Asking the RIGHT questions


 One good question can give rise to several layers of answers, can inspire decades-long searches for solutions, can generate whole new fields of inquiry, and can prompt changes in entrenched thinking (Stuart Firestein)

Asking question is the cornerstone to improving your critical thinking

Here is the situation: You have a problem. You need to see your teacher/mentor/ advisor/ coach/ supervisor to work out the solutions. When you request the meeting, you are fully aware that you will come with questions. 

You might find yourself in one of these situations:

  1. I have my problems detailed, but I am not sure which questions to ask
  2. I have tons of questions to ask my mentor and hope I have enough time to ask them all
  3. I have a specific inquiry plan for the upcoming conversation

In either of these situations, you can definitely make your meeting time for effective and fruitful by delving a bit more into the science/art of inquiry. This note is far from being the model guideline for all inquiries, but a source of reference and inspiration to facilitate your preparation for an upcoming meeting and any other time in your life when you need to raise a question, and even better a good question.

1. Any helpful models of inquiry out there?

a/ Creative Problem-solving process (by Warren Berger) = Great for when you would like to understand the design thinking of your advisor when he/she handled a problem that is similar to yours. The essence of this questioning framework is the coherence between the questions to reveal the process of problem-solving. Process-oriented approach is more fulfilling for one's personal development in the long run compared to a product-oriented one. 

  • 1st Q: Why
  • 2nd Q: What if
  • 3rd Q: How

b/ The Golden circle (by Simon Sinek) = A standard set of questions to understand a matter, just make sure you prioritise “Why?”. This set of question mainly urge for actions by clarifying where you want to head to. An easy analogy of this approach is like when you plan your summer vacation. You ought to check the destination prior to all other prepping steps, such as flight and hotel booking or packing, right? 


Also, once your "why" is clear, you can always return for re-orientation in the event of getting lost as you proceed your tasks. At the back of mind, think about why you began all of these. 

c/ The Comprehensive structures of inquiry (by Socrates)

The unexamined life is not worth living at all (Socrates)

The video at the beginning of this post is a comprehensible introduction to Socratic questions. Please watch it if you are yet familiar with Socrates. 

Grateful to James Bownman for this infographic on 6 types of Socratic Questions.


If Socrates were to be alive, he would definitely earn the title “The Man with the most questions in his mind” haha He approached in a rather satirical way, which prompted to ask endless questions. Although he had tons of questions, he actually has a logical model to questioning types. Here born the Socratic questioning technique. 

2. So, what kinds of questions to ask then?

Of course, you don’t have to ask all of these questions in one meeting. These questions are here for your reference. One important thing to notice is each question triggers different level of cognitive load from the recipient. Let’s use Bloom taxonomy for reference of cognitive development.


For example, “what is....?” only requires the lowest level of cognitive load, which nowadays is the job of Google rather than any specific human.

“Why...?” or “Are there any alternatives?” requires at Analytical and Evaluative skills in the answer, so asking the compatible questions is a token of respect from you to your advisor

3. Think before you ask, even better is to write your questions down before the meeting

Always the beautiful answer who asks a more beautiful question (E.E.Cummings)

Even when you think you know what to ask, it would be easier to check your wordings if you write the question down in advance. We might instinctively insert our assumptions in the questions, so we might not leave enough room for the recipients their points to the fullest extent.

Eg. HOW MIGHT WE .....?

  • How = Assume there is a solution to the focused issue
  • might = The solution/ plan might not work
  • we = you and I do this together

A short list of words to watch out for:

  • Pronouns: Who do you really want to ask about?
  • Hedging phrases eg. might/ likely/ possibly: How certain are you with the topic?
  • Question words: What is the purpose of this question?
  • Tonic words: Think of the recipients of your questions, what kinds of language particularly sing to their ears?

Asking a question might seem effortless, but asking the right question to a person is actually effortful. All the efforts will pay off, so don't hesitate to invest some brain cells in finding and forming the right questions.

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