Anti-Pattern Detector Skill

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.

| 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 |

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:

Identify the pattern: Which specific anti-pattern?
Gather evidence: What in the proposal matches?
Assess severity: How bad is it? (Critical/High/Medium/Low)
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

Agent Skills: Anti-Pattern Detector

Skill Files