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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:

# 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:

**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:

## 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:

- [ ] 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:

**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 execution/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