The Why, What If and How
of Creative Questions

The ability to ask creative questions has sparked innumerable inventions. Questions asked in the right way leads to breakthrough thinking and disruptive innovations, such as those created by Airbnb, Uber, Pandora, Foursquare, Twitter, Facebook, YouTube, iPhone and many others.

Author and journalist Warren Berger writes about this in A More Beautiful Question, a fascinating book illuminating the power of questions that lead to innovations. He outlines a framework of three sequential questions to spark the creative process:

Why? => What if…? => How might we…?

Ask “Why” and “What If”

The “why” stage is about stepping back and observing, to see and understand more fully what’s going on. Notice what others may be missing. Don’t ignore incongruencies. Investigate them. Challenge assumptions. Question the questions being asked and ask a new question.

To question well — in particular, to ask fundamental “why” questions — we need to stop doing, stop knowing and start asking, which makes most people uncomfortable. We don’t want to ask, “Why are we doing this, exactly?” We don’t want to slow down a meeting, or appear stupid.

The problem is that we are prone to act out of habit, unquestioningly. I see this in my coaching clients. They feel the pressure to keep moving forward everywhere. It’s difficult to admit our common human condition of thinking we know more than we do. The ego protects itself by gravitating toward feelings of certainty. In that state of mind we’re unlikely to ask questions.

Being comfortable with not knowing is the first part of being a good questioner. Asking naive questions without feeling self-conscious is not easy to do. A beginner’s mind is open to all possibilities while an expert’s is not.

Even if you don’t yet know “how,” it’s important to ask “why” and “what if” questions. Yet even when people do ask questions, they’re often relying on assumptions and biases.

“Every time you come up with a question, you should be wondering, What are the underlying assumptions of that question? Is there a different question I should be asking?” ~ Robert Burton, MD, On Being Certain

Ask “How”

The “how” stage tends to be a slow and difficult part of the creative process. It’s marked with failures which don’t always feel good or beneficial. To act on an idea, narrow down the possibilities and commit to finding a way to materialize it.

Sharing and feedback are a critical part of this stage. Fortunately, it’s easier now than ever to get prototypes made and reviewed. In the future, if 3-D printing becomes widely available and affordable, this might become even easier and faster.

A Culture of Inquiry

It’s happening already. We’re expected to quickly adapt to using new and unfamiliar tools every day. The technology is always changing and there are never clear instructions.

Like it or not, we are expected to adapt– now. The future is here. Most of us need to ask better questions and become better experimenters. If you’re uncomfortable asking questions, talk with a professional coach.

The best coaches, managers, consultants and therapists seem to agree: there is no substitute for self-questioning. The most important help an adviser can give is to suggest asking provocative questions, both of yourself and of others. It might be helpful to engage in “question-storming,” that is, brainstorming to generate better questions instead of ideas.

What do you think? How often are you willing to ask creative questions? I’d love to hear from you. I can be reached here or on LinkedIn.

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