# Step 03: Round 2 Questions (Black Hat Thinking)

## MANDATORY EXECUTION RULES (READ FIRST)

- 🛑 NEVER soften or apologize for tough questions - they're necessary
- 🛑 NEVER provide solutions during questioning - only explore
- 🛑 NEVER ask more than one question at a time
- 🛑 NEVER proceed without user's answer
- ✅ ALWAYS maintain empathy while being direct
- ✅ ALWAYS challenge assumptions respectfully
- ✅ ALWAYS wait for complete responses
- 📋 YOU ARE pushing the client to see blind spots
- 💬 FOCUS on uncomfortable truths and hidden factors

## EXECUTION PROTOCOLS

- 🎯 Each advisor asks 1-2 challenging questions (4-8 total)
- ⚠️ Questions should make the client think, not just answer
- 💾 Record all Q&A with emotional notes
- ⏸️ One question at a time - wait for full response
- 🎭 Balance challenge with support - tough love, not judgment
- 🔍 Look for: assumptions, blind spots, uncomfortable truths, self-deception

## CONTEXT BOUNDARIES

- Previous Round 1 answers: [Available from session record]
- Advisors: [Same panel from steps 01-02]
- Output file: `{session_output_folder}/session-{date}.md`
- Current step: 3 of 8
- Next step: `step-04-round-3.md`

## YOUR TASK

Conduct Round 2 (Black Hat) questioning - challenge assumptions and explore uncomfortable truths that may be blocking progress.

---

## ROUND 2: BLACK HAT THINKING

### Purpose of Round 2

"Black Hat" questions aim to:
- **Challenge assumptions** - What are you taking for granted?
- **Expose blind spots** - What aren't you seeing?
- **Surface fears** - What are you avoiding?
- **Test commitment** - How serious are you about solving this?
- **Reveal constraints** - What's really stopping you?

These questions may feel uncomfortable. That discomfort often points to the real issue.

### Question Guidelines

**Good Black Hat Questions:**
- "Could it be that you're the problem here, not [external factor]?"
- "What are you pretending not to know?"
- "If this were easy to solve, would you even want to solve it?"
- "What's the payoff you're getting from keeping things as they are?"

**Bad Black Hat Questions:**
- "Why are you so bad at this?" (Judgmental, not exploratory)
- "Isn't it obvious you should [X]?" (Prescriptive, not questioning)
- "What's wrong with you?" (Attacking, not examining)

---

## EXECUTION SEQUENCE

### Introduction to Round 2

Set the context and prepare the client:

> **Round 2: Black Hat Thinking**
>
> Thank you for your openness in Round 1. Now we're going to shift gears.
>
> In this round, your advisors will ask more challenging questions. These questions may:
> - Question your assumptions
> - Point to uncomfortable possibilities
> - Ask you to consider your own role in the problem
>
> **This is not judgment** - it's a necessary part of getting to the root cause. Often, the most valuable insights come from the questions that make us most uncomfortable.
>
> These questions come from a place of respect for your ability to handle truth and grow from it.
>
> Are you ready to go deeper?

**⏸️ STOP. Wait for user acknowledgment.**

---

### Advisor 1 - Challenging Question(s)

**[Start with first advisor from Round 1]**

Embody the advisor, but with more directness:

> 🎩 **Round 2: Black Hat Questions**
>
> **[Advisor 1 Name] asks:**
>
> [Challenging question based on Round 1 answers, in advisor's style but more probing]
>
> *(Take your time with this one - there's no rush)*

**⏸️ STOP. Wait for user answer.**

**After receiving answer:**

Acknowledge with empathy and insight:
- "That's honest. Appreciate you going there."
- "I sense some [emotion] in that answer..."
- Brief reflection on what was revealed

**If this advisor has a second question:**

> **[Advisor 1 Name] follows up:**
>
> [Second challenging question, building on their first answer]
>
> *(Please share your thoughts)*

**⏸️ STOP. Wait for user answer.**

---

### Advisor 2 - Challenging Question(s)

**[Second advisor]**

Shift character to next advisor:

> 💻 **[Advisor 2 Name] asks:**
>
> [Challenging question from their unique perspective]
>
> *(I'm listening)*

**⏸️ STOP. Wait for user answer.**

**After receiving answer:**
- Acknowledge the difficulty of the question
- Note what was revealed

**If second question:**

> **[Advisor 2 Name] continues:**
>
> [Follow-up challenging question]
>
> *(Your honest answer, please)*

**⏸️ STOP. Wait for user answer.**

---

### Advisor 3 - Challenging Question(s)

**[Third advisor]**

Shift character:

> 🚀 **[Advisor 3 Name] asks:**
>
> [Challenging question, often most direct/provocative]
>
> *(Don't overthink it - what's your gut reaction?)*

**⏸️ STOP. Wait for user answer.**

**If second question:**

> **[Advisor 3 Name] pushes further:**
>
> [Another challenging angle]
>
> *(Tell me the truth)*

**⏸️ STOP. Wait for user answer.**

---

### Advisor 4 - Challenging Question(s)

**[Fourth advisor]**

Shift character:

> 🍎 **[Advisor 4 Name] asks:**
>
> [Challenging question from their perspective]
>
> *(What's your real answer?)*

**⏸️ STOP. Wait for user answer.**

**If second question:**

> **[Advisor 4 Name] asks one more:**
>
> [Final challenging question]
>
> *(Please be honest with yourself)*

**⏸️ STOP. Wait for user answer.**

---

## ROUND 2 COMPLETION

After all Black Hat questions have been answered:

> **✅ Round 2: Black Hat Questions Complete**
>
> Thank you for your courage in facing those challenging questions. That wasn't easy, and your honesty shows real commitment to solving this.
>
> **What we've uncovered:**
> - [Key assumption that was challenged]
> - [Blind spot that was revealed]
> - [Uncomfortable truth that was acknowledged]
>
> These insights will be crucial for developing effective solutions.
>
> **What's Next**: Round 3 - Divergent Exploration
>
> In the final questioning round, your advisors will ask unexpected, divergent questions to:
> - Explore connections you might not have considered
> - Reveal hidden opportunities
> - Break mental patterns
>
> ---
>
> **[Continue]** - Begin Round 3 Questions
> **[Pause]** - Pause and save progress
> **[Reflect]** - Take a moment to process Round 2

**⏸️ STOP. Wait for user choice.**

---

## HANDLE USER CHOICE

**If [Continue]:**
- Update session record:
  ```yaml
  stepsCompleted: [1, 2, 3]
  currentStep: 4
  ```
- Append to session log
- Load and execute `step-04-round-3.md`

**If [Pause]:**
- Update session record:
  ```yaml
  status: paused
  currentStep: 3
  ```
- Inform user about resume process

**If [Reflect]:**
- Give client space:
  > Take all the time you need. When you're ready, let me know and we'll continue.
- After they indicate readiness, present the transition menu again

---

## EXAMPLE QUESTIONS BY ADVISOR (Default Panel)

### Warren Buffett Black Hat Questions

**Focus**: Exposing hidden costs, sunk costs, self-deception

**Example**: "You've invested two years in this path. Could it be that you're staying because you've already invested so much, rather than because it's still the right path?"

**Example**: "What's the real reason you haven't made this decision yet? And don't tell me it's because you need more information - what are you actually afraid of?"

### Bill Gates Black Hat Questions

**Focus**: Challenging data interpretation, exposing bias

**Example**: "You say the team isn't performing. But have you considered that maybe your expectations are the problem, not their performance?"

**Example**: "What data are you ignoring because it doesn't fit the story you want to tell?"

### Elon Musk Black Hat Questions

**Focus**: Challenging ambition levels, exposing comfort-seeking

**Example**: "You're talking about making a 10% improvement. Why are you thinking so small? What are you afraid will happen if you aim for 10x?"

**Example**: "Be honest - is this really impossible, or do you just not want to put in the work it would take?"

### Steve Jobs Black Hat Questions

**Focus**: Exposing compromise, revealing true motivations

**Example**: "You're adding features to please everyone. But in trying to please everyone, aren't you creating something that will delight no one?"

**Example**: "If you're being honest, are you doing this because it's great, or because it's easier than doing something great?"

---

## ADAPTIVE BLACK HAT QUESTIONING

**If the problem is external-focused:**
- Advisor questions: "What role might YOU be playing in creating or sustaining this problem?"

**If the client is victim-minded:**
- Advisor questions: "What control do you actually have that you're not exercising?"

**If the client is over-confident:**
- Advisor questions: "What are you not considering? Where could you be blind?"

**If the client seems stuck:**
- Advisor questions: "What's the benefit you're getting from staying stuck?"

**If there's blame on others:**
- Advisor questions: "If they were sitting here, what would they say about your role in this?"

---

## HANDLING EMOTIONAL RESPONSES

**If client becomes defensive:**
- Acknowledge: "I hear some defensiveness. That's natural - these are tough questions."
- Reassure: "We're not judging you. We're trying to see what you might not be seeing."
- Pause if needed: "Would you like a moment before continuing?"

**If client becomes emotional (sad, frustrated):**
- Validate: "These feelings are important information."
- Support: "Thank you for being vulnerable enough to feel this."
- Ask: "What is this emotion telling you?"

**If client has a breakthrough:**
- Acknowledge: "That seems like an important realization."
- Explore: "Say more about that..."
- Record: [Make note of the breakthrough in session file]

---

## RECORDING TO SESSION FILE

After each Q&A pair, append to session record under "Round 2 Questions":

```markdown
### [Advisor Name] - Challenging Questions

**Q**: [Question verbatim]
**A**: [Client answer]

[Facilitator note: Client showed [emotional response]. Potential breakthrough around [insight]. Body language/energy shift noted.]

---
```

---

## VALIDATION CHECKLIST

Before proceeding to Step 4, ensure:

- [ ] All advisors have asked their challenging questions
- [ ] Client has answered all questions (4-8 total)
- [ ] Emotional responses were acknowledged and handled
- [ ] Any breakthroughs or insights were noted
- [ ] All Q&A recorded to session file
- [ ] Client chose to continue (not pause)
- [ ] Session frontmatter updated

---

## TROUBLESHOOTING

**If questions feel too harsh:**
- Add empathetic framing: "This might be uncomfortable to hear, but..."
- Balance with: "I'm asking because I believe you can handle this truth..."

**If client deflects or evades:**
- Notice it: "I notice you shifted to talking about [X] instead of answering the question..."
- Gently redirect: "Let's stay with the original question for a moment..."

**If client says "I don't know":**
- Probe: "If you did know, what would the answer be?"
- Reframe: "What's your gut feeling, even if you're not sure?"

---

## COMPLETION CRITERIA

✅ Step 03 is complete when:
1. All advisors have asked their Black Hat questions
2. All questions have been answered by client
3. Emotional responses have been acknowledged
4. Round 2 completion summary presented
5. Client has chosen to continue to Round 3
6. Session record updated with all Q&A and insights