Facilitation Playbook: Running Each Phase Session

This playbook gives you a concrete plan for structuring each phase of a strategic planning engagement. It covers who should be in the room, how long each session typically takes, what the agenda looks like, and what to do when the team gets stuck.

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Engagement Overview

Typical Engagement Timeline

Week	Phase	Sessions	Key Output
1	Pre-work	Kickoff + org data entry	Organization context populated
2-3	LEARN	2-3 sessions (2 hours each)	5-7 key insights
3-4	FOCUS	1-2 sessions (2-3 hours each)	Competitive focus, winning proposition, max 5 priorities
4-5	ALIGN	1-2 sessions (2 hours each)	Gap statements for each priority
5-6	EXECUTE	1-2 sessions (2-3 hours each)	Leadership message, action plans, 30-day wins

Total: 6-10 sessions over 4-6 weeks. Compress for urgency (minimum 4 sessions over 2 weeks) or extend for thoroughness (up to 12 sessions over 8 weeks).

Who Should Attend

Role	LEARN	FOCUS	ALIGN	EXECUTE
CEO / General Manager	All sessions	All sessions	All sessions	All sessions
C-suite / SVPs	All sessions	All sessions	Relevant sessions	All sessions
Department heads	Relevant sessions	Optional	Their priority sessions	Their priority sessions
Subject matter experts	As needed	Optional	Optional	Optional
Board liaison	Optional (observer)	Final session	Optional	Final session

Ideal group size: 5-8 people for working sessions. Larger groups slow down strategic conversation. If you need broader input, gather it asynchronously and bring it into the session as data.

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Pre-Work: The Kickoff Session

Duration: 1.5 hours

Objectives

• Align on the purpose and process of the engagement
• Set expectations for participation and time commitment
• Assign data collection responsibilities
• Ensure platform access for all participants

Agenda

1. (15 min) Introduction and context — why this planning process, why now, what is different about this approach
2. (20 min) Framework overview — walk through LEARN, FOCUS, ALIGN, EXECUTE at a high level (use the Strategic Learning Framework guide as your reference)
3. (15 min) Platform walkthrough — demonstrate the planning chatbot, canvas, and execution dashboard
4. (20 min) Data collection assignments — assign who will populate each org context tab (competitors, customers, products, financials). Set a deadline of 48 hours before the first LEARN session.
5. (10 min) Logistics — session schedule, calendar invites, platform invitations
6. (10 min) Questions

Critical: The kickoff is where you establish that this process will be honest and uncomfortable. Say it directly: "I am going to push you to confront hard truths. Living Company AI is going to challenge your assumptions. This is by design. Comfortable strategy is bad strategy."

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Phase 1: LEARN Sessions

Duration: 2 hours per session, 2-3 sessions

Session 1: External Landscape

Focus: Broader Environment + Industry Dynamics

Agenda

1. (10 min) Context setting — review the situation analysis framework, explain the five areas
2. (35 min) Broader Environment deep dive — use Living Company AI toprobe economic, social, technological, demographic, regulatory trends. Ask: "What trends will reshape this industry in 3-5 years?"
3. (35 min) Industry Dynamics deep dive — probe value chain shifts, new entrants, success factors, margin pressure. Ask: "Where is profit migrating in this industry?"
4. (25 min) Insight capture — review what Living Company AIsurfaced. Challenge any vague insights. Push for specificity and scoring.
5. (15 min) Prep for next session — identify data gaps. Assign homework: "Talk to three customers before next session."

Session 2: Customers and Competitors

Focus: Customer Analysis + Competitive Landscape

Agenda

1. (10 min) Recap — review insights from Session 1, note any updates to org data
2. (35 min) Customer deep dive — explore needs, pain points, unmet needs, buying criteria by segment. Ask: "What do customers actually need vs. what we assume they need?"
3. (35 min) Competitor deep dive — analyze business models, strategic intent, recent moves, vulnerabilities. Ask: "If you were hired as CEO of your toughest competitor, how would you attack your company?"
4. (25 min) Pattern identification — look for convergences and contradictions across the data. Living Company AI will flag these proactively.
5. (15 min) Preview Own Realities — set up the honest self-assessment for Session 3.

Session 3: Own Realities and Insight Synthesis

Focus: Honest self-assessment + synthesize all LEARN insights

Agenda

1. (10 min) Recap — review customer and competitor insights
2. (30 min) Own Realities deep dive — performance trends, genuine strengths and weaknesses, cultural truths. This is the hardest conversation. Push hard: "What are the things you know but do not talk about?"
3. (30 min) Insight synthesis — review all captured insights. Score each one. Remove weak ones. Ask: "If we could only act on three of these insights, which three would change the game?"
4. (30 min) Assumption surfacing — review the assumptions Living Company AI has flagged. Identify the load-bearing ones. Propose tests.
5. (20 min) Transition to FOCUS — summarize the LEARN findings. Preview the choices that need to be made.

When the Team Gets Stuck in LEARN

Symptom	Intervention
Team stays at surface level ("the market is competitive")	Ask: "Compared to what? Be specific. Name the competitor and the specific advantage they have over you."
Team avoids Own Realities	Ask: "If I interviewed your top 10 customers anonymously, what would they say about working with you that you would not want to hear?"
Analysis paralysis — too much data, no synthesis	Ask: "Of everything we have discussed, what are the two truths that should scare you most?"
Team keeps circling back to solutions	Say: "We are not solving yet. We are understanding. Tell me what is really happening before we decide what to do about it."

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Phase 2: FOCUS Sessions

Duration: 2-3 hours per session, 1-2 sessions

Session Structure

Agenda

1. (15 min) LEARN recap — display the Canvas. Review the top insights. Remind the team: "These are the truths we agreed on. Now we make choices."
2. (30 min) Competitive Focus — which markets, which customers, which offerings. Equally important: which markets, customers, and offerings are we saying NO to? Use Living Company AI tostress-test each choice against the insights.
3. (30 min) Winning Proposition — what unique value do we offer? Test it: "If we replace our name with a competitor's name, is this still true?" If yes, it is not distinctive enough.
4. (45 min) Key Priorities — maximum 5. This is where the hardest conversations happen. Every priority must trace back to a LEARN insight. If the team proposes a sixth priority, force the trade-off: "Which of the current five is less important?"
5. (15 min) Assumption check — what assumptions underpin these choices? Are they tested?
6. (15 min) Transition to ALIGN — preview the gap analysis work ahead.

When the Team Gets Stuck in FOCUS

Symptom	Intervention
Refuses to choose ("we serve all segments")	Ask: "If you had to cut your budget by 40% tomorrow, which segments would you keep and which would you drop? That is your real focus."
Priority list keeps growing beyond 5	Say: "I need you to rank these by impact. Now draw a line after number 5. Everything below the line is not a priority — it is a distraction."
Winning proposition sounds generic	Read it back and ask: "Could every company in your industry say this? Then it is not a winning proposition."
Priorities are operational, not strategic	Ask: "If you succeed at this, does it fundamentally change your competitive position? Or does it just keep the lights on?"

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Phase 3: ALIGN Sessions

Duration: 2 hours per session, 1-2 sessions

Session Structure

Agenda

1. (10 min) Recap priorities — display the Canvas. Confirm the 5 priorities are still correct.
2. (60 min) Gap statements — for each priority, work through the four dimensions:
   • Structure and Process: what organizational changes are needed?
   • People: what capabilities must we build or acquire?
   • Culture: what behaviors and beliefs must shift?
   • Measures and Rewards: what should we measure and incentivize?
   Write each gap as: "Current State: [specific, honest] to Future State: [specific, measurable]"
3. (20 min) Prioritize gaps — not all gaps are equal. Identify which are most critical and which have the most dependencies.
4. (15 min) Reality check — are these gaps closable with the resources and timeframe available? If not, adjust scope or timelines.
5. (15 min) Transition to EXECUTE — preview the leadership message and action planning work.

When the Team Gets Stuck in ALIGN

Symptom	Intervention
Gap statements are aspirational, not specific	Ask: "How would you measure whether this gap is closed? If you cannot measure it, you cannot manage it. Rewrite it."
Team avoids the people conversation	Ask: "Do we have the right people in the right roles for this strategy? If you could redesign the org chart from scratch, would it look like this?"
Culture gaps are ignored	Ask: "What does this organization actually reward today? Is that what this strategy needs it to reward?"
Team writes too many gaps per priority	Say: "Which of these gaps, if not closed, would make this priority fail? That is your critical gap. Start there."

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Phase 4: EXECUTE Sessions

Duration: 2-3 hours per session, 1-2 sessions

Session 1: Leadership Message and Action Planning

Agenda

1. (10 min) Full strategy recap — walk through the Canvas from LEARN to ALIGN. This is the last time to confirm alignment before moving to action.
2. (40 min) Leadership message — craft the What, Why, How, and How Much. Apply the elevator test: can the CEO explain this in 60 seconds? Keep iterating until it passes.
3. (50 min) Action planning — for each priority, define:
   • Top 3-5 actions with specific owners
   • Due dates and milestones
   • Required resources
   • Success metrics
4. (20 min) Short-term wins — identify 2-3 actions that can produce visible results within 30 days. These build credibility and momentum.

Session 2: Resistance and Launch Planning

Agenda

1. (10 min) Recap action plans — confirm owners and timelines from Session 1
2. (30 min) Resistance mapping — who will champion this, who will resist, who is on the fence? For each blocker or skeptic in the org chart, plan a specific approach. Use Living Company AI's strategic alignment data from the org chart.
3. (30 min) Communication cascade — how will the leadership message reach every level of the organization? Plan the first three communication touchpoints.
4. (20 min) Execution dashboard setup — walk the team through the execution dashboard. Show them KPIs, milestones, action items, and how progress will be tracked.
5. (15 min) Review cadence — agree on the rhythm. Weekly 30-minute check-ins on action progress. Monthly 1-hour strategy reviews using the dashboard. Quarterly full cycle review.
6. (15 min) Close and next steps — confirm the first short-term win target. Set the first check-in date.

When the Team Gets Stuck in EXECUTE

Symptom	Intervention
Leadership message is too complex	Say: "Explain this strategy to me as if I am a new employee on my first day. You have 60 seconds." Then use what they say verbally — that is the real message.
No clear owners for actions	Ask each priority owner: "If this priority fails in 12 months, whose desk does that failure sit on? That person owns the actions."
Team underestimates resistance	Ask: "Who in this organization has the most to lose from this strategy? What would you do if you were them?"
No short-term wins identified	Ask: "What is the smallest, most visible thing you could accomplish in 30 days that would make the rest of the organization believe this is real?"

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Post-Engagement: Keeping the Cycle Alive

The engagement does not end when the EXECUTE sessions are complete. To keep the Strategic Learning cycle turning:

1. Configure weekly alerts — set up automated weekly execution summaries for the client team through the platform
2. Schedule quarterly reviews — use the strategy review feature to assess progress, test assumptions, and detect drift
3. Monitor the execution dashboard — check health scores, KPI trends, and milestone progress between sessions
4. Flag when a new LEARN cycle is needed — significant market changes, competitive disruptions, or strategy drift scores above 30 signal it is time to re-enter the LEARN phase

The measure of a successful engagement is not a beautiful strategic plan document. It is whether the organization is making different decisions six months later because of what they learned. Keep that standard front of mind.