Playing to Win — AI Strategy Sprint

The Problem

Most organizations play to play — not to win

Most organizations "do AI" without making real strategic choices. They spread resources across too many initiatives, copy what competitors are doing, and avoid the hard trade-offs that strategy demands.

Playing to play leads to mediocrity. Strategy is not about doing more — it is about choosing what NOT to do. Yet executive teams routinely fall into one of four strategy traps that prevent them from making those choices.

This workshop forces the conversation that most organizations avoid: where exactly will we compete with AI, and what gives us the right to win?

Trap 01

The Do-It-All Strategy

Mistaking a broad vision for a strategy. "We will be an AI-driven organization" sounds bold but says nothing about where to focus or what to sacrifice.

Trap 02

The Don Quixote Strategy

Mistaking a plan for a strategy. A 50-page AI roadmap with Gantt charts is not strategy — it is a plan that avoids the question of winning.

Trap 03

The Waterloo Strategy

Denying that long-term strategy is possible in a fast-moving AI landscape. "Things change too fast to plan" becomes an excuse for making no choices at all.

Trap 04

The Ivory Tower Strategy

Optimizing the status quo instead of making new choices. Automating existing processes with AI is not strategy — it is incremental improvement.

Before We Start

Pre-workshop preparation

Great workshops are won before the day. Every participant arrives prepared, aligned on language, and with skin in the game.

1 week before · 10 min

Strategy Trap Diagnostic

Digital self-assessment sent to each executive. Are we playing to win or playing to play? Which of the 4 strategy traps do we fall into? Results are anonymized and presented during the workshop to create honest, data-backed conversation.

1 week before · 30 min

Executive Intake Call

Brief call with the workshop facilitator to understand strategic context, competitive landscape, and current AI positioning. This ensures the workshop is tailored, not generic.

1 week before · 20 min

AI Decision Inventory

Pre-filled template: list your top 10 business decisions. For each one — how is this decision made today? What data informs it? What would change with perfect prediction? Based on the Prediction Machines framework.

5 days before · 5 min read

One-Page Briefing

Executive summary of the Playing to Win framework and the AI Canvas methodology. Ensures everyone shares a common vocabulary before walking into the room.

Workshop Day

The agenda

Four hours. Six blocks. Five strategic choices. One page that defines your AI strategy.

09:00 – 09:30 · 30 min

Block 1

The Strategy Trap

Present the 4 strategy traps from Playing to Win. Share anonymized diagnostic results from the pre-workshop assessment. Honest self-assessment: which trap are we in? Create urgency for making real choices.

Output: Shared baseline & urgency

09:30 – 10:00 · 30 min

Block 2

Winning Aspiration

"What does winning with AI look like for us — not participating, winning?" Reframe from "adopt AI" to a specific, ambitious outcome. Introduce the Prediction-Judgment split from Prediction Machines: what decisions would you make differently with perfect prediction?

Output: One winning aspiration statement

10:00 – 10:45 · 45 min

Block 3

Where to Play

Which markets, segments, customer types, and processes will we target with AI? Equally important: where will we explicitly NOT play? Use the AI Canvas from Prediction Machines to identify the highest-value decisions in your value chain.

Output: Where-to-Play choices on one page

10:45 – 11:00 · 15 min

Coffee break

11:00 – 11:45 · 45 min

Block 4

How to Win

What is our distinctive right to win? Apply Treacy & Wiersema: are we building AI for Operational Excellence, Customer Intimacy, or Product Leadership? What makes us different from every competitor who also has access to GPT?

Output: How-to-Win statement

11:45 – 12:15 · 30 min

Block 5

Capabilities & Systems

What must be true for our choices to work? Map required capabilities — data infrastructure, talent, governance, culture — and management systems: KPIs, budgets, decision rights. Turn aspiration into organizational requirements.

Output: Capability requirements list

12:15 – 12:45 · 30 min

Block 6

Script the Critical Moves

From Switch (Heath & Heath): don't leave with a strategy deck — leave with 3 specific, concrete actions for the next 30 days. Not "build AI capabilities" but "hire a data steward by April 15." Each action gets an owner and a deadline.

Output: 30-day action sprint with owners

Built On

Theoretical foundations

This workshop is not opinion-based. It combines three peer-reviewed strategy frameworks into a single, integrated methodology.

Playing to Win

A.G. Lafley & Roger Martin

The Strategic Choice Cascade: 5 questions that define any strategy. Winning aspiration, where to play, how to win, capabilities, and management systems.

Prediction Machines

Agrawal, Gans & Goldfarb

AI Canvas and the Prediction-Judgment-Action framework. Reframe AI as a prediction technology and identify where cheap prediction creates the most value.

Switch

Chip Heath & Dan Heath

"Script the Critical Moves": translate strategy into concrete, actionable first steps. Overcome analysis paralysis by defining the next 30 days in specific terms.

What You Get

Post-workshop deliverables

You leave the room with clarity. Within 7 business days, you receive the complete documentation to present, align, and execute.

AI Strategy on a Page

The completed 5-question cascade as a single-page strategic document. Professional design, ready for board presentation. Delivered as editable PowerPoint and PDF.

AI Decision Map

Top 5–10 business decisions where AI-powered prediction creates the most value, with current vs. future state analysis. Based on the AI Canvas exercise.

Strategy Trap Report

Pre-workshop diagnostic results with analysis: which traps the executive team falls into, patterns across respondents, and specific recommendations to avoid each trap.

30-Day Action Sprint

3–5 scripted critical moves with owners, deadlines, success criteria, and escalation paths. Designed to create immediate momentum after the workshop.

Competitive Positioning Brief

How the chosen Where-to-Play and How-to-Win positions the organization relative to key competitors. Includes differentiation opportunities and risk areas.

All deliverables delivered within 7 business days after the workshop.

Investment

Pricing

AI Strategy Sprint

EUR 7,500

Starting from · excluding VAT

✓ Pre-workshop diagnostic & executive intake call
✓ Half-day facilitation (4 hours, on-site)
✓ All 5 post-workshop deliverables
✓ 1 follow-up call (30 min) to review progress

Optional Add-On

Quarterly Strategy Review

Revisit the cascade every quarter. Are we still playing to win? Update choices based on market shifts, new capabilities, and competitive moves.

EUR 2,500 / session

Optional Add-On

Deep-Dive on One Cascade Element

Half-day working session focused on a single element of the cascade — such as a detailed Where-to-Play analysis or a capability-building roadmap.

EUR 4,000 / half day