The Art of Asking Questions

Grasping the art of questioning can lead to impressive results; asking inappropriate questions usually closes off learning.

The attitude, mindset, pace, timing, environment, and context can all affect the impact of our questions.

While building my latest company, Growpo — software that enables legitimate imports and exports to move faster across international borders, I noticed that performance of my team members was dependent on the quality of the information being exchanged.

A question asked at the right time in the right manner with the right person is just as import as the content of the question itself.

Judging Versus Learning

Our mindset frames how we see the world. There are two types of mindsets that may reside in the questioner: learner and judger.

In the learner mindset, the questioner seeks to be responsive to life’s circumstances. Questions asked from the learning mindset:

  • What’s good or useful about this?
  • What possibilities does this open up?
  • What can we do about this?
  • How can we stay on track?
  • What can we learn from this?

The judger mindset, on the other hand, is reactive. Leaders with the judging mindset tend to focus on the past. Examples of judging questions:

  • Why is this a failure?
  • What’s wrong with you?
  • Whose fault is it?
  • Why can’t you get it right?

By consciously adopting a learning mindset, we can become more open to new possibilities and ask questions more effectively.


Good questions can become great questions when the science of inquiring is blended with the art of questioning.