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name: antipattern-detector description: 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.

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.

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Anti-Pattern Categories

1. Architecture Anti-Patterns

Structural problems in system design.

Pattern	Description	Symptoms
Big Ball of Mud	No clear architecture, everything coupled	Can't change X without breaking Y
Golden Hammer	Using one tech for everything	"We'll use Kubernetes for that too"
Premature Microservices	Splitting before understanding boundaries	3 devs managing 20 services
Distributed Monolith	Microservices with tight coupling	Deploy all services together
Resume-Driven Development	Tech choices for career, not product	"Let's use Rust for the admin panel"

2. Timeline Anti-Patterns

Planning failures that guarantee missed deadlines.

Pattern	Description	Symptoms
Timeline Fantasy	Optimistic estimates ignoring reality	"6 weeks if everything goes well"
Scope Creep Blindness	Not accounting for inevitable additions	Same deadline, 2x features
Parallel Path Delusion	Assuming unlimited parallelization	"Add more devs to go faster"
MVP Maximalism	MVP that's actually V3	47 features in "minimum" product
Demo-Driven Development	Building for demos, not production	"It works on my machine"

3. Team Anti-Patterns

Organizational structures that create dysfunction.

Pattern	Description	Symptoms
Hero Culture	Reliance on key individuals	"Only Sarah can fix that"
Knowledge Silos	Critical info in one person's head	Bus factor of 1
Conway's Law Violation	Architecture doesn't match team structure	Team boundaries ≠ service boundaries
Understaffed Ambition	Big plans with tiny teams	2 devs building "the platform"
Absent Ownership	No clear owner for components	Bugs fall through cracks

4. Process Anti-Patterns

Workflow failures that slow delivery.

Pattern	Description	Symptoms
Cargo Cult Agile	Agile ceremonies without principles	Standups but no shipping
Analysis Paralysis	Over-planning, under-executing	Month 3 of "finalizing requirements"
Infinite Refactoring	Never shipping, always "improving"	"One more cleanup before release"
Documentation Theater	Docs that no one reads or maintains	200-page spec, outdated day 1
Meeting Madness	More meetings than coding time	"Let's schedule a meeting to discuss"

5. Technology Anti-Patterns

Poor technology decisions.

Pattern	Description	Symptoms
Shiny Object Syndrome	Chasing latest tech without reason	"We should rewrite in [new thing]"
Not Invented Here	Building what should be bought	Custom auth, custom logging, custom everything
Vendor Lock-in Denial	Ignoring exit costs	"We can always migrate later"
Premature Optimization	Optimizing before measuring	Caching layer with 10 users
Framework Overload	Too many frameworks/libraries	47 npm dependencies for a button

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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]

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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

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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]

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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

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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

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References

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