"What would you do if you were CEO?"
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It’s the single most powerful question you can ask your leadership team ahead of a strategic planning session. Yes, every leader comes in with their own set of responsibilities—sales, operations, finance, product—and it’s natural to approach planning through the lens of their role.

But the invitation here is different: step outside of your function and take a broader view. If you were running the business—not just your part of it—what would you focus on? What risks would you take? What would you stop doing?

That shift in mindset changes everything.

When each leader takes time in advance to reflect on the business from the CEO seat, you unlock insights that would never surface in the room. You get sharper thinking, stronger alignment, and more meaningful strategy discussions.

Why This Question Works

Thinking like a CEO forces people to zoom out. Instead of advocating for their own teams or pushing departmental priorities, they have to wrestle with tradeoffs, complexity, and the bigger picture. It invites humility, creativity, and accountability.

And it clears the path for honest, focused dialogue in the room—because everyone has already done the deep thinking, individually and without performance pressure.

So How Do You Get There?

At Katahdin Group, we bake this question into the pre-work we assign before every strategic planning offsite. Pre-work is simply structured thinking—done solo, in advance—that sets the stage for a more productive conversation.

We ask every executive to spend a few hours answering questions like:

• If you were CEO, what would your top priorities be?
  
• What opportunities in the market should we be pursuing?
• What are our biggest risks or weaknesses?
• What 3–5 company-wide goals should we focus on next year?
• How do you think we did against last year’s goals—and what would you do differently?
• How aligned is the organization with our strategy, and what could improve that alignment?
  
  

These questions are deliberately not role-based. They're designed to get each leader thinking like an owner and stepping into the broader future of the business.

Why It Matters

Without this kind of preparation, the first day of an offsite often gets eaten up by brainstorming and alignment exercises. You burn valuable hours figuring out what the conversation should be—rather than actually having it.

But when the team walks in with clear, well-considered perspectives, you start the offsite already in motion. You spend less time generating ideas and more time stress-testing them, making decisions, and defining a plan.

And the quality of the conversation goes up. Because the thinking is better. The perspective is broader. The stakes feel shared.

One Small Shift, One Big Outcome

You don’t need dozens of exercises or complicated frameworks to run a great strategic offsite. But you do need your team to show up thinking like a CEO.

That mindset—when nurtured through thoughtful pre-work—can be the difference between a plan that sits on a shelf and a strategy that actually moves the business forward.

So before your next offsite, try this:

Share the question early, give people time to reflect, and compile the input into a format the whole team can absorb. Then watch what happens when the entire team starts thinking like the CEO.

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These insights are drawn from the Strategic Ascent system, which helps CEOs and leadership teams build alignment through a structured planning process that leads to action—and ownership.

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