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Critical Thinking

Questions That Matter

Questions That Matter

We ask questions of people and answer questions from others many times a day, but how much thought do we really give to what these questions should be, how and when they should be asked and which are the best ones to put given the circumstances. In summary we might say “what are the questions that really matter in our conversations with other people so that these at least are well put”.

The word “question” comes from the shorter word and concept of being on a “quest” or to be on a journey for something important. As a result, questions that matter need to avoid being short, complex, negatively slanted, put too quickly and in general with too little thought. Instead they need to be crafted slowly and with great care. In what follows are ten ways in which we might do this:

Take lots of time for thinking and reflection. Although it’s sometimes possible to ask questions in the moment (and many follow-up or probing questions happen this way) for the most part it’s better to take those extra few seconds, and even minutes if you have them available, to really think about what you want to ask. As a first step try waiting a minimum of 5 seconds before you ask someone an important question and use the thinking time to focus on exactly what you want to ask about.

Keep it simple. It’s tempting to ask a long and complicated, or multi-part question that will elicit lots of information all at once. However, this mostly leads to confusion and, even when it doesn’t you may find that the other person answers only part of your question. It’s therefore far better to keep your question plain and simple and without multiple parts to it.

Carefully craft the wording. Apart from keeping our questions short and simple it’s also important to keep the language plain and without jargon or terms that may be misunderstood or confusing. A few extra seconds taken here can therefore save lots of time and effort to clarify what you are getting at, that was probably achievable with the very first question, if your words had been well-chosen.

Be positive. To help people to be responsive and even open-up in their answers, positively framed questions do much better (as opposed to a negatively put or phrased one-like “Don’t you think that it’s a problem when…”). Positive questions are as future-focused and optimistic as it’s possible to be and show no signs of judgment about the issue that the question is seeking to deal with.

Be open. Being open involves asking a question in a straight-forward and honest way without any attempt to manipulate, use subterfuge or guide the respondent to a particular answer.

Be exploratory. Many of the best questions that really get to the heart of what matters are exploratory. Such questions expand a subject or ask a question in such a way as to let the other person add in more information as they see fit (and do not edit or exclude it because the question was so narrowly framed).

Be Energizing.  Questions that are asked with positive energy tend to get answers in a similar vein and the discussion that follows is likely to be richer and more “possibility centered”. This approach also helps to extend thinking in new directions.

Go deeper. Some questions, and especially closed ones, are not intended to go deep into an issue but for questions that matter, they should be ideally framed to go a little deeper into a subject and get to the heart of the issue being discussed. This may take a little practice and some follow up questions to your first one in order to carefully peel back any layers.

Keep things calm and listen well. There is very little point in asking questions, even if they have followed all of the above advice, if we don’t calmly listen to the responses they elicit from the other person. Some people are so busy creating their questions in their head that they forget to listen or only do so on a very limited basis so that they can ask a follow up question immediately. Try to listen for twice as long as you usually do and feel the difference.


While not all questions are significant, those that are important to you or to the person putting them to you deserve to be well put. The above list of ten guidelines will help both parties in a conversation that matters to one and/or both of them to achieve this.

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About Dr. Jon Warner

Dr. Jon Warner is a prolific author, management consultant and executive coach with over 25 years experience. He has an MBA and a PhD in Organizational Psychology. Jon can be reached at

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About the Editor and Primary Author

Jon Warner

Jon Warner is an executive coach and management consultant and in the past has been a CEO in three very different companies. Read more

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