Facilitator guide
Facilitator guide
A complete run-of-show for delivering the Playing to Win AI Strategy Sprint independently. Includes scripted cascade questions, exercise instructions, the "What Must Be True" technique, AI Canvas walkthroughs, objection handling, and energy management tips.
Six modules across four hours, with two breaks. Total facilitation time: 3 hours 30 minutes. Every module maps to one or more questions in the Strategic Choice Cascade.
Thorough preparation is the difference between a good sprint and a transformative one. Follow this timeline to ensure nothing is left to chance.
The physical environment shapes the quality of the conversation. This is an executive sprint — boardroom energy, not classroom energy.
Boardroom or conference style. Everyone around one table, 6–10 seats. No classroom rows. Every participant must be able to see every other participant and the wall canvas simultaneously.
Set the tone immediately: this is not an AI workshop. This is a strategy session that happens to be about AI. You are establishing that most organizations do not have an AI strategy — they have an AI wish list. The provocation should create slight discomfort, which fuels energy for the rest of the sprint.
Present each trap with a brief example. Watch for recognition in participants' faces — that is your signal that the provocation is working.
Close with the Lafley line: "Playing to play — rather than playing to win — leads inevitably to mediocrity."
"Based on what you saw in the pre-work and what you just heard, I want each of you to identify which trap — or traps — your organization currently falls into. Be honest. There is no judgment here; every organization starts in at least one of these traps."
Most groups will cluster around Trap 4 (optimizing the status quo). If they do, use this: "That is perfectly natural. But notice what it means: you have been asking 'how can AI improve what we already do?' instead of 'what should we be doing differently because AI exists?' That is the shift we are going to make today."
The winning aspiration is the first question in the cascade. It sets the direction for everything that follows. Critically, it must be:
Executives often resist being specific at this stage because specificity feels risky. That is the point. Reassure them: "We can revisit and refine this. But we need a starting point that is sharp enough to test. A vague aspiration cannot be tested."
"Write a one-sentence winning aspiration for your organization's AI strategy. Complete this sentence: 'We will win by using AI to...' Make it customer-centric. Make it specific. Make it uncomfortable."
"Pair up with the person next to you. Share your aspirations. Your job is to challenge each other with two questions:"
"Now let us bring it together. Each pair shares their best aspiration. We are going to converge on one shared winning aspiration for this organization."
Capture aspirations on the wall canvas under Q1. Guide the group toward synthesis — not averaging. Look for the aspiration that creates the most energy and the most useful exclusion.
"Where to Play" covers multiple dimensions. For Microsoft Partners serving SMEs, these dimensions are particularly relevant:
Draw a large 2x2 matrix on the wall or flip chart:
Label the quadrants:
"Each of you: write your key client segments, markets, or technology areas on separate sticky notes. One per sticky note. Then place each one on the matrix based on your honest assessment of client need and your right to win."
Walk the room. If participants cluster everything in the top-right, challenge them: "If everything is high-priority, nothing is."
Guide the discussion with these questions:
Force the choice: circle the top 2–3 "Where to Play" areas on the cascade canvas. Then — this is the hard part — explicitly name what you are NOT doing. Write "Where We Will NOT Play" on the canvas and list the exclusions.
This is often the most heated part of the sprint. Executives resist excluding things because exclusion feels like leaving money on the table. Use this line: "Choosing does not mean abandoning. It means leading with your strongest proposition. The rest can follow once you have won in your primary battlefields."
Porter's two generic strategies still apply: cost leadership or differentiation. But AI creates specific ways to win that go beyond traditional frameworks:
Distribute the printed AI Canvas template. Explain the 7 elements:
"For each of your top 2–3 'Where to Play' choices, complete one AI Canvas. Focus on the most important client decisions in that space."
Work in pairs or small groups. Each pair takes one "Where to Play" area and maps the key decisions, predictions, and judgments. Walk the room and help groups that get stuck on the distinction between prediction and judgment.
Each pair presents their AI Canvas in 90 seconds. Capture the key decisions on the cascade canvas under Q3. These canvases become the foundation of the AI Decision Map deliverable.
The most common mistake is confusing prediction with action. A prediction is "this client is likely to churn." The action is "offer them a retention package." The judgment is "should we invest in retaining this client, or is the cost too high?" Help participants separate these cleanly.
"For our How to Win choices to work, certain things must be true. Let us surface those assumptions now — before we invest. For each assumption, ask: what must be true about..."
Two questions remain in the cascade. They are often combined because they are deeply interrelated:
For Microsoft Partners, capability questions are concrete: which Microsoft competencies and certifications? What partner tier? What hiring profile? What data infrastructure?
"Based on your Where to Play and How to Win choices, what are the 5–7 core capabilities your organization needs? Think about:"
"For each capability, rate on a 1–5 scale:"
Use the printed Capability Gap template. The gap between current and required is the investment priority.
"Identify the 2–3 biggest gaps. These become your investment priorities. Then for each: what management system sustains progress?"
Groups often underrate their current capabilities (false modesty) or overrate them (blind spot). Challenge both. Ask: "Would your clients agree with that rating? Would your best competitor?" External perspectives are more honest than internal ones.
"Same technique as before. For your capability plan to work, what must be true about:"
Capture assumptions quickly. These are operational risks that need to be tracked post-sprint.
Guide the group through synthesizing all five cascade answers onto one page. Use the wall canvas or a large flip chart. The format from top to bottom:
Read through each element aloud. After each one, ask the group: "Does this still feel right? Would you defend this choice to your board?" If yes, move on. If not, sharpen it.
This is the deliverable the executive team takes back to their organization. It must be crisp enough that someone who was not in the room can read it and understand the strategy. If an element requires explanation, it is not clear enough yet.
From Switch: "Shrink the Change." When the gap between current state and desired state feels overwhelming, people freeze. The antidote is to identify the smallest possible first steps that create momentum.
"Identify 3 concrete actions. For each, define:"
Quick wins only. These should build momentum, not tackle the biggest capability gaps. Save the big moves for a properly resourced implementation plan.
Examples of good 30-day actions:
"Before we close, I want to go around the table. Each of you: state your personal 30-day commitment aloud. Not your team's commitment. Yours. What will you personally do in the next 30 days to advance this strategy?"
This is not optional. Public commitment creates accountability. If someone says something vague, gently push for specificity: "What exactly will you do, and by when?"
Six common objections you will encounter during the sprint. Memorize the responses — they are grounded in the Playing to Win framework and should feel natural, not scripted.
Response: "Choosing does not mean abandoning. It means leading with your strongest proposition. P&G chose 10 categories out of 100+ to dominate. They did not exit the other 90 — they just did not lead with them. Your chosen battlefields get your best people, your most investment, your sharpest positioning. The rest gets what is left."
Response: "That is Strategy Trap number 3. Playing to Win is not a fixed plan — it is a set of choices you revisit. But without choices, you have no basis for any decision. Think of it as a compass, not a GPS route. The direction stays consistent even when the road changes. Build a system to revisit quarterly, and adapt."
Response: "Strategy is not about size, it is about choices. A 15-person firm that picks 2 industries and 1 Microsoft technology to master will outperform a 50-person firm that says yes to everything. In fact, smaller firms benefit MORE from strategy because they have less room for waste. Every hour your team spends on the wrong thing is an hour they are not spending on the right thing."
Response: "Competing by being a smaller version of a larger company is the definition of playing to play. Where can you be DIFFERENT, not just cheaper? Your size is an advantage if you choose well — you can move faster, specialize deeper, and build closer relationships than a company that serves everyone."
Response: "That is a platform choice, not a strategy. 30,000+ Microsoft partners made the same choice. Where to Play asks: which Microsoft technologies, for which clients, solving which problems? Being a Microsoft partner is necessary but not sufficient. The strategy is in the specifics."
Response: "Then you are choosing to let the market decide for you. Playing to Win says: make the best choice you can now, build a system to revisit it quarterly, and adapt. The cost of indecision is not zero — it is the accumulated drift of making reactive, uncoordinated decisions. Indecision is the worst strategy of all."
A half-day sprint has a compressed energy arc. Manage it deliberately or lose the room in the final module — exactly when commitments happen.
Energy is typically high at the start. The main risk is analysis paralysis in Module 2 — executives overthinking the winning aspiration. If the group gets stuck wordsmithing, interrupt: "This does not need to be perfect. It needs to be specific enough to test. We can refine it after we see how it connects to the rest of the cascade."
Where to Play generates heat because choosing means excluding. This is good energy — productive disagreement. Let it run, but time-box it. If the group cannot narrow to 2–3 choices, use a dot-vote: each person gets 3 dots, place them on the matrix. The pattern usually resolves it.
The first 90 minutes are the most intense. Participants need to reset before the intellectually demanding Module 4. Do not skip this break. Do not shorten it. Let people check their phones, process what they have heard, and come back ready for the next phase.
How to Win is the most intellectually demanding module. The AI Canvas exercise is your tool to keep it structured and prevent it from becoming abstract. Walk the room actively. If a pair is struggling, sit with them for 60 seconds and help them identify the first decision to map.
Energy often dips here as participants realize the gap between aspiration and reality. This is natural and productive. Channel it into honest capability ratings rather than letting it become discouragement. The message is: "Knowing the gap is the first step to closing it."
Keep momentum high. This is where commitments happen and where the strategy becomes real. If energy is dipping, stand up. Walk to the cascade canvas. Point to specific choices and say: "This is what you built. This is yours. Now let us make sure it does not die in a drawer." The closing commitments must be spoken aloud — public accountability is the engine.
Five polished deliverables that turn the sprint into lasting organizational value. These are what the client pays for — the sprint is the process, but the deliverables are the product.
Polished one-page cascade with all 5 answers. Winning Aspiration at the top, Management Systems at the bottom. Includes an explicit "Where We Will NOT Play" section — this is what separates it from a generic strategy statement. Designed to be shared with the broader organization, board, or investors.
Visual map of key client decisions where AI prediction creates competitive advantage. Built from the AI Canvas exercises in Module 4. Shows, for each chosen "Where to Play" area, the specific decisions, predictions, judgments, and data requirements. This is the bridge between strategy and implementation.
Pre-work diagnostic results with commentary on which traps the organization fell into and how the sprint addressed them. Includes specific recommendations for avoiding each trap going forward. Useful for communicating the "before and after" to stakeholders who were not in the room.
Three concrete actions with owners, deadlines, and success metrics. Each action is specific enough to execute without further interpretation. Includes the "What Must Be True" assumptions that were surfaced during the sprint — these should be tracked as strategic risks.
Analysis of how the chosen strategy differentiates from 2–3 key competitors. Shows where the strategy creates unique positioning and where competitors might respond. Based on the "What Must Be True" assumptions about competitors from Module 4.