Consider a few common scenarios:
- You’ve been invited to join a startup venture. You like the people. They have a couple of years of funding. The business plan is exciting. There could be a big payoff. But the idea is untested. The competition is moving fast. You’ll have to leave your corporate job, and there’s no job security in the startup world.
- Your company is discussing a major investment in a product that it believes will increase market share. You have to weigh in. Something is needed because the competition is eating your lunch and just landed a brilliant ad campaign that brought them a ton of buzz. Maybe the new product will make a difference, but it will require a huge investment, a lot of your time, and a big marketing push. It seems pretty cool, but there’s no guarantee it will be the blockbuster you need.
Get the big picture. Define the challenge or opportunity. Ask why it matters. Articulate the goal. Does it reflect your values? Who else cares? What are others prepared to do? What does it look like from 60,000 feet?
Define your plan. Determine the tactics that will help you achieve your strategic goal. What are the next steps down the road? Who does what? And how will you measure success along the way? Know that tactics change even as your strategic interests remain constant.
Challenge yourself. Hold your plan or proposal up to the light and look for holes. Play out different scenarios. What haven’t you thought of? What can go wrong? Can you explain and defend the strategy with facts, or is emotion driving you? Force yourself to stop and ask about options and alternatives.
Define success. Can you explain what success looks like? How will you know when you achieve it? What will it take and at what cost? Your success will depend on having asked the right questions so you have the most accurate “estimate of the situation” possible.
Strategic questions deepen understanding and clarify objectives. By asking more, you set benchmarks and assess risk. You examine opportunities and expose vulnerabilities. You become a better thinker and a smarter leader. You avoid the constraints of near-term distractions and stay focused on the essential, long-term goals.
In today’s digital world, it is more critical than ever that we ask, and ask more.