Winning with AI: 5 Strategic Questions to Inspire and Lead Your Team

Ask these 5 Questions to be strategic, leverage AI in your business and drive innovation in your team

Image Credit: Author + AI

Great leaders stand out by asking the right questions. In a world driven by data and artificial intelligence (AI), this skill is more crucial than ever.

In my experience, separating signal from noise can mean the difference between a winning decision that shapes success and a misstep that leads to failure. See this article for a pivotal investment decision we made at PwC.

Asking the right questions is the key. Aligning AI with strategy drives progress, empowers teams to think bigger, act smarter, and deliver meaningful results.

Leaders who ask the right questions seize bigger opportunities and overcome challenges faster. They also build cultures that foster resilience and innovation well into the future.

Here are five key questions to ask your team to unlock the full potential of AI in your organization.

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1. How Can We Use AI to Improve Decision-Making Across the Team?

Why It Matters: AI uncovers insights and patterns that sharpen decision-making, but human judgment remains essential.

Leaders must ensure AI is a strategic partner, not a substitute for critical thinking.

Executives spend nearly 40% of their time (McKinsey) making decisions.

Imagine the capacity unlocked when AI streamlines the process.

Takeaway: Empower your team to leverage AI-driven insights while maintaining clear, strategic decision-making.

2. Where Are We Using AI to Free Up Time for High-Value Work?

Why It Matters: AI thrives on automating repetitive tasks, freeing up bandwidth for teams to focus on innovation and creativity. Leaders must ensure AI is creating capacity for high-impact work, not just efficiency.

Takeaway: Leverage AI to identify and automate routine tasks, then restructure workloads to prioritize strategic initiatives and creative problem-solving.

3. How Can AI Help Us Better Understand and Serve Our Customers?

Why It Matters: AI can reveal powerful insights about customer behavior, preferences, and needs, enabling teams to deliver more impactful experiences.

Remember: customers aren’t always external—internal stakeholders are customers too. Leaders should ensure their teams think broadly about who they’re serving and how AI can make a difference.

Takeaway: AI isn’t just a tool for understanding customers—it’s a strategy for anticipating needs and delivering value at every level. Empower your teams to leverage AI-driven insights to improve engagement, optimize workflows, and strengthen relationships across the business.

4. What Risks Are We Overlooking in Our Use of AI?

Why It Matters: While AI offers significant advantages, it also brings risks like bias, over-reliance, or ethical dilemmas. Leaders should ensure their teams feel comfortable identifying risks and addressing them proactively.

Takeaway: Create a culture of transparency where teams regularly discuss the potential risks and ethical challenges of using AI.

5. How Are We Using AI to Innovate Beyond the Status Quo?

Why It Matters: AI isn’t just about efficiency—it’s a tool for unlocking creativity and identifying new opportunities. Leaders should challenge their teams to think beyond solving today’s problems and explore AI’s potential to innovate.

Takeaway: Foster a mindset of experimentation, where teams are encouraged to take calculated risks and test new ideas with AI.

Bottomline

AI won’t replace great leaders—it will amplify them.

The smartest leaders use AI to sharpen decisions, unlock time for strategy, anticipate needs, and drive innovation. In a world of endless data, those who question best will lead best.

Whenever you’re ready, there are 2 ways I can help you

1️⃣Strategy & Planning Bootcamp: Master the strategic mindset, problem-solving skills, and decision-making frameworks used by top leaders and management consultants to drive business success.

In this live, 3-week course, you’ll learn practical strategy frameworks and problem-solving techniques that apply to any business, industry, or leadership role.

Taught by Sam Liu, MBA Adjunct Professor at Columbia & Partner at Mercer, alongside me.

Learn more and enroll today.

2️⃣ Strategy Toolkit: The essential resource for evolving from a tactical operator to a strategic leader—without an MBA or consulting background.

Get top strategy frameworks and ready-to-use Notion templates to structure ideas, drive discussions, and make smarter decisions. Start leading strategically today with the toolkit.

Go for it!

Joselle

🔓 Unlock Exclusive AI Leadership Strategies

Asking the right questions is the first step. But the best leaders don’t just ask the right questions—they take strategic action based on AI-driven insights.

To help you turn AI into a leadership advantage, I’ve compiled four exclusive Pro Tips that will help you:

✅ Make AI-driven decisions accessible across your team
✅ Automate smarter to free up time for high-value work
✅ Stay ahead of customer needs using AI insights
✅ Build safeguards to manage AI risks effectively

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