Seven practices to asking thoughtful, meaningful and impactful questions

As someone who has had an Asian upbringings and had grown up in Southeast Asia, I grew up with this belief that asking questions to your teachers, parents, supervisors or anyone in authority was a bad thing. In schools, we were taught to answer when teachers asked questions, and it was considered disrespectful to do the other way around. I remember one of my high school teachers telling me to my face that while I was a good student, I would be a much better student if I stopped asking too many questions in class.

When I migrated to Australia for my higher education, I was surprised to find that western countries encourages asking questions and this is considered participation and engagement. My university lecturers would often say that there is no such thing as a stupid question and would often start their answers with “That was a great question!”.

While I agree with the saying that there is no such thing as a stupid question, I have to say there are such things as good questions, thoughtful questions, meaningful questions and impactful questions.

In this article, I’d like to share seven practices that I apply before asking questions and they have helped me in coming up with good questions.

Have a purpose

Everyone has got an opinion and just stating your opinion without any purpose doesn’t make it a good question. A classic example is, “Why would you do X, I don’t think it’s a good idea (because I don’t agree with you!)”. Before asking a question, I usually think in my head, what is it that I would like to achieve from asking this question. Do I want an answer to a particular problem, do I want to uncover a blind spot, do I want to highlight an importance or do I want to get a better understanding or do I want to spark imagination and engagement? And if I don’t have any purpose then I don’t ask any question.

Give everyone else a chance

This is for extroverts who like to think out loud and ask questions as they pop up in their mind. While I think having such kind of people is good for bringing energy and excitement into the room, it’s not always ideal as extroverts tend to ask too many questions and end up taking the spotlight. Then when too many questions are asked by a single person, they seem less thoughtful because this is how people respond and perceive unconsciously. My advice for extroverts is to learn to think quietly or write things down first rather than speaking up whatever comes into your mind. Also note that this applies not only to group setting but also to one on one, because we all know how frustrating it can be not to get a word in during a conversation because the other party is talking non-stop and asking too many questions.

Have the courage to speak up

This is mainly for introverts who sometimes over-analyse their own questions and end up not speaking up because they are afraid of what other people might think. I know and I can relate to this very well being an introvert. It took me a long time to be with comfortable asking questions and to be ok with the fact that not everyone has to like what I ask as long as I have a good intention and purpose for asking questions.

Ask open ended questions

One of the things I have learned as I sit on the other side of the table as a result of being an interviewer is that how you ask questions influence the type of answers you receive. Being able to ask questions in such a way, usually open-ended and non-leading, enables the other party to think and respond without your unconscious influence. Examples of open-ended questions vs close-ended questions are:

  • How would you go about solving this issue? vs Will you be reaching out to X regarding this issue?
  • Tell me more about X. vs Tell me how you prefer X.
  • Would you mind sharing us your experience with X? vs What kind of problems have you got with X?
  • What are you most proud of about yourself and why? vs What are your strengths?
  • What are some areas for improvement? vs Do you think we are doing a good job?

Prepare ahead of time

If I knew in advance an agenda of a meeting, for example, career development planning, forecasting budget for the next quarter, meeting on resources allocation, etc, I usually think of questions that I would like to ask beforehand and think them through or even brainstorm them with someone else. I find that if I practice articulating my thoughts ahead of time, I feel more confident and better prepared when it is show time.

Observe and sense your environment

I’ve learned that I may have the best purpose and the best reason for asking a specific question, but if the question was asked at a wrong time or a wrong place, then I would probably not get the best response. It could even come across disrespectful or unrealistic. One of the characteristics of people with high emotional intelligence (EQ) is their ability to observe and sense environment and adjust themselves. This characteristics come in handy in asking questions too.

Be comfortable with silence

This is easily my favourite practice because it requires the least effort from my part but could possibly have the most impact. We all have been in situations where we asked questions and we didn’t get an immediate response, especially if they were meaningful questions. When this happens in the future, my advice is not to kill the silence by asking more questions or leading to a specific answer. As awkward as it may be, silence is good in this case because it means the other party is thinking. If there is no answer after a few minutes though I offer to let the other party get back to me later.

With these seven practices in mind, I hope that you will be able to appreciate good questions more and you will also be asking more good questions in the future.


Thank you for reading!

This article is a chapter from my upcoming book. Please subscribe to my mailing list if you’d like to be informed about when my book becomes available or be an early reviewer to receive a free advance copy of my book.