Riddle Me This

by  John E. Smith  |  Leadership Coaching
Riddle Me This

The January Lead Change Group theme was critical questions.

Questions are widely touted as essential leadership and coaching tools. Some folks have written entire books, in-depth articles, and countless blog posts around the subject of questions.

Just do an Internet search using the keyword questions and you will have more reading material than remaining lifespan.

Common themes include classic types of questions, how and when to ask questions considering intent and context, and even how to respond to questions, all depending on your own goals for the interchange (knowledge sharing versus knowledge gathering and so on).

No question of the popularity of questions in our world, is there?

I have four distinct thoughts to share about the purpose of questions, whether we are asking questions within a personal relationship, a business context, or around societal directions. These might be helpful to consider as we prepare to ask our next question.


When we ask a question, and then listen to the answer, consider what has been said, and then respond, we are learning.

Questions help us learn something. We often ask a question because we want to know something we do not know. Sometimes we ask a question to test our assumed knowledge. We ask questions to move the ball down the field.

“How did you do that?” clearly opens the door for the other person to share their knowledge with us.

“Why didn’t you do instead?” is more testing in nature. Note, avoid testy questions, which is a whole other thing, and this type of question allows us to display what we already think we know about the issue, but still allows for continued learning.

When everyone is learning something they value, coming to consensus is easier than when they are not.


All good questions are examples of good leadership.

However, I am not talking about leadership in the traditional sense here, but leading, as in “leading a horse to water and then forcing him to drink” or however that folk saying goes.

Questions often point the way toward something. While one should never force a person to answer a question in a particular or desired way, how we ask has a lot to do with where the other person looks for their response.

“What other options have you considered?” is a good example of how to remind someone that more than one way to solve a problem or respond to a situation exists.

What do you think about?” is more pointed, and gently nudges the other person in a particular direction. Note the intentional use of the word “gently” here.

You are contributing to the shape of the discussion through leading participants with questions.


A good question contributes to the form and shape of the conversation in all contexts.

The structure of a discussion often has to be a delicate balancing act. We usually want our discussions to move relatively logically from point to point, from beginning to end, and be fairly equal in terms of contributions from all parties, but feel more relaxed and less rigid than strictly logical and highly organized.

Questions can change the direction of the overall discussion and even become a control mechanism which does not feel like a control mechanism.

“Are we ready to move on to Point B?” is an obvious example of how to change the subject and move down the agenda bullet points.

“Is this what we have agreed to, then?” followed by a short synopsis of what you think has been confirmed will also help end one discussion, opening the way for the next.

In both cases, the underlying message is “Let’s move on, folks” but when put into a question format, you are suggesting, rather than demanding or directing.

This creates a more amicable tone, which leads to the next point.

Setting The Tone

Finally, questions are always part of a conversation. Every element in a conversation is not a question, even if you are a coach or a cognitive therapist.

When asked in a collegial and non-confrontational manner, questions help create collaborative and amiable engagements with other people. When questions arise in a confrontational or hostile manner, they don’t, instead contributing to an me vs you or us vs them experience, which usually does not involve effective learning, positive leadership, or a very enjoyable atmosphere.

The use of we instead of you in your question when possible is an example of a small word which can mean a large difference in how the question is received.

Knowing yourself – motives, motivations, and morale – before engaging someone with a question is essential. We too often go into a discussion without preparation, which means we have given over control to our emotions and our desires. These are not alone adequate to create a positive discussion. Passion can be a great motivational driver, but it can also create a very energetic and frenetic atmosphere which may or may not serve your larger purposes.

Before you engage with another, you need to answer some self-knowledge questions. Here’s a sampling of what I try to ask myself before important connections are made:

  • Why am I doing this?
  • What do I need or expect to happen during our connection?
  • What is my specific and detailed current perception of the other person?
  • What are the beliefs, values, and biases I bring into the discussion?
  • What will set me off like a skyrocket?

Those are my thoughts about questions, so now I have a few questions for you:

  • What did I miss or misconstrue in the above?
  • What would you add to this discussion?
What is an experience with questioning, positive or negative, that you might share with us?
Photo Credit: Image Supplied by the Author

About The Author

Articles By john-smith
I enjoy helping people learn and grow through intentional, strategic, and social interventions. I coach, teach, train, facilitate, organize, write, speak, design, and lead at the intersection of leadership, learning, and human behavior. I am a CCE Board Certified Coach (BCC) with specializations in both Leadership/Business and Life/Personal coaching. My primary blog is The Strategic Learner on Wordpress.  »  View Profile

What People Are Saying

Mary C. Schaefer  |  31 Jan 2016  |  Reply

Hi John. What a great post prompting us to think about how we use questions!

A good question change change a person’s life, for the better.

Along the continuum toward the negative end is this experience. I was just telling someone yesterday about a type of question I call “Brian-ing” (I’ve changed the name of the “guilty” party.)

Brian-ing is when someone asks you a question and then answers it, or doesn’t give you the chance to answer. I knew someone who did this so frequently to me that I coined the term, “Brian-ing.” It can really stall a conversation. In this context it told me he really didn’t want my answer or to engage. Beware of “Brian-ing!”

Thanks again for the thought-provoking post, John!

John Smith  |  01 Feb 2016  |  Reply

Hi, Mary – thanks for your comments:)

I have met “Brian” or whoever he/she really is. I have actually worked with and for people like this and I agree it is one of those negative workplace behaviors that cause serious damage.

In my experience, Brianing often happens when someone thinks they are the smartest person in the room and sets out to prove it by setting up questions that they can then answer.

This is definitely not what I was talking about under Structuring, but might just be the evil twin of that idea.

As always, enjoy your thoughts and perceptions:)


Jane  |  01 Feb 2016  |  Reply

From someone who was born asking questions, I appreciate the framework you’ve designed for asking questions. Learning, Leading, Structuring, and Setting the Tone are all important aspects of question asking. I hadn’t thought about setting the tone but now that you mention it, we all do that in some way now, probably mindlessly. We should carefully consider tone. One of the greatest barriers to good questions is good listening. Listen first – and see the quality of your questions improve.

John Smith  |  01 Feb 2016  |  Reply

Hi, Jane – thanks for your comments:)

Yes, I would definitely agree that Setting The Tone is the most often missed aspect of communication. Not sure why, since we all clearly sense when the tone is off, but being proactive, while more difficult, is definitely a positive thing, in my opinion.

I had to smile at your very first sentence:). I believe that almost all of us are born as inquisitive learning machines. However, I also believe that our formal educational system and some of our societal expectations serve to stomp that curiosity right out of us.

Your comment about the importance of listening in all this is key. Absolutely essential.


Edie Patterson  |  05 Feb 2016  |  Reply

Great post-and reminded me, again, of something I learned in one of my college jobs.
I worked in the Government Depository section of the university library, which is where all the GPO (Gov’t Printing Office) are sent for reference and filing. This included UN documents, military training manuals, etc. People used this section of the library for all kinds of research.
What I learned is that if the researcher didn’t know how to frame the questions they had, the librarians had a much harder time finding the relevant documents or sections of the library. A good librarian who could help the researcher frame the question, or define more clearly what their research purpose was, was absolutely key to successful research. Many researchers had to learn how to ask the right questions in order to get where they wanted to go-but sometimes they didn’t know where that was! That learning has been a large part of my facilitation and nonprofit practice, and was a key part of my education at school.

John Smith  |  05 Feb 2016  |  Reply

Hi, Edie – thanks for your comment and observations:)

As a former librarian (PT as a student) and life-long researcher and haunter of libraries, I could not agree more with your point about knowing what and how to ask for help or direction. You have also clearly noted our responsibility as professional helpers to assist the person to form the question that will give them the information they seek.

This seems intuitive and simple, but in practice, it is often anything but clear on how to do this:).


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