How to ask deeper and more meaningful questions to gain greater understanding

How to ask deeper and more meaningful questions to gain greater understanding

How to ask deeper and more meaningful questions to gain greater understanding

An earlier blog article focused on the four levels of listening. This blog provides help, advice and insight on how to ask even better questions. This will help you gain empathy and also get you to a place where you can help others, through better understanding. This is essential when providing feedback and coaching.
Most of use recognise the power of asking open questions i.e. those that normally start with who, what, why, where, when and how. These questions usually open up conversations, inviting others to provide information, context, explanation and so on.
Closed questions are those that prompt ‘yes’ or ‘no’ answers. These are useful to clarify points and check understanding. When combined with open questions you can follow a pattern of enquiry that can explore thoughts, fact and feelings.
Hypothetical questions are useful to explore future scenarios and the potential consequences of taking particular actions. Again, these types of questions have their uses when coaching others to improve performance and solve problems that may arise. 
So these types of questions are ones that you may be familiar with. But how do you use questions to take understanding to a deeper level?

Consider this approach:

Level 1: Data collection
This level is all about gathering information. The open questions of who, what, why where, when and how or closed questions will definitely help here. For example, questions such as:

  • How are things? (open question)
  • Have you done this? (closed question)

However, unless supplementary questions are asked then the understanding may stop at a superficial level. Sometimes understanding the facts is not enough and a deeper level of enquiry is required. Probing to the next level will help.

Level 2: Discovering meaning and/or interest
This level of questioning takes a deeper dive, looking to discover what’s behind the responses shared at Level 1. Asking questions at this deeper level requires the use of open questions such as:

  • What do you think about this?
  • How do you feel about that?
  • What are the implications of what you did?
  • How did you come to that conclusion?

Interestingly our habits and unconscious bias can influence how we choose these types of questions. For example, the Myers Briggs Type Indicator (MBTI), SDI 2.0 and Belbin Team Roles can help us to understand habits and patterns of thinking, offering us greater choice and flexibility in the types of questions we can ask others.

Level 3: Understanding, challenging and/or affirming attitudes, values and/or beliefs
This level of questioning enables both you and the person that you are questioning to understand those core values and beliefs that so often drive behaviour. Here are some examples which I have found very useful in a variety of workplace and personal situations:

  • Why is this important to you?
  • What has made you feel this way?
  • How does this concern you?
  • What to you believe made you take this approach?
  • How has this been helpful for you?

When asking these questions be prepared for long silences as you may have asked a question that has never been considered before. Give the other person time and space to think through their response.

Also, be prepared to repeat the question. This will help you probe deeper. Of course, you need to pay attention to how the conversation is going as this technique of probing should never become an interrogation. Always check your own intention behind asking the questions – self-gratification is not a reason for delving deeper with your questioning.


As always, being an effective leader is situational. However, being a situational leader requires the use of appropriate interpersonal skills, and questioning is definitely one of these.
When it’s appropriate, make and take time to take a deeper dive into why the other person has done what they have done. We often judge ourselves by our intentions but others by their actions. Asking the right questions will help.
Paul Beesley
Director & senior consultant, Beyond Theory
29 January 2024

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