# Discussion Framework & Documentation Best Practices

**Date Created:** October 19, 2025
**Purpose:** Guide for conducting productive strategic sessions with @men
**Status:** Living document - refine based on experience
**Based on:** Successful first session (Oct 19, 2025)

---

## Why This Framework Exists

**The problem without structure:**
- Strategic discussions become rambling, unfocused
- Decisions made but not recorded → forgotten or disputed later
- No clear action items → nothing gets done
- Lessons learned evaporate → repeat same mistakes

**The solution:**
Structured approach to discussions + rigorous documentation = compounding knowledge and faster execution

---

## Types of Strategic Discussions

### 1. Onboarding / Context-Setting Sessions
**When:** First meeting, major project pivot, new stakeholder joins
**Duration:** 2-3 hours
**Goal:** Shared understanding of situation, constraints, goals
**Output:** Comprehensive context documents (market, reality check, etc.)

**Example:** October 19, 2025 session (our first)

---

### 2. Decision-Making Sessions
**When:** Major crossroads, must choose between options
**Duration:** 1-2 hours
**Goal:** Make a specific decision with clear rationale
**Output:** Decision document with options analyzed, choice made, next steps

**Example topics:**
- ICP selection (upcoming)
- Pricing model finalization
- Launch timing decision
- Pivot vs. continue assessment

---

### 3. Problem-Solving Sessions
**When:** Stuck on specific challenge, need breakthrough
**Duration:** 30-60 minutes
**Goal:** Identify root cause, generate solutions, pick path forward
**Output:** Problem analysis + solution plan

**Example topics:**
- Customer churn spike
- Marketing channel not working
- Technical blocker
- Founder burnout warning signs

---

### 4. Review & Planning Sessions
**When:** Regular cadence (weekly, monthly, quarterly)
**Duration:** 30 min (weekly), 1 hour (monthly), 2-3 hours (quarterly)
**Goal:** Assess progress, adjust course, plan next period
**Output:** Progress report + updated action items

**Structure:**
- **Weekly:** Metrics review, blockers, priorities for next week
- **Monthly:** MRR/churn/customer count, goal progress, monthly OKRs
- **Quarterly:** Big decisions (pivot/continue/stop), strategy refresh, quarterly goals

---

### 5. Learning Sessions
**When:** After major event (launch, big failure, unexpected success)
**Duration:** 30-60 minutes
**Goal:** Extract lessons, update mental models, prevent repeat mistakes
**Output:** Lessons learned document

**Example topics:**
- Post-launch retrospective
- Why X campaign failed
- Why Y customer churned
- Unexpected growth spike - what worked?

---

## Session Structure Template

### Pre-Session (5-10 min)
**Oleg prepares:**
1. **Topic definition:** What specific question/decision are we addressing?
2. **Context sharing:** Links to relevant docs, data, previous discussions
3. **Desired outcome:** What does success look like for this session?

**Example:**
```
Topic: ICP Selection Decision
Context: Completed self-assessment (see 03-icp-research-questions.md, Part 1)
Desired outcome: Select ONE ICP to validate, understand why, know next steps
```

---

### Opening (5 min)
**@men confirms:**
- Is the topic clear?
- Do I have all necessary context?
- What's the time limit?
- Any constraints/considerations to keep in mind?

**Set ground rules:**
- Time box discussion (don't spiral)
- Park tangential topics (add to backlog)
- Challenge assumptions (truth over comfort)
- Document as we go (don't rely on memory)

---

### Discussion Phase (30-90 min, depending on session type)

**For Decision-Making Sessions:**
1. **Frame the decision** (5 min)
   - What are we deciding?
   - Why now?
   - What happens if we don't decide?

2. **Explore options** (20-30 min)
   - Brainstorm alternatives (no judgment yet)
   - For each option: pros, cons, risks, data needed
   - Identify information gaps

3. **Analyze trade-offs** (15-20 min)
   - Which option best fits our constraints?
   - What's our unfair advantage for each?
   - Which has fastest feedback loop?
   - Which is reversible vs. irreversible?

4. **Make decision** (10 min)
   - Choose one option
   - Articulate WHY (rationale matters for future reference)
   - Define success criteria
   - Set review date

**For Problem-Solving Sessions:**
1. **Define problem precisely** (10 min)
   - What's the symptom vs. root cause?
   - Quantify impact (revenue, time, customers)
   - When did it start?

2. **Generate solutions** (15 min)
   - Brainstorm (quantity over quality)
   - Evaluate feasibility
   - Estimate effort/impact for each

3. **Pick solution + plan** (10 min)
   - Choose highest impact/effort ratio
   - Break into concrete steps
   - Assign timeline

**For Review Sessions:**
1. **Metrics review** (10 min)
   - MRR, customers, churn, usage
   - Compare to goals
   - Trend analysis (growing/flat/declining)

2. **Qualitative assessment** (10 min)
   - Customer feedback themes
   - Energy/momentum level
   - Obstacles encountered

3. **Adjust course** (10 min)
   - What to keep doing?
   - What to stop?
   - What to start?
   - Next period priorities

---

### Closing (5-10 min)
**Summarize:**
- What did we decide/learn?
- Why did we decide this?
- What are the next steps?
- Who owns what?
- When do we review?

**Parking lot review:**
- Topics raised but not discussed
- Add to future topics backlog
- Prioritize for next sessions

---

### Post-Session (15-30 min)
**Documentation (CRITICAL):**
@men creates/updates relevant documents:
- Decision logs
- Action items
- Context for future reference

**Oleg responsibilities:**
- Execute action items
- Flag blockers immediately (don't wait)
- Update docs if situation changes

---

## Documentation Standards

### Every Document Must Include

**Header section:**
```markdown
# Document Title

**Date:** [Creation date]
**Purpose:** [Why this doc exists]
**Status:** [Draft / Working / Final / Deprecated]
**Related docs:** [Links to connected documents]
```

**Core content:**
- Clear structure (headers, bullet points, tables)
- Specific, actionable information (no vague statements)
- Context (why are we documenting this?)
- Decisions explicitly marked (✅ Decided, ⏳ Pending, 🔮 Future)

**Footer section:**
```markdown
**Document owner:** [Who maintains this]
**Next review:** [When to revisit]
**Last updated:** [Date of last edit]
```

---

### Decision Documentation Template

For every major decision, create a record:

```markdown
## Decision: [Title]
**Date:** [When decided]
**Context:** [Why this decision was needed]
**Options considered:**
1. Option A: [Pros / Cons / Estimated outcome]
2. Option B: [Pros / Cons / Estimated outcome]
3. Option C: [Pros / Cons / Estimated outcome]

**Decision made:** [Which option chosen]
**Rationale:** [WHY we chose this - this is most important part]
**Success criteria:** [How we'll know if this was right]
**Review date:** [When we'll reassess]
**Reversibility:** [Can we undo this easily? Y/N]

**Owner:** [Who executes]
**Next steps:** [Immediate actions]
```

**Why this matters:**
- Prevents relitigating decisions
- Provides context for future pivots
- Shows thinking process for learning

---

### Action Items Format

Every action item must have:
- [ ] **Clear task** (specific, not vague)
- **Owner:** [Who is responsible]
- **Deadline:** [When it's due]
- **Success criteria:** [What "done" looks like]
- **Blocker flag:** [Any dependencies or obstacles]

**Example:**
```markdown
- [ ] Conduct 10 customer interviews with web dev agencies
  - **Owner:** Oleg
  - **Deadline:** Nov 5, 2025
  - **Success:** 10 interviews completed, notes documented using template
  - **Blocker:** Need to identify where these agencies hang out (Reddit? Slack?)
```

**Review cadence:**
- Daily: Oleg checks his action items
- Weekly: Review progress in check-in session
- Monthly: Clear completed, escalate blocked

---

## Communication Best Practices

### What Makes Good Questions

**❌ Bad questions:**
- "What do you think about this idea?" (too vague)
- "Is this a good market?" (no context)
- "Should I do X?" (lacks your analysis)

**✅ Good questions:**
- "I think X is true because Y. Do you see flaws in my reasoning?"
- "I've narrowed to 2 options: A vs. B. Here's my analysis [details]. Which would you prioritize and why?"
- "Here's the data [specifics]. I'm interpreting it as Z. Do you read it differently?"

**Key principles:**
- Share your thinking FIRST
- Provide context and data
- Ask for critique, not validation
- Specific > general

---

### How to Disagree Productively

**When you (Oleg) disagree with @men:**
1. Say so explicitly: "I'm not convinced because..."
2. Explain your reasoning (don't just reject)
3. Ask for evidence: "What data supports this?"
4. Propose alternative: "What if we tried Y instead?"

**When @men challenges you:**
1. Don't defend reflexively (listen first)
2. Ask clarifying questions
3. Take time to think (don't need instant response)
4. Update your mental model if evidence is strong

**Disagreement is GOOD** - it surfaces blind spots and leads to better decisions.

---

### When to Escalate Discussions

**Bring to @men immediately (don't wait for scheduled check-in):**
- Major pivot consideration (PMF not happening)
- Unexpected crisis (employer found out, health issue, etc.)
- Big opportunity (viral moment, major customer interest)
- Existential doubt ("Should I even continue?")

**Can wait for next session:**
- Feature prioritization questions
- Minor tactical decisions
- Routine progress updates
- General brainstorming

**Use async updates for:**
- Weekly metrics (MRR, customers, churn)
- Completed action items
- New learnings from customer conversations

---

## Meeting Hygiene Rules

### Time Management
- **Start on time** (respect both calendars)
- **Time box discussions** (set timer if needed)
- **End on time** (or explicitly extend with agreement)
- **Park tangents** (note for future, don't chase now)

### Energy Management
- **No meetings when exhausted** (reschedule if needed)
- **No meetings after 10 PM** (Oleg's boundary for family/sleep)
- **Take breaks** (if >90 min session, 5-10 min break)

### Focus Management
- **Single topic per session** (exceptions: quick check-ins)
- **No multitasking** (close email, Slack, etc.)
- **Phones away** (full presence required)
- **Take notes live** (capture key points as discussed)

---

## Documentation Workflow

### Oleg's Responsibilities
1. **Before session:**
   - Prepare context (data, previous docs, questions)
   - Define desired outcome
   - Share with @men

2. **During session:**
   - Take rough notes (key points, decisions)
   - Flag items for documentation
   - Confirm action items

3. **After session:**
   - Review created documents for accuracy
   - Execute action items
   - Update docs if situation changes
   - Share progress in next check-in

---

### @men's Responsibilities
1. **Before session:**
   - Review shared context
   - Research if needed (market data, case studies)
   - Prepare frameworks/questions

2. **During session:**
   - Guide discussion structure
   - Challenge assumptions with evidence
   - Synthesize insights
   - Drive to decisions

3. **After session:**
   - Create structured documentation
   - Formalize decisions and rationale
   - Update related documents
   - Set up next steps

---

## Quality Checks

### Before Ending Any Session, Verify:
- [ ] Clear decision made (or explicit non-decision with next steps)
- [ ] Rationale documented (why we chose this)
- [ ] Action items defined (who, what, when)
- [ ] Success criteria set (how to measure outcome)
- [ ] Review date scheduled (when to reassess)
- [ ] Related docs updated (or new docs created)

### Monthly Documentation Audit:
- [ ] Are all pending decisions still relevant?
- [ ] Are action items getting completed on time?
- [ ] Are old documents deprecated/archived?
- [ ] Are new patterns emerging (update frameworks)?

---

## Red Flags (Session Not Working)

**Warning signs:**
- Circular discussions (keep returning to same point)
- Analysis paralysis (can't decide despite enough data)
- Defensive reactions (rejecting feedback without reason)
- Vague outcomes ("we should think about this more")
- No documentation created (relying on memory)

**How to reset:**
1. **Stop the session** (don't push through)
2. **Name the problem** ("We're going in circles")
3. **Identify blocker** (Missing data? Unclear goal? Emotional resistance?)
4. **Adjust approach** (Get data? Clarify goal? Take break?)
5. **Reschedule if needed** (Better to pause than waste time)

---

## Success Patterns (Session Going Well)

**Green lights:**
- Decisions made with confidence
- Clear action items emerging naturally
- "Aha moments" happening
- Energy is UP (not drained)
- Documentation feels valuable (not bureaucratic)
- Disagreements resolved with data/logic
- Next steps are obvious

**Reinforce what works:**
- Note which frameworks were useful
- Repeat successful session structures
- Build on previous decisions (don't relitigate)

---

## Evolution & Learning

### This Framework is NOT Static

**Update when:**
- Better approach discovered
- Pattern repeated across sessions (formalize it)
- Something consistently doesn't work (remove it)
- New session type needed (add template)

**How to update:**
1. Note the need (during or after session)
2. Discuss with @men
3. Revise framework document
4. Date the change (track evolution)

**Version control:**
Include at top of document:
```markdown
**Version:** 1.0
**Last updated:** Oct 19, 2025
**Change log:**
- v1.0 (Oct 19, 2025): Initial framework based on first session
```

---

## Appendix: Quick Reference

### Session Prep Checklist
- [ ] Topic defined
- [ ] Context docs shared
- [ ] Desired outcome clear
- [ ] Time allocated
- [ ] Any constraints noted

### Session Execution Checklist
- [ ] Opening: Confirm topic, time, context
- [ ] Discussion: Follow appropriate structure
- [ ] Closing: Summarize, next steps, parking lot
- [ ] Documentation: Create/update docs

### Post-Session Checklist
- [ ] Docs created and shared
- [ ] Action items clear (who, what, when)
- [ ] Next review scheduled
- [ ] Related docs updated

---

## Template Library

**Quick access to common templates:**
1. Decision documentation (see above)
2. Action item format (see above)
3. Problem-solving canvas (in dedicated template file)
4. Customer interview script (see `03-icp-research-questions.md`)
5. Weekly check-in format (in dedicated template file)
6. Monthly review structure (in dedicated template file)

**Note:** Full templates to be created as needed and linked here.

---

**Document owner:** @men (framework design) + Oleg (adherence)
**Version:** 1.0
**Last updated:** October 19, 2025
**Next review:** After 5 sessions (to assess what's working)
**Status:** Living document - will evolve with experience