How to Ask Questions That Generate Possibilities

Guest Post by Keith Webb

Originally published at 

Questions are not all equal. Some questions engage the listener, promote creativity, and generate possibilities. Other questions shut down creativity through the question’s pre-determined limited responses. I want to ask questions that generate creativity and possibilities, how about you?

Questions that Limit

First, let’s look at what limits creativity. When we ask a question that includes an answer, the listener must respond to that answer, often with a “yes” or “no.” This type of question doesn’t cause a lot of reflection because the options for response are extremely limited.

One reason we ask limiting questions is because we are stuck in our own perspective. We have ideas and when we form questions, those questions come out with our answers imbedded in them.

  1. Are you planning to borrow money to do that? (guessing the answer)
  2. Could Susan help you? (suggesting Susan)
  3. Do you learn from books or talking with people? (“or” questions give two answers)

Questions that Generate Possibilities

Ask questions that promote creativity and generate possibilities by asking more broadly about the topic. Begin your questions with the words: What, How, or Who. Compare these questions to the ones above:

  1. What are your plans to finance that?
  2. Who could help you?
  3. How do you prefer to learn new things?

These questions have unlimited possible answers. The listener is not merely saying “yes” or “no” to your idea. Questions with these words tend to produce more reflection and answers that are full sentences. Most important, they stimulate the creativity and generate possibilities for the listener.

There is some risk in doing this. The response to an open question can go in a hundred different directions. Asking open questions requires the coach to give up control of the response. But creativity and new possibilities only emerge when we move beyond what we know and explore what could be.

Question: What question have you heard or used lately that generated possibilities? You can leave a comment below: 

Keith Webb


Dr Keith Webb, PCC, is the founder and President of Creative Results Management, a global training organization focused on equipping Christian leaders. For 20 years, Keith lived in Japan, Indonesia, and Singapore. These experiences led him to question conventional leadership practices. In 2004, Keith created the COACH Model® and since then, a series of International Coach Federation (ICF) approved coaching training programs. In the revised and expanded edition of The COACH Model for Christian Leaders, Keith shares the process that he taught more than 10,000 leaders around the world use to solve problems, reach goals, and develop people. Keith blogs at


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