The Lost Art of Asking Meaningful Questions

July 15th, 2019  |  Laurie Hawkins

If asking good questions is critical, why don’t most of us spend more of our time and energy on discovering and framing them? One reason may be that much of our culture and society in particular, focuses on having the “right answer” rather than discovering the right question. Our educational system focuses more on memorization and right answers than on the art of seeking new possibilities. We are rarely asked to discover compelling questions, nor are we taught why we should ask such questions in the first place. Quizzes, examinations, and aptitude tests all reinforce the value of correct answers. Is it any wonder that most of us are focused on providing great answers instead of asking great questions?

In conversation with others, people are always responding with “so what” in their own minds. When you focus on telling people things, they are always justifying the investment of their time with you. Instead, when you are asking questions, they are focused on the interaction with you. What a powerful reason to shift to being curious!

There are many ways to build the habit of shifting to being curious. I have found a few ways to incorporate questions in a meaningful way. One of those ways is by leveraging the feel-think-opinion strategy.

Three Questions That Allow You to Connect on a Deeper Level

Feel Questions: Find ways to incorporate “feel” questions into your conversations. When you ask someone how they feel about something, it forces them to emotionally connect with their core values and emotions on that subject. This immediately allows you to experience a deeper level of understanding about the other person and their desires.

Think Questions: When you ask someone what they “think” about a certain idea or topic, then people must dig into their minds for an answer. It becomes personal as you are asking for their specific ideas. This allows you to uncover their specific thoughts on any area of interest.

Opinion Questions: Asking opinion questions influence people to provide both their emotional and logical answer. It connects the heart and the head in a response. These questions are very personal to those answering as you are asking for them to specifically answer about what they think and feel on a topic. These can elevate any conversation and open it up to new areas of discovery.

The other powerful questioning strategy is leveraging the “three deep” investigation method. This requires you to listen intently to the person you are speaking to so you can intuitively go deeper into their original answer. It’s where you ask them to “tell you more” about the subject you are discussing. When they give you an original answer, you want to stay on that theme and just continue to learn more about the subject. You keep going at least three deep into that area.

You can use statements like:
→ Tell me more…
→ How did that impact you?
→ What did you learn from that experience?

The more you dig into a theme or subject, the closer you will get to the true core of that area. You will uncover more about the subject and have people share at a deeper, more meaningful level.


What has kept you stuck from asking questions? How could you step into becoming more curious? What are some outcomes you would experience when you made this shift? What action will you begin today to practice the art of questions and connection?