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Asking more Questions

| July 23, 2019

by Jim Bruce

– Upping your game

In last week’s Tuesday Reading, Questions: How many have you asked today, we argued that the practice of asking questions is more important than any one of the answers we may be given, as asking builds our knowledge, teaches us about people, engages others, communicates value, sets an example, and develops others.1 Judith Ross, writing in How to Ask Better Questions,2 reminds us that asking questions can help develop those whom we ask, provide yourself with fresh and powerful ideas, and reduce the burden you place on yourself to have all the answers.

This, then, leads us directly to the question, “How do I become better at asking questions?”, which is the subject of today’s Tuesday Reading.

Formulating good questions is hard work. As we are asking a question, we are exploring a space of “knowns” and “unknowns.” Former U.S. defense secretary Donald Rumsfeld put it this way: “There are known knowns; these are things we know we know. We also know there are known unknowns; that is to say that there are some things we do not know. But there are also unknown unknowns — the ones we don’t know we don’t know. And … it is the latter category that tend to be the difficult ones.”3 Sometimes the unknown can be daunting. However, as Clayton Christensen likes to observe, “Every answer has a question that retrieves it.”3 And, Elon Musk points out, “A lot of times the question is harder than the answer. … If you can properly phrase the question, then the answer is the easy part.”3

So, where do I begin if I want to ask better questions? The best advice I’ve found is to be willing to get curious about any and everything, and to make sure that you have regular “quiet times” on your calendar so that you can have ample uninterrupted time for doing some clear thinking about the issues before you. And, to have this alone-time, you may find it necessary to get away from your desk. Find an empty conference room at some distance from your office, find a quiet place in the library, take a walk outside, go sit in a park by yourself; the possibilities are there for the taking. All you have to do is discipline yourself to take advantage and create the opportunity.

Ross2 also tells us that our most effective and empowering questions create value in multiple ways. They can:

  • Create clarity. “Can you help me understand what just happened?”
  • Lead to better relationships. “How’s your work going?”
  • Encourage others to think analytically and critically. “What would be the consequences if we did what you suggest?”
  • Inspire others to reflect and look at things in new and different ways. “Why did this approach work?”
  • Encourage breakthrough thinking. “Can that be done in another way?”
  • Challenge assumptions. “What do you think will happen if you take the approach you suggest?”
  • Create ownership. “Given your experience, what do you suggest?”

Having this insight into questions, is helpful, and leads to wanting suggestions for actually creating questions that will help us do this? Here are ten helpful ones I found on the dummiesTM website:4


  1. Plan. Earlier I noted the importance of quiet time. Use that time to think through your objectives for the discussion you are going to have. What are your goals for the discussion? What questions do you need to ask to achieve your goals? A plan will help you keep the conversation on course.
  2. Know and understand your purpose. Every question you ask needs to help you achieve your goal for the conversation. Know what information you need and frame your questions accordingly.
  3. Make it an open conversation. Avoid yes-no questions, preferring instead to ask open-ended ones. Questions that focus on “how,” “what,” and “why” will provide more information and can initiate a helpful conversation.
  4. Ask your question in the listener’s “language.” Speak in terms from the listener’s frame of reference. For example, if it’s a technical issue, use the appropriate technical vocabulary. If what you’ve asked isn’t understood, try rephrasing.
  5. Use neutral wording. Don’t ask leading questions – e.g., “How do you like the new décor?” – as they are unproductive. Your conversation partner is biased to go along with your implied judgment that it is good.
  6. Follow general questions with ones that are more specific. Use the responses to your general questions to guide you to the more specific areas that need to be discussed.
  7. Ask one thing at a time. You’ll get better, more concrete information if you ask one question at a time. If you want to know more than one thing, ask more than one question. It’s much harder for those in the conversation with you to avoid a separate question than it is to avoid a part of a more complex single question.
  8. Ask only the essential questions. If you don’t really need the answer to a question, don’t ask it. Be respectful of everyone’s time.
  9. Don’t interrupt. Listen to the full answer to your question. If you have crafted a good question, you will want to hear the full answer.
  10. Transition naturally. Build off the answer in framing your next question, even if it represents a diversion from your planned approach. This will signal that you are really listening to the answer you are receiving, not just going mechanically down your list.

So, now it’s up to you. You’ve now seen the value that asking questions can bring and have a set of suggestions about how to use questions to elicit the information you need. I encourage you to make use of these approaches to formulating questions as you lead those around you in the coming week. I think that you’ll see a big difference. However, getting value from what you’ve read is really up to you.


Make it a great week for you and your team.  .  .  .  jim


Jim Bruce is a Senior Fellow and Executive Coach at MOR Associates.  He previously was Professor of Electrical Engineering, and Vice President for Information Systems and CIO at the Massachusetts Institute of Technology, Cambridge, MA.



  1. Ken Downer, The Power of Asking Questions, RapidStart Leadership.
  2. Judith Ross, How to Ask Better Questions, Harvard Business Review, May 2009.
  3. Hal Gregersen, Bursting the CEO Bubble, Harvard Business Review, March-April 2017.
  4. Ten Tips for Asking Good Questions, dummiesTM web publication.