Get into the habit of asking better questions.

The art of questioning is straightforwardly easy — unless we have been living in a society where everyone has an answer and we ask few questions. Then, suddenly, it is not so straightforward.

At first we might bring up a subject and ask a question about it. We can also ask a question about a subject someone else has provided and begin there. Especially when we are communicating in written form, it can be more confusing than speech — but it is also more easily understood in writing, because the words stay still long enough to be inspected.

The habit we have lost

We are so accustomed to laying out our own point of view online, and then defending that view, that we are simply out of the habit of asking many questions.

We think — just ask questions? that is easy — and get trapped in a useless back-and-forth that goes nowhere. A question is not automatically Socratic. A question can be a trap, a taunt, or a way to make someone else do the work while we watch.

Great questions are important, and they encourage better communication. Questions meant to challenge someone unfairly do not lead to better communication. "Gotcha" questions, the kind designed to lay bare a person's weaknesses, have their place — but they are not generally helpful if the goal is mutual understanding.

The midwife of ideas

Socrates, the Greek philosopher whose mother had been a midwife, considered himself, by using a particular mode of questioning, to be a midwife of ideas. The aim was not to install knowledge from the outside, but to bring forth knowledge from the person being questioned.

That is a different posture from the one we usually adopt online. It is slower. It does not win arguments. It does, however, produce thinking that a person can use after the conversation ends.

The child's "why, but why?"

We start out in life asking questions. Anyone who has been driven to distraction by the insistent questions of a two-year-old knows how powerful a small person asking, "why, but why?" can become.

Watch: the relentless "why" of a small child

Why does the unending questioning of a child drive us so easily to distraction? Because by the time we are old enough to be tending such a child, we are generally quite certain about everything, and a long series of questions is irritating. The child has not yet learned that certainty is a social credential. We have.

How can more questions make us wiser?

That is the most important question. And the next one is just as urgent: how do we ask these questions without making everyone angry and uncomfortable?

We are not Socrates, and most of us have no desire to get caught in a long tutorial about Socratic methods. Dry discourse about uninteresting subjects is precisely what we are seeking to avoid.

A way of avoiding dry discourse is to throw out a question that is on everyone's mind, and about which everyone has already formed an opinion. The goal is not to point out where someone might be wrong. The goal is to proceed to ask better questions.

A working definition

A better question is one that moves the goal posts of human understanding forward — even just a little. It does not have to produce a final answer. It has to make the next answer better than the last one.

This is the discipline: ask in such a way that the other person can keep their dignity while reconsidering their certainty. Ask so that you yourself could also be moved. If only one side is expected to change, it is not a question. It is an inquisition with a polite face.

One question to begin with

Here is a question to take into the next conversation, the next post, the next argument:

What is one question you have been avoiding because you already think you know the answer?

If you ask it honestly — of yourself first — you will find that the habit of better questions begins not with technique, but with a willingness to be a little less certain than you were yesterday.