Creative Questions: How to Ask Better Ones in a Brainstorm

Most brainstorms start with a problem and jump straight to solutions: "We don't have enough money" or "Nobody reads our newsletter." The group stares at the statement and waits for inspiration, which often never arrives, because a problem described this way works like a wall. Creative questions turn that wall into several doors, and each door tells your mind where to look.

The line above comes from Dr. Roger Firestien, who taught creativity at Buffalo State. In an excerpt from his book Create in a Flash, his advice is practical: before searching for ideas, write down at least fifteen creative questions that restate your problem.

Why creative questions come before ideas

The words you choose for a problem decide which ideas you can notice. "We don't have enough money" leaves only two moves: give up or complain. Now compare three different framings:

• How might we raise the money?
• How might we reduce the cost?
• How might we start without spending anything?

Each version opens its own field of possible answers. This reframing is a core step of Creative Problem Solving, the method Firestien teaches: restate the challenge as a question, then generate ideas for the strongest one.

A useful creative question usually has three features:

• it begins with "How might…" or "How to…", so it expects several possible answers;
• it describes what you want to achieve instead of what is wrong;
• it stays open enough for many answers and specific enough to act on.

How might we questions: one problem, fifteen doors

Firestien's main rule is quantity. Fifteen questions sounds like a lot, but according to him the whole exercise should take only five to ten minutes. The first few framings are obvious, and the interesting ones appear later, once the obvious ones are used up. Afterwards you choose the version that best describes the real obstacle and brainstorm solutions for that one.

Take a familiar complaint, "Our team meetings are boring", and restate it as four questions:

1. How might we make meetings shorter and more focused?
2. How might we cancel the meetings nobody actually needs?
3. How might we encourage quiet colleagues to speak first?
4. How might we discover what "boring" means to each person?

The last version describes a completely different problem than the first one. That is the real value of many brainstorming questions: you get different problems to solve instead of the same problem repeated four times.

The question burst: four minutes, no answers

Hal Gregersen of MIT Sloan describes a similar exercise in Better Brainstorming, published in Harvard Business Review in 2018. He calls it a question burst:

1. Describe your challenge briefly.
2. Set a timer for four minutes.
3. Write only questions, without answering them or explaining why you ask.
4. When the timer stops, read the list and mark the questions that intrigue you or make you slightly uncomfortable.

The rule against answering is the difficult part, because most people automatically respond to the first question they hear. Holding back keeps the list growing, and the uncomfortable entries often reveal an assumption you didn't know you had.

How to ask better questions

These moves work alone or with a group:

• Turn every complaint into "How might we…".
• Change one word at a time: "we" becomes "our customers", "raise" becomes "save", "money" becomes "time".
• Look for the need behind the problem: why does this matter to me?
• Borrow someone else's perspective: a critic, a new customer, a curious child.
• Keep every question you dislike, and cross it out later instead of immediately.

For questions about your own decisions rather than a group problem, see thinking with questions.

Creative questions in Ideation

In Ideation, roles reply with short thoughts, and some of them arrive as a question you hadn't asked yourself. That makes the app a convenient place to practice.

1. Write your topic as a question, for example "How might we make team meetings worth attending?"
2. Pick up to three roles. Critic stress-tests your ideas, Psychologist helps uncover what's beneath, and Politician answers a different question, which shows you another framing. Psychologist and Politician are PRO, but on your first board every role is open.
3. When a thought points to a better question, tap it. Its branch opens one level deeper, and the roles start thinking about that thought.
4. Add your own questions in the field at the bottom. They go straight to Favorites.
5. If the thoughts drift away from your situation, tap Context and describe your goal, your limits and what you've already tried. The roles use it from the next thoughts, so their questions become sharper.

A stuck problem rarely needs a better answer. It needs a better question, and the easiest way to find one is to write fifteen.