542 lines
15 KiB
Markdown
542 lines
15 KiB
Markdown
# Discussion Framework & Documentation Best Practices
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**Date Created:** October 19, 2025
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**Purpose:** Guide for conducting productive strategic sessions with @men
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**Status:** Living document - refine based on experience
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**Based on:** Successful first session (Oct 19, 2025)
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---
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## Why This Framework Exists
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**The problem without structure:**
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- Strategic discussions become rambling, unfocused
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- Decisions made but not recorded → forgotten or disputed later
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- No clear action items → nothing gets done
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- Lessons learned evaporate → repeat same mistakes
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**The solution:**
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Structured approach to discussions + rigorous documentation = compounding knowledge and faster execution
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---
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## Types of Strategic Discussions
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### 1. Onboarding / Context-Setting Sessions
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**When:** First meeting, major project pivot, new stakeholder joins
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**Duration:** 2-3 hours
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**Goal:** Shared understanding of situation, constraints, goals
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**Output:** Comprehensive context documents (market, reality check, etc.)
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**Example:** October 19, 2025 session (our first)
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---
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### 2. Decision-Making Sessions
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**When:** Major crossroads, must choose between options
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**Duration:** 1-2 hours
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**Goal:** Make a specific decision with clear rationale
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**Output:** Decision document with options analyzed, choice made, next steps
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**Example topics:**
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- ICP selection (upcoming)
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- Pricing model finalization
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- Launch timing decision
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- Pivot vs. continue assessment
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---
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### 3. Problem-Solving Sessions
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**When:** Stuck on specific challenge, need breakthrough
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**Duration:** 30-60 minutes
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**Goal:** Identify root cause, generate solutions, pick path forward
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**Output:** Problem analysis + solution plan
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**Example topics:**
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- Customer churn spike
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- Marketing channel not working
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- Technical blocker
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- Founder burnout warning signs
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---
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### 4. Review & Planning Sessions
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**When:** Regular cadence (weekly, monthly, quarterly)
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**Duration:** 30 min (weekly), 1 hour (monthly), 2-3 hours (quarterly)
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**Goal:** Assess progress, adjust course, plan next period
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**Output:** Progress report + updated action items
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**Structure:**
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- **Weekly:** Metrics review, blockers, priorities for next week
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- **Monthly:** MRR/churn/customer count, goal progress, monthly OKRs
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- **Quarterly:** Big decisions (pivot/continue/stop), strategy refresh, quarterly goals
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---
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### 5. Learning Sessions
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**When:** After major event (launch, big failure, unexpected success)
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**Duration:** 30-60 minutes
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**Goal:** Extract lessons, update mental models, prevent repeat mistakes
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**Output:** Lessons learned document
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**Example topics:**
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- Post-launch retrospective
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- Why X campaign failed
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- Why Y customer churned
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- Unexpected growth spike - what worked?
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---
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## Session Structure Template
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### Pre-Session (5-10 min)
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**Oleg prepares:**
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1. **Topic definition:** What specific question/decision are we addressing?
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2. **Context sharing:** Links to relevant docs, data, previous discussions
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3. **Desired outcome:** What does success look like for this session?
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**Example:**
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```
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Topic: ICP Selection Decision
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Context: Completed self-assessment (see 03-icp-research-questions.md, Part 1)
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Desired outcome: Select ONE ICP to validate, understand why, know next steps
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```
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---
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### Opening (5 min)
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**@men confirms:**
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- Is the topic clear?
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- Do I have all necessary context?
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- What's the time limit?
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- Any constraints/considerations to keep in mind?
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**Set ground rules:**
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- Time box discussion (don't spiral)
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- Park tangential topics (add to backlog)
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- Challenge assumptions (truth over comfort)
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- Document as we go (don't rely on memory)
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---
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### Discussion Phase (30-90 min, depending on session type)
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**For Decision-Making Sessions:**
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1. **Frame the decision** (5 min)
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- What are we deciding?
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- Why now?
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- What happens if we don't decide?
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2. **Explore options** (20-30 min)
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- Brainstorm alternatives (no judgment yet)
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- For each option: pros, cons, risks, data needed
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- Identify information gaps
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3. **Analyze trade-offs** (15-20 min)
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- Which option best fits our constraints?
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- What's our unfair advantage for each?
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- Which has fastest feedback loop?
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- Which is reversible vs. irreversible?
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4. **Make decision** (10 min)
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- Choose one option
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- Articulate WHY (rationale matters for future reference)
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- Define success criteria
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- Set review date
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**For Problem-Solving Sessions:**
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1. **Define problem precisely** (10 min)
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- What's the symptom vs. root cause?
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- Quantify impact (revenue, time, customers)
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- When did it start?
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2. **Generate solutions** (15 min)
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- Brainstorm (quantity over quality)
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- Evaluate feasibility
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- Estimate effort/impact for each
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3. **Pick solution + plan** (10 min)
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- Choose highest impact/effort ratio
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- Break into concrete steps
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- Assign timeline
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**For Review Sessions:**
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1. **Metrics review** (10 min)
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- MRR, customers, churn, usage
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- Compare to goals
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- Trend analysis (growing/flat/declining)
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2. **Qualitative assessment** (10 min)
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- Customer feedback themes
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- Energy/momentum level
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- Obstacles encountered
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3. **Adjust course** (10 min)
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- What to keep doing?
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- What to stop?
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- What to start?
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- Next period priorities
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---
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### Closing (5-10 min)
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**Summarize:**
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- What did we decide/learn?
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- Why did we decide this?
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- What are the next steps?
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- Who owns what?
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- When do we review?
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**Parking lot review:**
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- Topics raised but not discussed
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- Add to future topics backlog
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- Prioritize for next sessions
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---
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### Post-Session (15-30 min)
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**Documentation (CRITICAL):**
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@men creates/updates relevant documents:
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- Decision logs
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- Action items
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- Context for future reference
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**Oleg responsibilities:**
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- Execute action items
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- Flag blockers immediately (don't wait)
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- Update docs if situation changes
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---
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## Documentation Standards
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### Every Document Must Include
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**Header section:**
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```markdown
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# Document Title
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**Date:** [Creation date]
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**Purpose:** [Why this doc exists]
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**Status:** [Draft / Working / Final / Deprecated]
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**Related docs:** [Links to connected documents]
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```
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**Core content:**
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- Clear structure (headers, bullet points, tables)
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- Specific, actionable information (no vague statements)
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- Context (why are we documenting this?)
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- Decisions explicitly marked (✅ Decided, ⳠPending, 🔮 Future)
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**Footer section:**
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```markdown
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**Document owner:** [Who maintains this]
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**Next review:** [When to revisit]
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**Last updated:** [Date of last edit]
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```
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---
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### Decision Documentation Template
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For every major decision, create a record:
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```markdown
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## Decision: [Title]
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**Date:** [When decided]
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**Context:** [Why this decision was needed]
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**Options considered:**
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1. Option A: [Pros / Cons / Estimated outcome]
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2. Option B: [Pros / Cons / Estimated outcome]
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3. Option C: [Pros / Cons / Estimated outcome]
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**Decision made:** [Which option chosen]
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**Rationale:** [WHY we chose this - this is most important part]
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**Success criteria:** [How we'll know if this was right]
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**Review date:** [When we'll reassess]
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**Reversibility:** [Can we undo this easily? Y/N]
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**Owner:** [Who executes]
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**Next steps:** [Immediate actions]
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```
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**Why this matters:**
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- Prevents relitigating decisions
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- Provides context for future pivots
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- Shows thinking process for learning
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---
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### Action Items Format
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Every action item must have:
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- [ ] **Clear task** (specific, not vague)
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- **Owner:** [Who is responsible]
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- **Deadline:** [When it's due]
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- **Success criteria:** [What "done" looks like]
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- **Blocker flag:** [Any dependencies or obstacles]
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**Example:**
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```markdown
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- [ ] Conduct 10 customer interviews with web dev agencies
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- **Owner:** Oleg
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- **Deadline:** Nov 5, 2025
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- **Success:** 10 interviews completed, notes documented using template
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- **Blocker:** Need to identify where these agencies hang out (Reddit? Slack?)
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```
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**Review cadence:**
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- Daily: Oleg checks his action items
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- Weekly: Review progress in check-in session
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- Monthly: Clear completed, escalate blocked
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---
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## Communication Best Practices
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### What Makes Good Questions
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**⌠Bad questions:**
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- "What do you think about this idea?" (too vague)
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- "Is this a good market?" (no context)
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- "Should I do X?" (lacks your analysis)
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**✅ Good questions:**
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- "I think X is true because Y. Do you see flaws in my reasoning?"
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- "I've narrowed to 2 options: A vs. B. Here's my analysis [details]. Which would you prioritize and why?"
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- "Here's the data [specifics]. I'm interpreting it as Z. Do you read it differently?"
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**Key principles:**
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- Share your thinking FIRST
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- Provide context and data
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- Ask for critique, not validation
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- Specific > general
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---
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### How to Disagree Productively
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**When you (Oleg) disagree with @men:**
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1. Say so explicitly: "I'm not convinced because..."
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2. Explain your reasoning (don't just reject)
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3. Ask for evidence: "What data supports this?"
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4. Propose alternative: "What if we tried Y instead?"
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**When @men challenges you:**
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1. Don't defend reflexively (listen first)
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2. Ask clarifying questions
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3. Take time to think (don't need instant response)
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4. Update your mental model if evidence is strong
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**Disagreement is GOOD** - it surfaces blind spots and leads to better decisions.
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---
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### When to Escalate Discussions
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**Bring to @men immediately (don't wait for scheduled check-in):**
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- Major pivot consideration (PMF not happening)
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- Unexpected crisis (employer found out, health issue, etc.)
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- Big opportunity (viral moment, major customer interest)
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- Existential doubt ("Should I even continue?")
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**Can wait for next session:**
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- Feature prioritization questions
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- Minor tactical decisions
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- Routine progress updates
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- General brainstorming
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**Use async updates for:**
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- Weekly metrics (MRR, customers, churn)
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- Completed action items
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- New learnings from customer conversations
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---
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## Meeting Hygiene Rules
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### Time Management
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- **Start on time** (respect both calendars)
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- **Time box discussions** (set timer if needed)
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- **End on time** (or explicitly extend with agreement)
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- **Park tangents** (note for future, don't chase now)
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### Energy Management
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- **No meetings when exhausted** (reschedule if needed)
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- **No meetings after 10 PM** (Oleg's boundary for family/sleep)
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- **Take breaks** (if >90 min session, 5-10 min break)
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### Focus Management
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- **Single topic per session** (exceptions: quick check-ins)
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- **No multitasking** (close email, Slack, etc.)
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- **Phones away** (full presence required)
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- **Take notes live** (capture key points as discussed)
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---
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## Documentation Workflow
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### Oleg's Responsibilities
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1. **Before session:**
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- Prepare context (data, previous docs, questions)
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- Define desired outcome
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- Share with @men
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2. **During session:**
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- Take rough notes (key points, decisions)
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- Flag items for documentation
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- Confirm action items
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3. **After session:**
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- Review created documents for accuracy
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- Execute action items
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- Update docs if situation changes
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- Share progress in next check-in
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---
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### @men's Responsibilities
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1. **Before session:**
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- Review shared context
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- Research if needed (market data, case studies)
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- Prepare frameworks/questions
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2. **During session:**
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- Guide discussion structure
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- Challenge assumptions with evidence
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- Synthesize insights
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- Drive to decisions
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3. **After session:**
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- Create structured documentation
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- Formalize decisions and rationale
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- Update related documents
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- Set up next steps
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---
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## Quality Checks
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### Before Ending Any Session, Verify:
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- [ ] Clear decision made (or explicit non-decision with next steps)
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- [ ] Rationale documented (why we chose this)
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- [ ] Action items defined (who, what, when)
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- [ ] Success criteria set (how to measure outcome)
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- [ ] Review date scheduled (when to reassess)
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- [ ] Related docs updated (or new docs created)
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### Monthly Documentation Audit:
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- [ ] Are all pending decisions still relevant?
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- [ ] Are action items getting completed on time?
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- [ ] Are old documents deprecated/archived?
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- [ ] Are new patterns emerging (update frameworks)?
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---
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## Red Flags (Session Not Working)
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**Warning signs:**
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- Circular discussions (keep returning to same point)
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- Analysis paralysis (can't decide despite enough data)
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- Defensive reactions (rejecting feedback without reason)
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- Vague outcomes ("we should think about this more")
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- No documentation created (relying on memory)
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**How to reset:**
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1. **Stop the session** (don't push through)
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2. **Name the problem** ("We're going in circles")
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3. **Identify blocker** (Missing data? Unclear goal? Emotional resistance?)
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4. **Adjust approach** (Get data? Clarify goal? Take break?)
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5. **Reschedule if needed** (Better to pause than waste time)
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---
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## Success Patterns (Session Going Well)
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**Green lights:**
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- Decisions made with confidence
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- Clear action items emerging naturally
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- "Aha moments" happening
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- Energy is UP (not drained)
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- Documentation feels valuable (not bureaucratic)
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- Disagreements resolved with data/logic
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- Next steps are obvious
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**Reinforce what works:**
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- Note which frameworks were useful
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- Repeat successful session structures
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- Build on previous decisions (don't relitigate)
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---
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## Evolution & Learning
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### This Framework is NOT Static
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**Update when:**
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- Better approach discovered
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- Pattern repeated across sessions (formalize it)
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- Something consistently doesn't work (remove it)
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- New session type needed (add template)
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**How to update:**
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1. Note the need (during or after session)
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2. Discuss with @men
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3. Revise framework document
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4. Date the change (track evolution)
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**Version control:**
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Include at top of document:
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```markdown
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**Version:** 1.0
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**Last updated:** Oct 19, 2025
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**Change log:**
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- v1.0 (Oct 19, 2025): Initial framework based on first session
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```
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---
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## Appendix: Quick Reference
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### Session Prep Checklist
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- [ ] Topic defined
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- [ ] Context docs shared
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- [ ] Desired outcome clear
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- [ ] Time allocated
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- [ ] Any constraints noted
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### Session Execution Checklist
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- [ ] Opening: Confirm topic, time, context
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- [ ] Discussion: Follow appropriate structure
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- [ ] Closing: Summarize, next steps, parking lot
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- [ ] Documentation: Create/update docs
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### Post-Session Checklist
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- [ ] Docs created and shared
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- [ ] Action items clear (who, what, when)
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- [ ] Next review scheduled
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- [ ] Related docs updated
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---
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## Template Library
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**Quick access to common templates:**
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1. Decision documentation (see above)
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2. Action item format (see above)
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3. Problem-solving canvas (in dedicated template file)
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4. Customer interview script (see `03-icp-research-questions.md`)
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5. Weekly check-in format (in dedicated template file)
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6. Monthly review structure (in dedicated template file)
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**Note:** Full templates to be created as needed and linked here.
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---
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**Document owner:** @men (framework design) + Oleg (adherence)
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**Version:** 1.0
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**Last updated:** October 19, 2025
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**Next review:** After 5 sessions (to assess what's working)
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**Status:** Living document - will evolve with experience
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