
3. Assess severity: How bad is it? (Critical/High/Medium/Low)
4. Check context: Could this be a reasonable exception?

Step 3: Document Findings

### Anti-Pattern: [Name]

**Category**: Architecture / Timeline / Team / Process / Technology
**Severity**: Critical / High / Medium / Low

**Evidence**:
- [Quote or observation 1]
- [Quote or observation 2]

**Why This Is a Problem**:
[Explain the typical failure mode]

**Historical Examples**:
[Reference similar failures if known]

**Recommendation**:
[Specific action to address]

Severity Framework

Critical

Will cause project failure if not addressed.

• Examples: No clear ownership, timeline fantasy for commitments, hero dependency
• Action: Stop and address before proceeding

High

Will cause significant problems.

• Examples: Premature microservices, understaffed plans, shiny object syndrome
• Action: Address in planning phase

Medium

Will cause friction and delays.

• Examples: Documentation gaps, process inefficiencies, minor scope creep
• Action: Include in risk mitigation

Low

Worth noting but manageable.

• Examples: Style inconsistencies, minor tech debt, preference-based choices
• Action: Track and address opportunistically

Output Format

# Anti-Pattern Analysis: [Plan/Proposal Name]

## Summary
- **Patterns Detected**: [Count]
- **Critical Issues**: [Count]
- **Overall Risk Level**: Critical / High / Medium / Low

## Critical Issues (Must Address)

### 1. [Pattern Name]
**Category**: [Category]
**Evidence**: [What triggered this detection]
**Risk**: [What will go wrong]
**Fix**: [How to address]

---

## High-Priority Issues (Should Address)

### 2. [Pattern Name]
[Same format]

---

## Medium-Priority Issues (Consider Addressing)

### 3. [Pattern Name]
[Same format]

---

## Patterns NOT Detected
[List patterns that were checked but not found - provides confidence]

## Recommendations

### Before Proceeding
1. [Critical action 1]
2. [Critical action 2]

### During Execution
1. [Mitigation 1]
2. [Mitigation 2]

### Monitoring
- [Warning sign to watch for]
- [Metric to track]

Common Pattern Combinations

Certain anti-patterns tend to appear together:

The Startup Death Spiral

• Timeline Fantasy + Understaffed Ambition + Hero Culture
• Result: Burnout, missed deadlines, key person leaves

The Enterprise Trap

• Analysis Paralysis + Documentation Theater + Meeting Madness
• Result: Nothing ships, team frustrated, competition wins

The Tech Debt Avalanche

• "We'll refactor later" + No clear ownership + Premature optimization
• Result: System becomes unmaintainable, rewrite required

The Microservices Mistake

• Premature Microservices + Distributed Monolith + Not enough DevOps
• Result: Complexity explosion, slower delivery than monolith

Integration with Validation

The antipattern-detector feeds into the broader validation workflow:

Proposal/Plan
     │
     ▼
[assumption-challenger] → Assumptions identified
     │
     ▼
[antipattern-detector] → Patterns identified
     │
     ▼
[validation-report-generator] → Combined 8-section report

References

• Anti-Pattern Catalog - Complete catalog with examples
• Challenge Questions - Questions to probe for patterns