How to Ask Questions that Promote Creative Thinking and Problem Solving

Being creative and solving problems are important skills for any team, no matter the area or project. Getting those creative solutions can be difficult, though; it's not easy to help your team develop a skill that is not quantifiable or formulaic. The very nature of creativity and the demands of problem solving make both endeavors difficult to standardize.
Asking questions – lots of questions – is one way to help your team think more creatively and see more potential solutions. Asking the right questions will get even better results. Here are several questions you can adapt to use with your team.

1. What would you do if there were no risk in trying it?

Your people are smart. They know that risk is, well, risky. They know that creative solutions don't always work well for the first thirty or so iterations. They may want to be creative, but feel that their job security isn't worth losing just to be the “rockstar idea person” for this one project. So they dumb down their suggestions, going with the tried-and-true approaches rather than striking boldly into creative but very risky territory.

When you ask them to imagine solutions with the risk removed, you're telling them it's okay to get crazy in a theoretical wonderland. Encourage discussions here; you'll get quite a few unrealistic ideas, but out of those may spring something both creative and actionable. That's your gold nugget.

2. What's another way we could ______?

his is a question to spring after the discussion has been going for a while and the standard solutions presented. Keep asking for alternative after alternative; eventually, you'll find people willing to voice the ideas that didn't make the initial cut.

You have to be patient with this approach, not pushy. Most people do not respond well to pressure, and if they feel like you're tyrannizing a discussion that could have ended a long time ago, they'll shut down. Instead, appeal for different methods or approaches on specific aspects of the idea in play. Offer your own ideas--however outlandish--as well. The goal isn't to come up with a hundred doable ideas; it's to throw about a thousand ideas across the table, and find the few creative and doable gems in the pile.

3. What are the main obstacles to _____, and how will we overcome them?

For some reason, negative events and emotions stand out more than positive ones. Framing the need for creativity as an open-ended, fun-filled "let's create a solution!" time might turn off your more realistic or even cynical team members. But presenting obstacles, or better yet, asking for others to come up with them, will open the door for information and insight.

The next half of the question is when the creativity comes in; now that the obstacles are out there, turn your team's collective brain power to figuring out how to get past them. Try to come up with a five or ten item list of potential solutions for every single obstacle.

To come up with a cohesive approach for a set of obstacles, you and your team can review all the potential solutions and look for patterns or connections. There might be a few solutions that solve multiple problems. Or, in the midst of the discussion, those creative brains might see the pattern that exists and create a new comprehensive solution, or find a better way to connect the existing ideas.

All of these questions help your team to realize that it's not only okay, it's great to present ideas and solutions that might not work. The presenting is only the first step in the creative process; it's often in the subsequent discussions that you'll find the best creative ideas and innovative solutions. Asking questions helps your team keep moving that discussion forward, taking it deeper, diving into their reserves of creativity and breaking out of the security mindset.