Challenge Complexity

Evaluate the proposed solution for unnecessary complexity before committing to it.

Instructions

Consider the recent conversation history, your context, and the proposal to be evaluated.
Specific user instructions should be followed unless they are contradictory to the task at hand. $ARGUMENTS

Steps

Load — Use the Skill tool and load the outfitter:simplify skill
Consider — Ultrathink and analyze the proposal, identify initial complexity concerns
Dispatch or Execute — Choose execution path based on available tools:
- If Task tool available: Run the simplify loop (see below)
- If Task tool unavailable: Execute the complexity analysis methodology directly using the loaded skill

Simplify Loop (when Task tool available)

Run iterative cycles with a persistent skeptic agent until complexity is resolved:

┌─────────────────────────────────────────────────────────────┐
│  1. ANALYZE — Dispatch outfitter:skeptic                    │
│     └─ Examine proposal, identify complexity triggers,      │
│        generate alternatives, return structured findings    │
│                          ↓                                  │
│  2. PRESENT — Share findings with user                      │
│     └─ Escalation level, alternatives, probing questions    │
│                          ↓                                  │
│  3. DISCUSS — Gather user response                          │
│     └─ User provides context, answers questions,            │
│        or asks skeptic to dig deeper                        │
│                          ↓                                  │
│  4. EVALUATE — Determine next action                        │
│     └─ If resolved → Document decision                      │
│     └─ If more analysis needed → Resume skeptic (step 1)    │
└─────────────────────────────────────────────────────────────┘

Loop Execution

Initial dispatch — Pass proposal, context, requirements to skeptic
Retrieve results — Use TaskOutput to get structured JSON analysis
Present to user — Share escalation level, alternatives, and probing questions
Gather feedback — User may:
- Answer probing questions (pass answers back to skeptic)
- Ask skeptic to examine specific aspects deeper
- Accept an alternative and proceed
- Justify complexity with evidence (skeptic validates)
Resume or conclude:
- More analysis needed: Resume same skeptic agent with resume: {agentId} and new context
- Decision reached: Document outcome (proceed with simple, proceed with justified complexity, or revisit approach)

Resumable Skeptic Pattern

The skeptic maintains context across invocations via the resume parameter:

Initial dispatch:
  → skeptic analyzes proposal
  → returns findings + agentId: "abc123"

User provides additional context:
  → resume skeptic with { resume: "abc123" }
  → skeptic refines analysis with new information

User asks about specific concern:
  → resume skeptic with { resume: "abc123" }
  → skeptic digs deeper on that aspect

This preserves the skeptic's understanding of the proposal through multiple rounds of refinement.

The Framework

IDENTIFY — what complexity is being proposed?
ALTERNATIVE — what's the simplest thing that could work?
QUESTION — why isn't the simple approach sufficient?
DOCUMENT — if complexity is justified, record why

Context Handoff (for initial dispatch)

When dispatching to the skeptic subagent, include:

The proposed solution or approach
Current requirements and constraints
Any justifications already offered
Team/project context if relevant

When resuming the skeptic, include:

User's answers to probing questions
Additional context or constraints revealed
Specific areas to examine further
Evidence offered to justify complexity

Red Flag Rationalizations

Watch for these justifications — they usually indicate unjustified complexity:

"We might need this later"
"It's more flexible this way"
"This is how X company does it"
"It's the industry standard"
"We should do it right the first time"

Verdicts and Outcomes

The skeptic returns one of three verdicts:

Verdict	Meaning	Action
proceed	Complexity is minor (◇)	Note alternatives, continue
caution	Complexity is moderate (◆)	Discuss before proceeding
block	Complexity is high risk (◆◆)	Address concerns first

After discussion, document the outcome:

Simplified: Chose simpler alternative
Justified: Complexity validated with evidence, documented in ADR
Deferred: Needs more investigation, created follow-up task

The goal is NOT to reject all complexity — it's to ensure complexity is justified by evidence, not speculation.

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