Being a leader often means making far-reaching decisions that require major investments of time, resources, and energy. Complete certainty is seldom possible. Competing agendas often complicate the process. The future is never something you can take for granted. So you need to be as dispassionate as possible in how you examine opportunities and vulnerabilities. Knowing how to ask the right questions is essential to sorting through the options, clarifying objectives and making the best decision possible. 

Good leaders are adept at asking strategic questions. These are the types of questions that deepen understanding and look over the horizon. By asking more of these questions – of yourself and others — you articulate goals, set benchmarks and assess risk. You become a better thinker and a smarter leader. 

Strategic questions zoom out and look at the big picture. They ask about long-term goals, interests, and priorities. They consider alternatives, consequences, and downsides. They sharpen the focus on the larger objective and clarify what it will take to get there. Strategic questions break into distinct categories.

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 about the mission. What’s in play? What’s at stake? What is the strategic, long-range purpose or objective? Ask whether everyone is even ready to think strategically. 

Cost and Consequence:
How will you achieve your objective? What exactly is involved? What will it cost? What are the downsides? If you don’t succeed, what are the consequences? How will they affect your business, bottom line, organizational profile, personal happiness, or real-world activities? Get specific. Ask how your plan and its component pieces will measure strategic objectives against metrics and outcomes, time and resources. 

Trade-offs:
What are you not thinking about? Trade-offs are built into any big decision. For example, 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 winners and losers. These are questions that require you to challenge groupthink, conventional wisdom, and your own biases. Think of them as circuit breakers in your strategic questioning. If the tradeoffs are too extreme, or the downsides too severe, you may need to start over. 

Alternatives:
Is there another way? Ask about options that can achieve the same outcome. Keeping your strategic objective constant, ask whether different tactics can lower the cost or raise the prospects of success. Ask how tradeoffs and risks can be minimized through different approaches and timelines. 

Define Success:
What will success look like? How will you measure it? Over what period of time? As any good military commander relentlessly asks about the “end state,” what “mission accomplished” really looks like, you should ask what success means to you, to your team and what it will take to get there. Is the goal in your best interests? Who will it help? How? Be sure answers are clear, commonly understood, and widely shared. These questions prompt answers that navigate, set sights, and articulate a vision. 

Listen:
If you ask and don’t listen, you’re wasting everyone’s time. Invite questions from a wide range of perspectives. Then listen closely, actively. Listen for unexpected obstacles or unexplored risk. Listen for scenarios that call for additional consideration. Listen for gratuitous compliments that suggest pandering, or qualified agreement that may conceal deeper problems or doubts. Listen for indications that people don’t understand the purpose, the mission, or the goal. Listen for opportunities you hadn’t thought of. Intent listening will help you determine whether you’re on track or whether the strategy is flawed and 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, your goals, or your tactics. Ask them to list the downsides and the risks as well as the upsides and the advantages. Answer questions with more questions to dig deeper. Limit your comments and questions to 30 percent of the meeting, so others are speaking (and you are listening) 70 percent of the time. What do you hear? 

CEOs are often the most successful people. Many of them possess a hidden skill – the ability to ask questions that help envision the future, assess risk and reward, and anticipate trends.

First published on Leading Blog:
http://www.leadershipnow.com/leadingblog/2017/02/asking_the_right_questions_oft.html