Pre-work
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Playing to Win -- AI Strategy Sprint

Your pre-work kit

Complete these four tasks 1-2 weeks before the sprint. They take about 25 minutes total and ensure your leadership team arrives ready to make real strategic choices.

Progress 0 of 4 complete
1
Trap Diagnostic
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Decisions
3
Positioning
4
Reading
Task 1 of 4

Strategy Trap Diagnostic

Based on Playing to Win by A.G. Lafley and Roger Martin. Most organizations fall into common strategy traps without realizing it. Rate your agreement with each statement to discover which traps may be active in your organization.

~5 minutes
Statement 1
"Our AI strategy is primarily a vision statement or set of aspirations."
Trap: The Do-It-All / Vision trap
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Strongly disagree Strongly agree
Statement 2
"We have a detailed AI implementation plan but haven't defined what winning looks like."
Trap: The Don Quixote / Plan trap
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Strongly disagree Strongly agree
Statement 3
"We believe AI is moving too fast to commit to a specific strategy."
Trap: The Waterloo / Denial trap
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Strongly disagree Strongly agree
Statement 4
"Our AI efforts focus on improving what we already do rather than creating new competitive advantages."
Trap: Status quo optimization
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Strongly disagree Strongly agree
Statement 5
"We're following the same AI approach as our main competitors."
Trap: Best practices / Sameness
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Strongly disagree Strongly agree
Statement 6
"Different leaders in our organization have different views on what our AI priorities should be."
Trap: Lack of alignment
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Strongly disagree Strongly agree
Statement 7
"We've invested in AI tools but can't clearly articulate the competitive advantage they create."
Trap: Technology-first
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Strongly disagree Strongly agree
Statement 8
"We say yes to most AI opportunities that come our way."
Trap: No strategic filter
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Strongly disagree Strongly agree
Task 2 of 4

AI Decision Inventory

Based on Prediction Machines by Agrawal, Gans & Goldfarb. AI creates value by improving predictions that feed into decisions. Map the key decisions in your business areas to discover where AI could have the highest impact.

~10 minutes
Sales -- Which prospects to prioritize
Currently: Experience/gut feel · Could prediction help? Yes
Operations -- When to reorder inventory
Currently: Rules/SOPs · Could prediction help? Yes
Customer Service -- How to route client issues
Currently: Rules/SOPs · Could prediction help? Maybe
Task 3 of 4

Competitive Positioning Input

Strategy is about making choices that create competitive advantage. These three questions will surface the raw material for the "Where to Play" and "How to Win" cascade questions during the sprint.

~5 minutes
Task 4 of 4

Reading Brief

A 2-minute introduction to the Playing to Win framework. Read through this before the sprint so your team has a shared language and shared expectations.

~2 minutes

What is the Strategic Choice Cascade?

The Strategic Choice Cascade, developed by A.G. Lafley and Roger Martin, is a framework of five integrated questions that together form a real strategy. Unlike vague mission statements or long lists of initiatives, the cascade forces you to make specific, interconnected choices that reinforce each other.

The five questions build on each other -- you cannot answer one without considering the others. This is what makes it a strategy rather than a wish list.

1. What is our winning aspiration?
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2. Where will we play?
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3. How will we win?
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4. What capabilities must be in place?
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5. What management systems are required?

"Playing to play" vs. "playing to win"

Most organizations "play to play" -- they participate in their market, follow best practices, and try to keep up. Playing to win is fundamentally different. It means making deliberate choices about where you will and will not compete, and building specific advantages that competitors cannot easily replicate.

Applied to AI: most companies are "playing to play" with AI -- deploying tools because competitors are, running pilots without clear strategic intent, or spreading investment thinly across too many opportunities. Playing to win with AI means choosing specific domains where AI creates competitive advantage and concentrating effort there.

Why most AI "strategies" are traps

Lafley and Martin identify four common strategy traps. In the AI context, they show up everywhere:

  • The Vision Trap
    "We will be an AI-first organization" -- sounds inspiring but makes no choices.
  • The Plan Trap
    A detailed AI roadmap with milestones and budgets -- but no definition of what winning looks like.
  • The Denial Trap
    "AI is moving too fast to commit" -- so no strategy is made and the organization drifts.
  • The Status Quo Trap
    Using AI only to do what you already do, faster -- missing the chance to create new competitive advantages.

What to expect in the sprint

You will make real choices about where to compete and how to win with AI. This is not a brainstorming session -- it is a decision-making session.

In the half-day sprint, your leadership team will work through all five cascade questions together, applied to your AI strategy. You will define what winning looks like, choose specific markets and customer segments where AI gives you a right to win, determine your competitive advantage, identify the capabilities you must build, and design the management systems that sustain it all.

The pre-work you have just completed -- the Strategy Trap Diagnostic, your AI Decision Inventory, and your competitive positioning input -- will serve as the raw material for these exercises. Come prepared to make choices, not to brainstorm.

Pre-work complete

Your responses have been saved. The facilitator will use this input to tailor the sprint to your organization. Come ready to make real strategic choices.

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