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Rupert Eales-Whites in his book, “Ask the Right Question!” says, “The core reason for negative or unsatisfactory outcomes in conversations and relationships is the failure to ask the right question. We all fail in this regard, because we have never been taught the art and science of effective questioning.” This month I would like to share some thoughts on the…..

The Art of Asking the Right Questions

What makes a good question?

Is it really that hard to ask a question that will open up discussions, create learning and sharing, and result in productive communications? The truth is, most of us don’t know how to ask good questions, or when we do ask a really great question, it is by accident.

There are several ways to ask questions. Some people seem really good at it, while others use a random, what-ever-pops-into-head approach. Fifty percent of good communications is good listening. Asking the right questions must precede good listening. Good questions pave the way for good communications. We have all encountered problems with bosses and colleagues, and especially with spouses from asking the wrong question at the wrong time.

We scratch our heads and wonder what went wrong? After all, we were just asking, right? The problem is that we were raised by parents and teachers who asked the wrong questions for most of our lives. Parents ask their children questions designed to teach them something. Teachers also use questions that are rhetorical or Socratic, designed to make us think and come up with the right answer, as predetermined by them. There is usually only one right answer, the one they are looking for.

Here’s a clue: these people—parents and teachers—aren’t really asking questions. They are trying to tell us something. They do not ask questions to learn something, but to teach what they determine is important. We learn from parents and teachers the wrong way to ask questions in the adult world. What Real Questions Are Supposed to Do Real questions are designed to learn about the other person’s way of thinking, and to gather information.

A truly neutral question is rare. Most of us ask leading questions designed to influence others to our way of thinking, just like our parents and teachers do. Instead of gathering information about the other person’s perspective, our questions lead someone down a thinking path of our choice. One needs only to view TV courtroom dramas to see prime examples of leading questions.

When you ask leading questions, you must hold your own agenda in sight, and design your questions to end up with a predetermined answer. The person asking the question is focused on getting to this result, and therefore is not really listening to the responder with an open and receptive mind. While this can be an effective teaching method, it is not a way of developing true and meaningful communications, because the listening is cut off by predetermined goals on the part of one person.

Different Kinds of Questions

Managers overuse this leading style of questioning, and then wonder why they don’t fully understand the actions of employees. They don’t have a grasp on what is really going on, because they aren’t asking open questions designed for learning. People in relationships, including spouses, often fall into the “leading question” trap, in persistent attempts to influence the perspective of the other person. People communicate better when they start asking neutral questions to learn about the perspective of the other.

Some authors define questions as being empowering or disempowering. Empowering questions are positive ones, such as:

  • What works best for you?

  • What are you doing right?

  • What is your favorite part of this?

  • When are you most effective?

Disempowering questions are also called judging questions. They bring up negative feelings and focus on what is wrong:

  • Why did you do that?

  • What went wrong?

  • Who caused this?

  • How could this have happened?
Notice that these disempowering questions can appear to be neutral. They resemble information-gathering questions. It depends on the source, the context, and tone of voice. There is a fine-line between information-gathering where one is exploring causes in order to find solutions, and questions that judge and blame. It also depends on who is asking the questions, their position of authority, and their prior history of being judgmental and blaming.

In order to frame questions in a neutral, exploration context, it may be necessary to qualify questions with statements such as: Help me to understand this situation… I just want to clarify the sources of this problem so we can solve it… Without blaming anyone, can we identify where we went wrong here? Questions are clearly the way to create open discussions, deepen relationships, and create a learning environment necessary in any relationship, be it at work or at home. We all fall into the trap of trying to influence through our questions, because it is so ingrained in us from early childhood on. It is hard to ask truly neutral, non-leading questions without influencing.

Asking Coaching Questions

Here are some guidelines for creating a more coach-like approach in our communications and questions.When problem-solving with another person, remember these three kinds of questions designed for three different levels of interactions:

Single loop questions:

How can you fix this problem? What needs to be done differently? How can this be done better, faster, more efficiently?

Double loop questions:

Is this the right problem to fix? What else needs to be considered? Is there another way to get better results?

Triple loop questions:

What is your role in this, and how do you need to be in order for this to be solved? What shifts in your thinking and being need to happen?

Clearly there is much that goes into asking the right questions at the right time. There is a body of research designed around Appreciative Inquiry, in which people are taught the effectiveness of keeping discussions and questions positive. We live in a culture that readily diagnoses what is wrong and focuses on how to fix things, without adequately investigating what is right. Research shows that people learn better when reinforced positively rather than negatively, yet we continue to focus on what is wrong, gaps in performance, and areas for improvement. As anyone who has ever used a personal or executive coach will know, a trained professional coach can teach us about the art of asking the right questions at the right time. Ask your coach to practice with you on the art of asking better questions

Final Thoughts:

Many of you have downloaded my new e-book, “The Art of Leading People.” Thank you. If you would like to down load the book you can go to my website coachpinney.com and there is link at the top of the home page that will get you to the book. I have a couple of spots open on my coaching calendar, so if you know anyone that is looking for a coach, I would be happy to discuss coaching with them. Thanks for your continued support and your referrals..
Coach Jerry


The highest compliment you can give us is to refer your family and friends.

Jerry Pinney

For the last twenty-two years Jerry Pinney has been president of his own consulting firm. Currently he focuses his efforts on providing executive and personal coaching to persons who are interested in improving their quality of life and consulting to small and mid-sized companies and nonprofits. He is a facilitator for peer advisory groups with The Alternative Board and is a Certified One Page Planning Consultant. Jerry has over three decades of experience in the food industry, and possesses a unique perspective of customer service, marketing and strategic planning. In addition to overall general management qualifications, Jerry has proven expertise in operational planning and business development. His food industry career started at Jewel Food Stores followed by a long career with IGA, with their retailers, wholesalers and ten years as Vice President of Marketing. In addition Jerry has served as Vice President of Membership for the National Grocers Association, Sr. Vice President of Procurement for Shurfine International and Executive Manager of The Zenon Hansen Foundation.

Jerry has also served on a number of nonprofit boards including: President of the Volunteer Center of Northwest Suburban Chicago. He is currently a Project Manager for the Executive Service Corps of Chicago. Jerry’s ESC assignments have included coaching for several Executive Directors, and consulting on various Board Development projects and on a number of strategic planning projects.

Jerry Pinney & Associates
102 East 32nd Street
Chicago, IL,
phone: 312-842-4577,
fax: 312-842-4705

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