I’ve been thinking a lot this week about asking good questions, trying to find the underlying quality that all good questions have in common. I think I found it.
The reason I’ve been thinking a lot about questions is that in conversation, it's often not enough to be a good listener. Because you need a tool to move a conversation forward, to make it a dialogue. Questions are that tool.
So what do all good questions have in common?
Good questions are those that are enjoyable to answer.
This has several implications:
First, it loosens up the concepts of giving and receiving. The good questions are the ones where both people gain something. The person asking gains knowledge, while the person being asked enjoys the process of answering. Both people gain a deepened relationship.
Second, for questions to be enjoyable, they cannot be “boring”. This means that they must come from a place of genuine curiosity on the part of the questioner, while inspiring curiosity on the part of the answerer. A good question makes the answerer curious about their own response, and thus they start to listen to themselves.
Third, this curiosity about their own answer requires the answerer to think. This is what ultimately makes the question enjoyable – exploring and witnessing one’s own thinking together with another person to arrive at novel insights is deeply pleasurable.
There are a few ways to ask questions that I personally enjoy a lot.
One way is to ask questions that look at the topic from a different angle. You can do this by playing devil’s advocate, i.e. by looking at things from the opposite angle. An example might be “What would a critic say?” or “What would a wise person do?”
Another way is to question the underlying assumptions. When we solve problems, we usually presume a lot, thinking about implications rather than premises.
So by asking questions that focus on assumptions, you can help the other person check their thinking against reality. Examples might be “What would this look like if it were easy?” or “Is this the only way to solve this?”
And then there are questions that challenge the boundaries of your thinking by being absurd. We often think in similar patterns because of our beliefs. To break out of them, ask this kind of question.
For example, imagine someone was struggling with time management. You could ask, “How would you live your life if each day was only 12 hours long?” Or if someone was struggling financially, you might ask something like “What would you do if you only had $100 a month?” While those questions probably don’t apply to your specific situation, their answers might do. Thinking about them will help you gain new insights into your current situation.
None of these questions are “normal” – they are quirky and novel, they make you think in ways that you haven’t thought before. Your standard way of thinking doesn’t work. This makes answering them enjoyable because you start listening to yourself.
So both from the perspective of the person asking the questions, but even more from the perspective of the person answering it, you could say:
Good questions make you curious. Curiosity makes you listen.