Questions for Deeper Thinking


—Bite-sized advice for better business writing—

Questions for
Deeper Thinking

“A wise man can learn more from a foolish question than a fool can learn from a wise answer.”

— Bruce Lee

Even foolish questions can lead to innovation.

While cellphone makers raced to add more buttons, Steve Jobs asked, “Why not have just one?” While other vacuum makers sought to invent better bags, someone asked, “Why not eliminate the bag altogether?”

Questions open up spaces in a topic. They drive deeper thinking by requiring us to reconsider something we thought was settled.

Any question can spur deeper thinking, but some questions open bigger spaces than others.

What questions drive deeper thinking?

The questions below range from shallow to deep. Notice how the answers grow more involved, and the thinking becomes more expansive as you go down the list.

Is? Am? Are? Was? Were?

These questions ask you to remember information. They open only a small space for thinking, often requiring just a yes or no.

Is the meeting at 3:00 p.m.?

Who? What? Where? When?

These questions ask you to understand information. They prompt you to put a detail in context.

Who should attend the meeting?


This question requires you to apply information. It requires you to make use of knowledge.

How will we resolve the budget crisis?


This question asks you to analyze causes and effects. It prompts you to consider the reasons behind a situation.

Why are third-quarter sales down and expenses up?

Would? Should? Could? May? Might?

These questions let you evaluate options. They help you make improvements, imagine solutions, and set goals.

Would a promotional that targets lost customers reverse this trend?

What if? Why not?

These questions let you create opportunities and innovations. They open a wide space for building something new.

What if we do a “refer a friend” promotional, giving coupon codes as rewards?

What research supports this?

American psychologist Benjamin Bloom first created his hierarchy of thinking skills in the 1950s, but a whole new generation of researchers updated it at the beginning of the 21st century.

Each level of Bloom’s Revised Taxonomy requires the levels above it. You can’t understand something you don’t remember. You can’t apply something you don’t understand, and so on.

  • Remembering information is the start of thinking, providing you the raw materials to work with.
  • Understanding something means knowing why it is important and where it fits.
  • Applying ideas means using them in a practical way to accomplish something.
  • Analyzing something means breaking it into parts, seeing how they relate and work together.
  • Evaluating a topic means deciding what works well and what could work better.
  • Creating something means innovating, building, writing, programming, growing, developing. . . .

Creating is the deepest level of thinking because it requires all other levels.

How can I use these questions?

As you work your way through a new project, also work your way down the list of questions.

  • Is? am? are? was? and were? help you remember the details of the project.
  • Who? what? where? and when? help you understand the project.
  • How? helps you apply your learning to the situation.
  • Why? lets you analyze the project and the situation.
  • Would? should? could? may? and might? let you evaluate possible solutions.
  • What if? and why not? help you create your solution.

Try It Out!

Think of a project that you are about to start. Answer the following questions about it.

  1. Is the project large or small?
  2. Who will be involved?
  3. What are the goals?
  4. Where will the work be done?
  5. When must it be done?
  6. How will you do it?
  7. Why is this project important?
  8. Should you make any course corrections?
  9. What if you exceeded every goal of this project?
  10. Why not create a plan that does so?

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