Recently, a company I advise invited me to join their strategic planning session. I declined, not to be contrarian, but to start a conversation. I’ve grown skeptical of traditional strategic planning. Too often, it gives leaders a false sense of control, a comforting illusion that the future can be mapped with precision. It begins with the assumption that we already know the path forward, that if we just get the plan right, success will follow. But in my experience, that mindset can stifle curiosity, dull creativity, and close us off from what’s actually happening in the market.

Instead of strategic planning, I’ve come to believe in strategic questions.

Questions are expansive. They challenge assumptions, expose blind spots, and invite imagination. The right questions can unlock latent enterprise value and reframe how a team sees opportunity. They shift the focus from what we think we know to what we’re still curious about. While plans can narrow our view, questions open it wide.

So rather than spending hours finalizing a plan, what if your team gathered to identify and explore the most critical questions facing the business? What if the next 12 months weren’t about predicting outcomes but about testing hypotheses and running thoughtful experiments to uncover insight?

Try questions like:

• What can we be doing that no one else is doing? 
• What aren’t we willing to do to drive growth, and why? 
• What should we be doing to triple household penetration? 
• What are we doing out of habit rather than strategy? 
• What bottlenecks or limiting beliefs exist within our leadership team? 
• What would we do differently if we knew the category was going to change completely in three years? 
• What decisions are we avoiding because they make us uncomfortable? 
• What would it look like to create 10x more value with the same resources? 

These questions don’t deliver answers; they provoke insight. They slow the rush to execution and create space for real thinking. They also nurture a culture of curiosity and humility, where exploration is valued as much as execution. That’s where the real strategic advantage lives.

The most resilient, high-performing companies I work with don’t fall in love with their plans; they fall in love with their questions. They use those questions as scaffolding for discovery, iteration, and growth. When you stay in the question, you remain alert and adaptable to whatever the market brings.

So before your next offsite or multiday planning session, pause and ask something different:

What are the three to five questions that, if answered, would fundamentally change how we operate, grow, and lead?

If you can ask better questions and give your team permission to explore them, you’ll likely end up with a far more valuable outcome than any traditional plan could offer.