deep-interview

Deep Interview implements Ouroboros-inspired Socratic questioning with mathematical ambiguity scoring. It replaces vague ideas with crystal-clear specifications by asking targeted questions that expose hidden assumptions, measuring clarity across weighted dimensions, and refusing to proceed until ambiguity drops below a configurable threshold (default: 20%). The output feeds into a 3-stage pipeline: **deep-interview → ralplan (consensus refinement) → autopilot (execution)**, ensuring maximum clarity at every stage.

<Use_When>

• User has a vague idea and wants thorough requirements gathering before execution
• User says "deep interview", "interview me", "ask me everything", "don't assume", "make sure you understand"
• User says "ouroboros", "socratic", "I have a vague idea", "not sure exactly what I want"
• User wants to avoid "that's not what I meant" outcomes from autonomous execution
• Task is complex enough that jumping to code would waste cycles on scope discovery
• User wants mathematically-validated clarity before committing to execution </Use_When>

<Do_Not_Use_When>

• User has a detailed, specific request with file paths, function names, or acceptance criteria -- execute directly
• User wants to explore options or brainstorm -- use omc-plan skill instead
• User wants a quick fix or single change -- delegate to executor or ralph
• User says "just do it" or "skip the questions" -- respect their intent
• User already has a PRD or plan file -- use ralph or autopilot with that plan </Do_Not_Use_When>

<Why_This_Exists> AI can build anything. The hard part is knowing what to build. OMC's autopilot Phase 0 expands ideas into specs via analyst + architect, but this single-pass approach struggles with genuinely vague inputs. It asks "what do you want?" instead of "what are you assuming?" Deep Interview applies Socratic methodology to iteratively expose assumptions and mathematically gate readiness, ensuring the AI has genuine clarity before spending execution cycles.

Inspired by the Ouroboros project which demonstrated that specification quality is the primary bottleneck in AI-assisted development. </Why_This_Exists>

<Execution_Policy>

• Ask ONE question at a time -- never batch multiple questions
• Target the WEAKEST clarity dimension with each question
• Gather codebase facts via explore agent BEFORE asking the user about them
• Score ambiguity after every answer -- display the score transparently
• Do not proceed to execution until ambiguity ≤ threshold (default 0.2)
• Allow early exit with a clear warning if ambiguity is still high
• Persist interview state for resume across session interruptions
• Challenge agents activate at specific round thresholds to shift perspective </Execution_Policy>

Phase 1: Initialize

1. Parse the user's idea from {{ARGUMENTS}}
2. Detect brownfield vs greenfield:
   • Run explore agent (haiku): check if cwd has existing source code, package files, or git history
   • If source files exist AND the user's idea references modifying/extending something: brownfield
   • Otherwise: greenfield
3. For brownfield: Run explore agent to map relevant codebase areas, store as codebase_context
4. Initialize state via state_write(mode="deep-interview"):

{
  "active": true,
  "current_phase": "deep-interview",
  "state": {
    "interview_id": "<uuid>",
    "type": "greenfield|brownfield",
    "initial_idea": "<user input>",
    "rounds": [],
    "current_ambiguity": 1.0,
    "threshold": 0.2,
    "codebase_context": null,
    "challenge_modes_used": []
  }
}

5. Announce the interview to the user:

Starting deep interview. I'll ask targeted questions to understand your idea thoroughly before building anything. After each answer, I'll show your clarity score. We'll proceed to execution once ambiguity drops below 20%.

Your idea: "{initial_idea}" Project type: {greenfield|brownfield} Current ambiguity: 100% (we haven't started yet)

Phase 2: Interview Loop

Repeat until ambiguity ≤ threshold OR user exits early:

Step 2a: Generate Next Question

Build the question generation prompt with:

• The user's original idea
• All prior Q&A rounds (conversation history)
• Current clarity scores per dimension (which is weakest?)
• Challenge agent mode (if activated -- see Phase 3)
• Brownfield codebase context (if applicable)

Question targeting strategy:

• Identify the dimension with the LOWEST clarity score
• Generate a question that specifically improves that dimension
• Questions should expose ASSUMPTIONS, not gather feature lists

Question styles by dimension:

Dimension	Question Style	Example
Goal Clarity	"What exactly happens when...?"	"When you say 'manage tasks', what specific action does a user take first?"
Constraint Clarity	"What are the boundaries?"	"Should this work offline, or is internet connectivity assumed?"
Success Criteria	"How do we know it works?"	"If I showed you the finished product, what would make you say 'yes, that's it'?"
Context Clarity (brownfield)	"How does this fit?"	"The existing auth uses JWT in src/auth/. Should we extend that or add a separate flow?"

Step 2b: Ask the Question

Use AskUserQuestion with the generated question. Present it clearly with the current ambiguity context:

Round {n} | Targeting: {weakest_dimension} | Ambiguity: {score}%

{question}

Options should include contextually relevant choices plus free-text.

Step 2c: Score Ambiguity

After receiving the user's answer, score clarity across all dimensions.

Scoring prompt (use opus model, temperature 0.1 for consistency):

Given the following interview transcript for a {greenfield|brownfield} project, score clarity on each dimension from 0.0 to 1.0:

Original idea: {idea}

Transcript:
{all rounds Q&A}

Score each dimension:
1. Goal Clarity (0.0-1.0): Is the primary objective unambiguous? Can you state it in one sentence without qualifiers?
2. Constraint Clarity (0.0-1.0): Are the boundaries, limitations, and non-goals clear?
3. Success Criteria Clarity (0.0-1.0): Could you write a test that verifies success? Are acceptance criteria concrete?
{4. Context Clarity (0.0-1.0): [brownfield only] Do we understand the existing system well enough to modify it safely?}

For each dimension provide:
- score: float (0.0-1.0)
- justification: one sentence explaining the score
- gap: what's still unclear (if score < 0.9)

Respond as JSON.

Calculate ambiguity:

Greenfield: ambiguity = 1 - (goal × 0.40 + constraints × 0.30 + criteria × 0.30) Brownfield: ambiguity = 1 - (goal × 0.35 + constraints × 0.25 + criteria × 0.25 + context × 0.15)

Step 2d: Report Progress

After scoring, show the user their progress:

Round {n} complete.

| Dimension | Score | Weight | Weighted | Gap |
|-----------|-------|--------|----------|-----|
| Goal | {s} | {w} | {s*w} | {gap or "Clear"} |
| Constraints | {s} | {w} | {s*w} | {gap or "Clear"} |
| Success Criteria | {s} | {w} | {s*w} | {gap or "Clear"} |
| Context (brownfield) | {s} | {w} | {s*w} | {gap or "Clear"} |
| **Ambiguity** | | | **{score}%** | |

{score <= threshold ? "Clarity threshold met! Ready to proceed." : "Focusing next question on: {weakest_dimension}"}

Step 2e: Update State

Update interview state with the new round and scores via state_write.

Step 2f: Check Soft Limits

• Round 3+: Allow early exit if user says "enough", "let's go", "build it"
• Round 10: Show soft warning: "We're at 10 rounds. Current ambiguity: {score}%. Continue or proceed with current clarity?"
• Round 20: Hard cap: "Maximum interview rounds reached. Proceeding with current clarity level ({score}%)."

Phase 3: Challenge Agents

At specific round thresholds, shift the questioning perspective:

Round 4+: Contrarian Mode

Inject into the question generation prompt:

You are now in CONTRARIAN mode. Your next question should challenge the user's core assumption. Ask "What if the opposite were true?" or "What if this constraint doesn't actually exist?" The goal is to test whether the user's framing is correct or just habitual.

Round 6+: Simplifier Mode

Inject into the question generation prompt:

You are now in SIMPLIFIER mode. Your next question should probe whether complexity can be removed. Ask "What's the simplest version that would still be valuable?" or "Which of these constraints are actually necessary vs. assumed?" The goal is to find the minimal viable specification.

Round 8+: Ontologist Mode (if ambiguity still > 0.3)

Inject into the question generation prompt:

You are now in ONTOLOGIST mode. The ambiguity is still high after 8 rounds, suggesting we may be addressing symptoms rather than the core problem. Ask "What IS this, really?" or "If you could only describe this in one sentence to a colleague, what would you say?" The goal is to find the essence.

Challenge modes are used ONCE each, then return to normal Socratic questioning. Track which modes have been used in state.

Phase 4: Crystallize Spec

When ambiguity ≤ threshold (or hard cap / early exit):

1. Generate the specification using opus model with the full interview transcript
2. Write to file: .omc/specs/deep-interview-{slug}.md

Spec structure:

# Deep Interview Spec: {title}

## Metadata
- Interview ID: {uuid}
- Rounds: {count}
- Final Ambiguity Score: {score}%
- Type: greenfield | brownfield
- Generated: {timestamp}
- Threshold: {threshold}
- Status: {PASSED | BELOW_THRESHOLD_EARLY_EXIT}

## Clarity Breakdown
| Dimension | Score | Weight | Weighted |
|-----------|-------|--------|----------|
| Goal Clarity | {s} | {w} | {s*w} |
| Constraint Clarity | {s} | {w} | {s*w} |
| Success Criteria | {s} | {w} | {s*w} |
| Context Clarity | {s} | {w} | {s*w} |
| **Total Clarity** | | | **{total}** |
| **Ambiguity** | | | **{1-total}** |

## Goal
{crystal-clear goal statement derived from interview}

## Constraints
- {constraint 1}
- {constraint 2}
- ...

## Non-Goals
- {explicitly excluded scope 1}
- {explicitly excluded scope 2}

## Acceptance Criteria
- [ ] {testable criterion 1}
- [ ] {testable criterion 2}
- [ ] {testable criterion 3}
- ...

## Assumptions Exposed & Resolved
| Assumption | Challenge | Resolution |
|------------|-----------|------------|
| {assumption} | {how it was questioned} | {what was decided} |

## Technical Context
{brownfield: relevant codebase findings from explore agent}
{greenfield: technology choices and constraints}

## Ontology (Key Entities)
| Entity | Fields | Relationships |
|--------|--------|---------------|
| {entity} | {field1, field2} | {relates to...} |

## Interview Transcript
<details>
<summary>Full Q&A ({n} rounds)</summary>

### Round 1
**Q:** {question}
**A:** {answer}
**Ambiguity:** {score}% (Goal: {g}, Constraints: {c}, Criteria: {cr})

...
</details>

Phase 5: Execution Bridge

After the spec is written, present execution options via AskUserQuestion:

Question: "Your spec is ready (ambiguity: {score}%). How would you like to proceed?"

Options:

1. Ralplan → Autopilot (Recommended)

   • Description: "3-stage pipeline: consensus-refine this spec with Planner/Architect/Critic, then execute with full autopilot. Maximum quality."
   • Action: Invoke Skill("oh-my-claudecode:omc-plan") with --consensus --direct flags and the spec file path as context. The --direct flag skips the omc-plan skill's interview phase (the deep interview already gathered requirements), while --consensus triggers the Planner/Architect/Critic loop. When consensus completes and produces a plan in .omc/plans/, invoke Skill("oh-my-claudecode:autopilot") with the consensus plan as Phase 0+1 output — autopilot skips both Expansion and Planning, starting directly at Phase 2 (Execution).
   • Pipeline: deep-interview spec → omc-plan --consensus --direct → autopilot execution

2. Execute with autopilot (skip ralplan)

   • Description: "Full autonomous pipeline — planning, parallel implementation, QA, validation. Faster but without consensus refinement."
   • Action: Invoke Skill("oh-my-claudecode:autopilot") with the spec file path as context. The spec replaces autopilot's Phase 0 — autopilot starts at Phase 1 (Planning).

3. Execute with ralph

   • Description: "Persistence loop with architect verification — keeps working until all acceptance criteria pass"
   • Action: Invoke Skill("oh-my-claudecode:ralph") with the spec file path as the task definition.

4. Execute with team

   • Description: "N coordinated parallel agents — fastest execution for large specs"
   • Action: Invoke Skill("oh-my-claudecode:team") with the spec file path as the shared plan.

5. Refine further

   • Description: "Continue interviewing to improve clarity (current: {score}%)"
   • Action: Return to Phase 2 interview loop.

IMPORTANT: On execution selection, MUST invoke the chosen skill via Skill(). Do NOT implement directly. The deep-interview agent is a requirements agent, not an execution agent.

The 3-Stage Pipeline (Recommended Path)

Stage 1: Deep Interview          Stage 2: Ralplan                Stage 3: Autopilot
┌─────────────────────┐    ┌───────────────────────────┐    ┌──────────────────────┐
│ Socratic Q&A        │    │ Planner creates plan      │    │ Phase 2: Execution   │
│ Ambiguity scoring   │───>│ Architect reviews         │───>│ Phase 3: QA cycling  │
│ Challenge agents    │    │ Critic validates          │    │ Phase 4: Validation  │
│ Spec crystallization│    │ Loop until consensus      │    │ Phase 5: Cleanup     │
│ Gate: ≤20% ambiguity│    │ ADR + RALPLAN-DR summary  │    │                      │
└─────────────────────┘    └───────────────────────────┘    └──────────────────────┘
Output: spec.md            Output: consensus-plan.md        Output: working code

Why 3 stages? Each stage provides a different quality gate:

1. Deep Interview gates on clarity — does the user know what they want?
2. Ralplan gates on feasibility — is the approach architecturally sound?
3. Autopilot gates on correctness — does the code work and pass review?

Skipping any stage is possible but reduces quality assurance:

• Skip Stage 1 → autopilot may build the wrong thing (vague requirements)
• Skip Stage 2 → autopilot may plan poorly (no Architect/Critic challenge)
• Skip Stage 3 → no execution (just a refined plan)

<Tool_Usage>

• Use AskUserQuestion for each interview question — provides clickable UI with contextual options
• Use Task(subagent_type="oh-my-claudecode:explore", model="haiku") for brownfield codebase exploration (run BEFORE asking user about codebase)
• Use opus model (temperature 0.1) for ambiguity scoring — consistency is critical
• Use state_write / state_read for interview state persistence
• Use Write tool to save the final spec to .omc/specs/
• Use Skill() to bridge to execution modes — never implement directly
• Challenge agent modes are prompt injections, not separate agent spawns </Tool_Usage>

Targeting weakest dimension: ``` Scores: Goal=0.9, Constraints=0.4, Criteria=0.7 Next question targets Constraints (lowest at 0.4): "You mentioned this should 'work on mobile'. Does that mean a native app, a responsive web app, or a PWA? And are there specific devices or OS versions you need to support?" ``` Why good: Identifies weakest dimension, asks specific question to improve it, doesn't batch multiple topics. Gathering codebase facts before asking: ``` [spawns explore agent: "find authentication implementation"] [receives: "Auth is in src/auth/ using JWT with passport.js"]

Question: "I see your project uses JWT authentication with passport.js in src/auth/. For this new feature, should we extend the existing auth middleware or create a separate authentication flow?"

Why good: Explored first, then asked an informed question. Never asks the user what the code already reveals.
</Good>

<Good>
Contrarian mode activation:

Round 5 | Contrarian Mode | Ambiguity: 42%

You've said this needs to support 10,000 concurrent users. What if it only needed to handle 100? Would the architecture change fundamentally, or is the 10K number an assumption rather than a measured requirement?

Why good: Challenges a specific assumption (scale requirement) that could dramatically simplify the solution.
</Good>

<Good>
Early exit with warning:

User: "That's enough, just build it" System: "Current ambiguity is 35% (threshold: 20%). Areas still unclear:

• Success Criteria: 0.5 (How do we verify the search ranking algorithm works correctly?)
• Constraints: 0.6 (No performance targets defined yet)

Proceeding may require rework. Continue anyway?" [Yes, proceed] [Ask 2-3 more questions] [Cancel]

Why good: Respects user's desire to stop but transparently shows the risk.
</Good>

<Bad>
Batching multiple questions:

"What's the target audience? And what tech stack? And how should auth work? Also, what's the deployment target?"

Why bad: Four questions at once — causes shallow answers and makes scoring inaccurate.
</Bad>

<Bad>
Asking about codebase facts:

"What database does your project use?"

Why bad: Should have spawned explore agent to find this. Never ask the user what the code already tells you.
</Bad>

<Bad>
Proceeding despite high ambiguity:

"Ambiguity is at 45% but we've done 5 rounds, so let's start building."

Why bad: 45% ambiguity means nearly half the requirements are unclear. The mathematical gate exists to prevent exactly this.
</Bad>
</Examples>

<Escalation_And_Stop_Conditions>
- **Hard cap at 20 rounds**: Proceed with whatever clarity exists, noting the risk
- **Soft warning at 10 rounds**: Offer to continue or proceed
- **Early exit (round 3+)**: Allow with warning if ambiguity > threshold
- **User says "stop", "cancel", "abort"**: Stop immediately, save state for resume
- **Ambiguity stalls** (same score +-0.05 for 3 rounds): Activate Ontologist mode to reframe
- **All dimensions at 0.9+**: Skip to spec generation even if not at round minimum
- **Codebase exploration fails**: Proceed as greenfield, note the limitation
</Escalation_And_Stop_Conditions>

<Final_Checklist>
- [ ] Interview completed (ambiguity ≤ threshold OR user chose early exit)
- [ ] Ambiguity score displayed after every round
- [ ] Challenge agents activated at correct thresholds (round 4, 6, 8)
- [ ] Spec file written to `.omc/specs/deep-interview-{slug}.md`
- [ ] Spec includes: goal, constraints, acceptance criteria, clarity breakdown, transcript
- [ ] Execution bridge presented via AskUserQuestion
- [ ] Selected execution mode invoked via Skill() (never direct implementation)
- [ ] If 3-stage pipeline selected: omc-plan --consensus --direct invoked, then autopilot with consensus plan
- [ ] State cleaned up after execution handoff
</Final_Checklist>

<Advanced>
## Configuration

Optional settings in `.claude/settings.json`:

```json
{
  "omc": {
    "deepInterview": {
      "ambiguityThreshold": 0.2,
      "maxRounds": 20,
      "softWarningRounds": 10,
      "minRoundsBeforeExit": 3,
      "enableChallengeAgents": true,
      "autoExecuteOnComplete": false,
      "defaultExecutionMode": "autopilot",
      "scoringModel": "opus"
    }
  }
}

Resume

If interrupted, run /deep-interview again. The skill reads state from .omc/state/deep-interview-state.json and resumes from the last completed round.

Integration with Autopilot

When autopilot receives a vague input (no file paths, function names, or concrete anchors), it can redirect to deep-interview:

User: "autopilot build me a thing"
Autopilot: "Your request is quite open-ended. Would you like to run a deep interview first to clarify requirements?"
  [Yes, interview first] [No, expand directly]

If the user chooses interview, autopilot invokes /deep-interview. When the interview completes and the user selects "Execute with autopilot", the spec becomes Phase 0 output and autopilot continues from Phase 1 (Planning).

The 3-Stage Pipeline: deep-interview → ralplan → autopilot

The recommended execution path chains three quality gates:

/deep-interview "vague idea"
  → Socratic Q&A until ambiguity ≤ 20%
  → Spec written to .omc/specs/deep-interview-{slug}.md
  → User selects "Ralplan → Autopilot"
  → /omc-plan --consensus --direct (spec as input, skip interview)
    → Planner creates implementation plan from spec
    → Architect reviews for architectural soundness
    → Critic validates quality and testability
    → Loop until consensus (max 5 iterations)
    → Consensus plan written to .omc/plans/
  → /autopilot (plan as input, skip Phase 0+1)
    → Phase 2: Parallel execution via Ralph + Ultrawork
    → Phase 3: QA cycling until tests pass
    → Phase 4: Multi-perspective validation
    → Phase 5: Cleanup

The omc-plan skill receives the spec with --consensus --direct flags because the deep interview already did the requirements gathering. The --direct flag (supported by the omc-plan skill, which ralplan aliases) skips the interview phase and goes straight to Planner → Architect → Critic consensus. The consensus plan includes:

• RALPLAN-DR summary (Principles, Decision Drivers, Options)
• ADR (Decision, Drivers, Alternatives, Why chosen, Consequences)
• Testable acceptance criteria (inherited from deep-interview spec)
• Implementation steps with file references

Autopilot receives the ralplan consensus plan and skips both Phase 0 (Expansion) and Phase 1 (Planning) since ralplan already produced a Critic-approved plan. Autopilot starts directly at Phase 2 (Execution).

Integration with Ralplan Gate

The ralplan pre-execution gate already redirects vague prompts to planning. Deep interview can serve as an alternative redirect target for prompts that are too vague even for ralplan:

Vague prompt → ralplan gate → deep-interview (if extremely vague) → ralplan (with clear spec) → autopilot

Brownfield vs Greenfield Weights

Dimension	Greenfield	Brownfield
Goal Clarity	40%	35%
Constraint Clarity	30%	25%
Success Criteria	30%	25%
Context Clarity	N/A	15%

Brownfield adds Context Clarity because modifying existing code safely requires understanding the system being changed.

Challenge Agent Modes

Mode	Activates	Purpose	Prompt Injection
Contrarian	Round 4+	Challenge assumptions	"What if the opposite were true?"
Simplifier	Round 6+	Remove complexity	"What's the simplest version?"
Ontologist	Round 8+ (if ambiguity > 0.3)	Find essence	"What IS this, really?"

Each mode is used exactly once, then normal Socratic questioning resumes. Modes are tracked in state to prevent repetition.

Ambiguity Score Interpretation

Score Range	Meaning	Action
0.0 - 0.1	Crystal clear	Proceed immediately
0.1 - 0.2	Clear enough	Proceed (default threshold)
0.2 - 0.4	Some gaps	Continue interviewing
0.4 - 0.6	Significant gaps	Focus on weakest dimensions
0.6 - 0.8	Very unclear	May need reframing (Ontologist)
0.8 - 1.0	Almost nothing known	Early stages, keep going

Task: {{ARGUMENTS}}