Using AI to Supercharge Strategic Thinking and Execution
By Dr. James “Jim” Sartain and Dr. Kenneth “Robbe” Addis
Delivered at JWMI Connects | June 12, 2025
In a world shaped by disruption, complexity, and accelerating expectations, AI has emerged not as a threat to strategic thinking—but as a multiplier of it.
In our recent JWMI Connects session, we explored how generative AI tools can help leaders clarify, sharpen, and execute smarter strategies. Titled AI Meets Strategy: How Leaders Can Drive Smarter Decisions, our 40-minute workshop was built around practical use cases, live AI prompt demonstrations, and a simple but powerful idea:
Thefuture of AI is not about replacing humans; it's about augmenting human capabilities.
Sundar Pichai, CEO of Google
Five Questions, Now AI-Enhanced
We structured the session using the JWMI Five Strategic Questions:
- What does the playing field look like now?
- What has the competition been up to?
- What have you been up to?
- What’s around the corner?
- What is your game-winning move?
For each, we demonstrated how AI can accelerate research, surface risks, simulate market changes, and spark bold ideas. From competitive landscapes to customer segmentation, AI became a co-strategist—able to produce executive-ready insights in seconds.
Clarity and conciseness in presenting strategy is essential. Don't use thick, convoluted planning books and busy slides. Tell the story simply. The emphasis is on a "big a-ha" - a smart, realistic, and relatively fast way to gain a competitive advantage.
Jack Welch
Prompt Craft: The New Strategic Skill
We introduced participants to a five-part prompt structure—Role, Background, Instructions, Parameters and Output—and showed how this "chain-of-thought" technique powers more accurate, business-relevant AI output.
Attendees saw prompts simulate:
- A global EV market scan
- Streaming industry competitive timelines
- Internal reporting summaries
- Threat identification for LinkedIn
- Bold strategic moves for Costco
Prompts:
It wasn’t about asking ChatGPT random questions. It was about giving AI a seat at the strategy table—with structure.
A key takeaway: AI isn’t just for tech giants.
A small business owner asked:
“Can AI help me grow my online coffee company?”
Our answer: absolutely. With AI, even solo entrepreneurs can:
Draft content in your unique brand voice
- Engage customers with smart chatbots
- Customize product recommendations
- Optimize ad performance—faster and cheaper
The playing field is poised to become a lot more competitive, and businesses that don't deploy AI and data to help them innovate in everything they do will be at a disadvantage."
- Paul Daugherty, Accenture
Ethics, Accuracy & Human Judgment
AI doesn't have a moral compass. It doesn’t “know”—it predicts. That’s why responsible use is a leadership imperative.
Best practices we shared:
Pair AI with verified sources to avoid hallucinations
- Use AI to spark thinking, not replace it
- Maintain editorial oversight, especially in regulated contexts
Final Takeaway: Don’t Just Watch. Lead.
As we closed the workshop, we left participants with a charge:
Don’tjust watch the AI revolution, participate in it. Start using AI tools to unlocknew possibilities in your work and life.Leaders don’t need to be coders or futurists to start using AI. They just need curiosity, clarity, and the courage to experiment.
Don’t just watch the AI revolution, participate in it. Start using AI tools to unlock new possibilities in your work and life.
Fei-Fei Li, Professor of Computer Science at Stanford
Call to Action
Want to get started with AI-powered strategy in your organization?
✅ Download our free prompt guide
✅ Book a virtual team workshop with Jim & Robbe
✅ Follow us for more insights on strategy + AI
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