Ask More: The Power of Questions to Open Doors, Uncover Solutions, and Spark Change

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STRATEGIC QUESTIONS

You’re about to make a major decision that will affect your life, your business, or your community. You’re considering a move, and it requires a big investment of time, resources, and energy. Your future is on the line. Strategic questions zoom out and look at the big picture. They ask about long-term goals, interests, and priorities. They consider alternatives, consequences, and risks. These questions sharpen the focus on the larger objective, the higher calling, and clarify what it will take to get there.

The Big Question:

What are you trying to do? Why?

What difference will it make?

Start at 20,000 feet. The Oxford Dictionary defines strategic as “relating to the identification of long-term or overall aims and interests and the means of achieving them.” Ask whether everyone is even ready to think strategically. Ask about the mission. What’s in play, what’s at stake, and what is the strategic, long-range purpose or objective?

Cost and Consequence: How will you achieve your objective? What will it cost? What are the downsides? Now that you’ve defined the goals, ask about their consequences. How will they affect the business, the bottom line, the organizational profile, personal happiness, or real-world activities? Get specific. What’s the cost? Ask how your plan and its component pieces translate strategic objectives into metrics and outcomes based on the time, resources, and objectives. Ask who you would help if you succeeded.

Trade-offs: What’s the downside? What are the risks? What are you not thinking about? Trade-offs are built into any big decision: You can make more money but will have less free time; you can fix the bottom line but will have to lay off workers; you can liberate a country but will cause damage and death. Trade-off questions openly, sometimes defiantly, ask about risk and downsides. They ask people to calculate when there are no formulas. These are questions that challenge groupthink, conventional wisdom, and your own biases. Think of them as circuit breakers in strategic questioning.

Alternatives: What are your options? Is there another way? Ask about options that can achieve the same outcome. Keeping your strategic objective constant, ask whether there are different tactics that can lower the cost or raise the prospects for success. These questions take the tradeoffs and the risks and ask how they can be minimized by applying different approaches and timelines.

Define Success: How will you know when you get there? What will success look like? How will you measure it? Any good military commander relentlessly asks about the “end state”: what “mission accomplished” really looks like. Ask what success means and what it will take to get there. Be sure answers are clear, commonly understood, and widely shared. These questions are the cornerstone of strategic thinking. They clarify destination and set expectations. They help navigate, set sights, and articulate a vision.

Listen: Invite questions from a wide range of perspectives. Listen closely for unexpected obstacles or unexplored risk. Listen for scenarios that call for additional consideration. Listen for gratuitous compliments or qualified agreement that conceal deeper problems or concerns. Listen for indications that people don’t understand the purpose, the mission, or the goal. That will help you determine whether it’s just the message that needs to be sharpened or whether the strategy itself needs to be rethought.

Try: Engage a group about your big idea. Explain the reasoning behind it. Then ask everyone to challenge you, your logic, and your tactics. Answer questions with more questions. Limit your comments and questions to 30 percent of the meeting, so others are speaking and you are listening 70 percent of the time.