Insightful Answers Come from Asking the Right Questions

“It’s not that they see the solution. They can’t see the problem.”

G.K. Chesterton

As a CEO, your vision is critical to your success. Your eyes are turned toward the horizon, and the more clearly you can see what’s ahead, the more capable you are of steering toward opportunity while keeping far away from the rocky shoals of undue risk. How do you get where you want to go? Sometimes it isn’t the answers you need; it’s the right questions.

Some companies’ cultures are question-averse. They see questioning as a challenge to the status quo, a means of upending the established order, and change isn’t always comfortable. Meaningful cultural change starts with you and the questions you ask – of your marketing team, of your sales personnel, of your CFO, and especially of yourself.

Asking, not Telling

How do you spot the right questions to ask, the ones that lead to real solutions? First, start by knowing what counts as a question.

C-level executives become very used to providing answers. They tell, explain, and decide as a matter of course. It’s part of your role to tell others what to do. That’s why it can be so difficult to step back and ask without pre-judging or discarding new ideas out of hand. To ask questions without telling the people you’re asking what answers you hope to hear is an important skill to develop for executives, yet it’s one that’s underused.

If your questions often start with “don’t you think…” or “Isn’t it true that…,” you’re telling more than you’re asking. Ask using positive, neutral language – “do you think…” and “what can you tell me about…” – will produce far more insightful answers.

Staying Focused

We’ve all been in one of those interminable meetings: the ones that are scheduled for an hour and run twice as long, yet most of that time’s spent worrying over a tiny fraction of the issue at hand. One reason why is that people get bound up with asking questions about minutiae instead of recognizing these questions as unintentional derailments and diversions from what matters most. Questions that come out of left field are similarly distracting. They aren’t necessarily wrong questions, but they’re ill-timed and lead a conversation away from where it needs to go. Sometimes that diversion happens for a reason, especially if the group’s avoiding a topic – unintentionally or otherwise.

Asking Difficult Questions

It’s not fun to talk about the biggest, most insurmountable problems your company’s facing, even if you’re talking about them with yourself. Asking around the problem can often lead into its heart, so start with questioning why the topic is sensitive or what could happen if you address it head-on. Reducing obstacles to solving the problems around the central issue is a good way to begin dismantling the larger problem itself.

Valuing Questions as Much as Answers

Not every question has a single definitive answer. Many of the questions that lead to the most creative, open-ended solutions have a virtually infinite number of answers. What’s important here is making room for the questions themselves. By allowing yourself and your personnel to question, you open up new possibilities that couldn’t have been reached only by a standard question-and-answer session.

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