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Want to Run a Better Brainstorming Session? Start with Better Questions.

A 2015 review of group brainstorming in the Harvard Business Review provided a scathing review of the common practice for businesses seeking to develop new ideas and discover solutions to existing problems.

In a critique of the father of brainstorming, Alex Osborn, authors claimed that “a meta-analytic review of over 800 teams indicated that individuals are more likely to generate a higher number of original ideas when they don’t interact with others.”

Former CNN anchor, White House correspondent, and Washington bureau chief Frank Sesno believes a lack of solitude may not be to blame for brainstorming’s bad rap.

According to Sesno, “we solve mysteries and we imagine new ways of doing things” by asking the right questions. “Smart questions make smarter people,” Sesno wrote in his book, Ask More. “But the fact is, most of us don’t really understand how questions work—or how to make them work for us. In school we study math and science, literature and history. At work we learn about outcomes and metrics, profit and loss. But never do we study how to ask questions strategically, how to listen actively, or how to use questions as a powerful tool toward accomplishing what we really want to achieve.”

The rest of this article is excerpted from a part of Sesno’s book that tackles creativity questions, the kind of inquiries that Sesno says can elevate a brainstorming session from the bane of your company’s existence to the reason for its existence.

brainstorming session

Is it possible to run better brainstorming sessions?

Questions—asked the right way, under the right circumstances— can help you achieve both short-term and lifelong goals.

Creativity questions, in particular, invite us to pull out the paintbrush, throw away the coloring book and think differently. They prompt our imaginations. They ask us to get out of the way, break rules of convention, and exceed the bounds of the possible. They encourage us to rally to greatness or peer into the future, to see a new world. They invite us to daydream.

Creativity questions may not hand you the next $50 billion business, but they will help you put together the best brainstorming session you’ve ever imagined. They will help you bring divergent viewpoints together and think about new ways to address a problem in your business, community, or country.

Creative questions can become a collaborative quest for answers.

What are creativity questions?

Questions that drive creative thinking are out-there questions. They are big and bold. They ask people to transport themselves to a different time and place and state of mind. They open the door to aspiration and disruption. They challenge the status quo. They reframe issues around visionary, maybe even revolutionary, ideas. You find inspiration in these fun questions because they invite fresh and original thinking. But you may also feel uneasy when they challenge conventional wisdom and the world you know. Whether you’re trying to invent the next big thing, make a crazy video to sell cars, or write the next inspiring chapter in your life, this line of questioning can help you hatch ambitious new ideas and bring people along for the ride to collaborate and create alongside you. Creativity questions ask you to pretend as they connect you to an imagined reality, where horizons are brighter and where limitations are lifted. They are questions that suggest everything is possible.

Why your brainstorming sessions need creativity questions

Creative questioning asks people to close their eyes and imagine. It welcomes crazy ideas, shrugs off the obvious, and seeks alternatives. Creative questioning asks fellow travelers to:

  • Set sights unreasonably high. Ask more of yourself and others without being limited by the laws of gravity. There will be plenty of time to come back to earth later. If you don’t aim high, you will never go into orbit.
  • Try a little time travel. Creative thinking is all about the future, so go there. Put your questions in the future tense and ask people to transport themselves there with you.
  • Invoke imagined reality. Role-play. You’re living in that new world, workplace, or community. What’s it like? Look up, down, 360 degrees around. What do you see? What do you think? What’s next?
  • Embrace disruption. Questions that drive creativity involve disruptive thinking that can be unsettling, uncomfortable, and sometimes downright subversive. That’s how we change the world.
Ask question concept. Question mark on speech bubbles, top view

Types of Creativity Questions

Creativity questions encourage people to think about things that go beyond the familiar. They encourage originality and risk-taking. They ask people to consider new ideas and imagine new scenarios. They put us in the future tense. They push boundaries. Creativity questions ask people to imagine ambitiously and think independently.

The Dream: What would you change? What if there were no limits? What is your dream? These are opening questions that grant license and unleash the imagination. You are asking people to put convention to the side, to set their sights high and try something new or experiment. These questions inspire people to think big, over the horizon to imagine new approaches, new definitions. They are the questions that frame the challenge, set the bar, and loosen the rules.

The Frame: What’s the next Big Thing? How can we eliminate poverty? What will it take to beat cancer? What’s the unexpected twist in the story? Frame your question to inspire and to invoke the future. Ask people to imagine a different and better place. Make the questions inspirational, to shift our gaze from the weeds to the sky.

Role-Playing: What if you were CEO? What would you do? What if you were the director making the movie? What would Jeff Bezos think about this situation? Ask your collaborators to try on another pair of shoes—the shoes of the decision maker. Ask them to assume responsibility. Your question puts them in another place. Now they are invested, thinking in a different context and imagining at another level.

Your Sunglasses: When should you take them off? You can direct the action and tell people precisely when to take off their sunglasses or you can ask people to invest themselves in the decision and think about what they are doing, why and to what effect? Invite them to be part of the creative process instead of just handing them a script. These questions challenge people to take ownership of the script and the creative process.

Time Travel: You succeeded. You’re in the future. What are you doing? What’s it like? What do you see? Skip past the particulars, the details, and the distractions. Forget the fear and the can’t-do white noise. Pretend money doesn’t exist. Ask people to boldly go where no one has gone before: the future. Ask them to look around and try it on. Then look in the rearview mirror to see how you got there and what it took.

The Superhero: What would you do if you knew you could not fail? That’s Gavin Newsom’s question. Ask it to help people embrace risk and understand that fear of failure should not stand in the way of brainstorming, big ideas, and worthy goals.

How businesses use creativity questions in brainstorming sessions

Creativity questions have an almost magical capacity to transport people to a different time, place, or perspective. They help us get to that imagined reality.

Asking people to play a role and answer a series of questions or a challenge catalyzes creative thought and innovation.

The consulting firm McKinsey & Company examined the best ways that businesses could use insights from neuroscience to unleash creativity and innovative ideas in their employees. McKinsey cited the work of neuroscientist Gregory Berns from Emory University, who found that creativity requires “bombarding” our brains with things that are new, unfamiliar, and different.

The McKinsey authors stated, “only by forcing our brains to recategorize information and move beyond our habitual thinking patterns can we begin to imagine truly novel alternatives.”

They provided some sample questions that businesses could use in a brainstorming session, asking what the best in the business would do in their shoes, drawing comparisons that most closely applied to their own challenges.

After all, creativity questions should be aspirational.

  • How would Google manage our data?
  • How might Disney engage with our consumers?
  • How could Southwest Airlines cut our costs?
  • How would Zara redesign our supply chain?

Pushing people out of their “habitual thinking patterns” is an exercise anyone can do.

Imagine that your daughter just won a full-freight scholarship to any school in the world.

Ask her:

  • Where would she go?
  • What would she study?
  • What opportunities would she have?

Or imagine you were named CEO of your company.

  • What would be the first things you would do to improve morale and performance?

Role-playing puts people in an imaginary place and asks them to play their part. The exercise works because, often without realizing it, players combine imagination with intellect and get into the game. They think in a hypothetical space and craft their responses to keep up with a storyline they cannot control or predict.

Your Brainstorming Sessions Will Benefit from Better Questions

We learn, connect, observe, and invent through the questions we ask. We push boundaries and we discover secrets. We solve mysteries and we imagine new ways of doing things. We ponder our purpose and we set our sights. We hold people accountable. We live generously, to paraphrase John F. Kennedy, by asking not what others can do for us, but what we can do for them. Curiosity opens our minds and captivates our imaginations.

Want to read more? Get the book!

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Frank Sesno

Frank Sesno is a former CNN anchor, White House correspondent, and Washington bureau chief, and is now director of the School of Media and Public Affairs at The George Washington University. He has interviewed dozens of world leaders, including five U.S. presidents, and is the creator of Planet Forward, an innovative forum seeking solutions to some of the world's toughest challenges.

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