How to teach a child to ask better questions

There's a particular kind of conversation I've had hundreds of times with my daughter (and with plenty of my students too), and it goes something like this.

She is stuck on a problem, a philosophical or a mathematical argument she can't untangle, a concept that won't click, and I ask her:

What question are you trying to answer?

Nine times out of ten, she’ll pause, and even twitch as if she’s slightly uncomfortable. Then she’ll say something like: "Ugh, why is this so confusing?!"

I mean, she’s a middle-schooler, kids at this age are not the most tempered creatures.

But in my decade-long teaching experience I’ve seen many of my freshmen and sophomore students react the same. They would even ask the same question: why is this so damn confusing?!

At first I thought this was a genuine question. But it took me some time to realize that it's actually a complaint with a question mark attached. The reason some students are stuck is almost never the problem itself, but the fact that they haven't yet found the right question to ask about it.

What they don’t know (and what took me years to figure out) is that asking the right question is a skill, and one that can actually be taught.

And unlike most academic skills, this one pays off immediately, in every subject, in every conversation, for the rest of a person’s life.

Let me share with you a few things I’ve learned along the way about how this skill can be transferred to a child.

What a bad question actually does

Most children ask questions constantly.

Spend an hour with a curious eight-year-old and you'll field dozens of them. Why this, why that, etc. Parents are often exhausted by the barrage. It feels like inquisition at times.

So the problem isn't that children don't ask questions. Instead, it's that most of the questions they ask, and most of the questions we teach them to ask, are the wrong kinds of questions.

What is a wrong kind of a question?

A wrong question is the one that has a hidden assumption baked into it.

For example, "Why am I bad at math?" assumes the child is bad at math. "Why does my teacher hate me?" assumes the teacher hates them. "Why is this boring?" assumes the thing is boring.

The problem with questions phrased like these is that they foreclose the inquiry even before it begins. When children ask like this they’re not really asking for information: they’re asking for confirmation.

This matters more than it might seem at first. When a child habitually asks bad questions they build a mental habit of looking for confirmation rather than understanding. That’s a serious thinking trap. It reveals that they're not trying to investigate the world; they're just narrating it.

And that narrative can be damaging. If left uncorrected, this habit will follow them straight into adulthood. No wonder we have so many adults trapped into fixed mindsets who can’t break through.

So, as parents and educators, we have a duty to teach out kids to ask better kinds of questions.

How do we do that?

What a good question does instead

First, we have to understand what does a good question do.

A good question opens something up. It reveals that the questioner genuinely doesn't know the answer, and the question, if composed well, is structured to find out the answer.

The difference is easier to feel than to define, so here are three pairs of questions, so you can see the difference. In each case, the first question is the kind children naturally reach for. The second is what a good question looks like instead.

"Why am I bad at math?" → "Which specific part of this math problem keeps going wrong?"

"Why does nothing ever work out for me?" → "What's actually different about the times things went wrong versus the times they went right?"

"Why is subject X so boring?" → "Is there a part of this I genuinely find interesting, even slightly?"

The second question in each pair does something the first one can't: it creates a path forward. It's possible to investigate, and thus possible to answer. And crucially, it leaves the possibility for the answer to surprise you, which is the whole point.

Why children default to bad questions

You might think children default to bad questions because they’re lazy or not intelligent enough.

But, the real reason is that that bad questions are cognitively easier. They confirm what the child already suspects and require no uncomfortable revision of their existing beliefs. "Why am I bad at math?" is satisfying in a strange way: it explains the difficulty without requiring the child to do anything about it.

If you look deep down in your soul, you’ll recognize this within you as well. Our children are not that different.

Good questions are harder because they're genuinely open. The famous legal philosopher, Joel Feinberg has a phrase I always liked: he thinks children should have an ‘open future’ ahead of them. That is both liberating, but also challenging. Good questions that open several possible answers in the future require the child to tolerate not knowing the answer before they've asked it. For most children (and most adults as well) that discomfort is the first obstacle. Psychologist Erich Fromm called it the ‘fear of freedom.’

The second obstacle is that nobody models it for them. Most classroom questions have known answers. The teacher asks, the student retrieves. If you have a child in public school, you know what I am talking about. Most curricula teach to the test, either a standardized one for a future (high-school or college) application, or a state mandated one.

Don’t get me wrong, sometimes that's a useful exercise in recall, but it teaches nothing about the kind of questioning that actually drives understanding.

How to teach it

The most effective thing a parent can do is change the questions they ask their child, before asking the child to change theirs.

First, instead of "How was school today?", which produces the same one-word answer every time, try "What's something that confused you today?" or "Did anything happen that you didn't expect?" These are genuinely open questions: they don't have a right answer, but they invite the child to actually think rather than just report.

Second, when a child makes a claim like "This is unfair," or "I'm terrible at this," suppress your parental instinct to either agree or correct (tbh, this is challenging, I have to remind myself all the time). Instead, it’s much better to ask: "What would make you think differently about that?" Ask this not as a challenge, but as genuine curiosity. Also, “What evidence would change your mind?” This is the question that, if practiced enough times, becomes internalized, and the child will continue phrasing their future questions this way.

Finally (and perhaps most importantly), when your child is stuck on something, resist giving the answer. Ask instead: "What question are you actually trying to answer right now?" Often, they won’t be able to say. But, the act of articulating the question will often be enough to unstuck the problem.

None of this requires a curriculum or a formal lesson. It just requires you to pay attention to the quality of the questions being asked, by yourself as much as by your child. It’s a lifelong practice, but one that will pay hefty intellectual dividends.

Where to go from here

The reason I am saying all of this to you is twofold.

First, questioning is not a standalone skill. It sits at the center of everything else a careful thinker does.

For instance, a child who can ask good questions about evidence will be harder to mislead, and will be less prone to confirmation bias. If your child learns that early in life, they’ll be better than most adults who never learned to do that systematically.

It will serve as the foundation for their intellectual progress.

Second, if you want to build this skill in a more structured way, with weekly lessons that develop questioning alongside pattern recognition, reasoning about evidence, and the other foundational thinking skills, you should check out the curriculum I made for my own daughter. I got frustrated with the gaps in her public school education, so I took things into my own hands. I designed an entire lesson plan that will take her all the way to college, and teach her elementary thinking skills no school would ever teach her.

After finishing it, I realized that I could make something bigger out of it, and share it with other parents who wish to teach their kids the same kinds of skills.

So, here we are. I invite you to check it out.

The first book in this curriculum is called Seeing Patterns, and it contains 52 weekly lessons for children aged 8–11. Each one ends with discussion questions designed to be genuinely open, and a thinking challenge that has no single right answer. The goal of the lessons isn't compliance, but the slow, deliberate development of a mind that knows how to ask.

You can find the book here, and read more about the full curriculum here. Other modules are in production.

Let me know if you’d like a sample lesson, or a free review copy of the book, I’d be happy to send.