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How to Teach Your Tween to Ask Better Questions — So They Can Learn Independently

In today’s edition of Tween Talk:

This week’s big idea:

Thinking is just asking and answering questions. Better questions lead to independent learning — and true confidence.

─── ⋆⋅☆⋅⋆ ──

The Bridge from Last Week

Last week we talked about building connection as your foundation. But what happens when connection is solid and your tween still hits a wall? They sit there, staring at their math, finally muttering, “I don’t get it.” Now what do you do?

Here’s what I realized — they don’t know how to think about the problem. And here’s the insight that changed everything for me. Thinking IS asking and answering questions.

This week we’re talking about teaching your tween to ask better questions so they can become independent learners. Because if they can’t think things through, they can’t learn them independently.

The Thinking Skill Hiding in Plain Sight (And Why Most of Us Never Learned It)

I remember watching a seminar by Andrew Pudewa, the founder of the Institute for Excellence in Writing, where he said that thinking is simply asking and answering questions. And that was the first time someone had put into words something I had known and been doing for years. 

He was specifically talking about writing — how to get words on the page by asking yourself questions and essentially writing down the answers. But here’s the thing… if your ability to ask questions is weak, the output will also be weak.

And that’s what I noticed as my girls were in middle school. It’s easy to just ask simple questions you can get an easy answer to — these are googleable questions. They’ve been answered before. But what we want is to get to the point where your middle schooler can ask a question that requires the answers of other questions to close the loop.

Nic Peterson, a business mentor of mine, talks about keeping some loops open — not rushing to close them, but sitting with them for a while. Then your brain is always scouring your environment looking for the answer. You’re asking and answering more questions as you struggle to find the answer to close the loop.

And then one day, you’re like — Eureka! I’ve got it. And there’s a unique satisfaction to that.

But when your middle schooler is asking a question like “Which pages of math do I need to do?”, it’s an open loop you need to quickly close so they can continue with their work. Those simple questions aren’t what we’re talking about today.

How Question-Quality Reveals Thinking-Quality

There are different levels of questions that reveal different levels of thinking, and some you’ll use regularly, and some you’ll pull out when you seriously need to think things through in new ways. But they’re also indicative of critical thinking skills.

The most basic type of question is simply recall — “what’s 7 times 8?”

Then it moves up to comprehension questions. These check understanding, summarize or explain something. “How do I solve for X in this equation?”

Then we move up to application questions. That’s taking what you learned about solving for X and applying it to a different type of problem. 


That’s what I’m hoping you’ll do with what you’re learning in this article — you’ll ask yourself, “how can I help my tween ask better questions?”

Then you move up to analysis questions. You’ll look at patterns, relationships, cause/effect. Things like — when I modeled how to ask questions my child was able to ask a better question, but when we weren’t in “learning mode” they reverted back to simple recall questions.

Or you’re asking yourself things like, “How can I get my child to dig deeper in their questions without prompting? How can we develop those critical thinking skills so they are ‘just the way we think’? How can I get them to ask, ‘Why did this happen?’ rather than just blindly moving forward without thinking — you know, spark curiosity.”

And finally, the highest level of thinking is evaluation and synthesis. This is when we make judgements (and yes, you should have judgement). How can you create something new from your ideas? How can you connect ideas to come up with a solution? 

In math, this might look like figuring out multiple ways to solve the same problem or recognizing when a concept from one unit applies to another.

Why We Need to Focus on Right Questions, Not Just Right Answers

So, while yes, it is important to get to the right answer because that is our measure of competence, without asking the right questions they’ll be stuck. It’s not enough to memorize the way to get an answer.

Take Math for example — yes, it’s good to memorize the times tables, it makes it faster to do other math, but the truth is that some kids struggle to memorize math facts. 

So what if, instead of pounding that expectation, we took a step back and focused on asking better questions related to those math facts — on developing number sense, that mental flexibility to combine and play with numbers instead of straight memorization without understanding how they work.

I wish I had understood this sooner; it would have saved many tense times around the table.

So when your tween is sitting at the table, stuck on a math problem, what do you actually do to help them ask better questions? 

I’m glad you asked.

A Step-by-Step Method for Breaking Down “Impossible” Problems

Here’s how to know exactly what question to ask.

Step 1: Identify the constraint 

You need to identify the most immediate constraint — that’s the primary thing holding you back from achieving your goal. Think about the very next step you need to take to figure out whatever the problem is.

Step 2: Find what’s blocking you 

Then ask, what’s the one thing holding me back from taking that next step?

Step 3: Solve just that one thing 

And once you identify that, you know what problem you need to solve. And here’s the thing — you don’t need to solve the entire problem. You just need to solve the problem that’s holding you back from taking the very next step.That’s a more manageable problem to solve. But it requires thinking things through in a different way. 

You’re looking at the problem as a series of tiny problems instead of a giant roadblock. (Stay with me here, I promise this makes sense when you see it in action.)

It’s a different way of thinking, but it will help your tween ask the right questions and get to the answer they need — without you. And that’s the goal, right? Independent learning.

Example: That Bear of a Math Problem

Let me show you what this actually looks like when your kid has been staring at the same problem for twenty minutes.

Instead of your tween saying “I don’t get it” or “I can’t do this,” you’re going to walk them through finding the real question.

You ask them, what’s the #1 reason I can’t solve this math problem?

They say they don’t know how to solve for X. (That’s why they’ve been sitting there twirling their pencil.)

Okay, so what’s the first step I need to do to solve for X?

They don’t know. So where would they find that information? (This is where you can help them figure out where to look — maybe they need a cheat sheet… but that’s a topic for another day.)

They look it up. But wait — the explanation is confusing.

So you go back to the top. What’s the #1 reason I can’t understand this explanation about solving for X?

They realize they don’t actually know what a variable is.

So where can they find that out? They go find out. And now they understand what a variable is, which means they can understand that first step in solving for X. Which means they can solve the problem.

You can see it’s a whole thinking process.

So instead of them saying “I can’t do this! Show me what to do” and then you having to guess where they’re struggling, you can walk them through step by step to get to the root of the problem.

It will take a bit more effort. However, once you get the hang of it, it’s liberating. 

All of a sudden no problem seems insurmountable because you don’t have to solve the whole problem.

You just need to figure out the next step.

A Framework for Asking for Help That Actually Gets Them the Answer They Need

Okay, so they’ve figured out the constraint. Great! But they still need help. So how do they ask for it in a way that gets them the answer they actually need?

Here’s a framework for asking the question.

1. Identify what you’re trying to solve 

State the most immediate constraint clearly.

2. Share your source 

Let you know where they got the information they used to try to solve that problem.

3. Explain what they tried 

Tell you what they tried and what happened when they tried it.

4. Ask the specific question 

Finally, they ask for help in solving the problem.

But when they ask this way, they’ve already been thinking things through. They tried something, it didn’t work, and so they’re coming to you as a collaborative problem solver looking for another set of eyes on a problem they’ve identified, rather than just hoping you’ll rescue them.

It takes effort on their part and yours (you may not feel like going through the process) but, I guarantee that if you help your middle schooler work through problems using this method, over time, their thinking skills will improve. 

They’ll start to get better at asking questions that lead to the answers they actually need.

You won’t notice the change immediately, and it may feel like every time you walk them through the process it’s like it’s a new thing for them, but it’s worth the effort. 

You’ll have given them a powerful problem solving tool that will continue to improve as their brain develops. And when they hit the high school years they’ll be more prepared to handle the academic rigor with confidence.

Give Them Room to Think

But they can’t learn this skill if we rush them through every stuck moment. 

They need time to try, fail, rethink, and try again. 

And that’s why kids need some breathing room when they’re doing their work, time to think things through.

Already in my mind I can hear you say, “But Marina, if I give them more time to get things done they’ll just waste more time!” 

Honestly, I don’t think your tween wants to sit at the table staring at their math for hours. And I’m sure you don’t think that either! But it’s likely they are tired of feeling like they don’t know what they’re doing. (That gets old, fast!)

And when they ask for help, they aren’t getting the help they need. Because the question they ask isn’t the real question. 

So the answer you give couldn’t possibly answer their real question — because it’s highly likely that you’re guessing at what they’re asking. 

And that’s not your fault… as much as our kids think we’re mind readers, I know I certainly wasn’t.

I know sometimes my daughter would ask a question, and I’d think the question was bigger than it was. So I’d spend some time expounding and giving examples, etc. All she wanted was to verify the next step.

After she told me that, I started asking if she’d like the long version or just the facts. Not shockingly, 99% of the time she just wanted the short version that helped solve her most immediate constraint so she could move forward. Live and learn!

Once you teach them this constraint method, they’ll be able to identify their real question. And suddenly they’re not stuck anymore. They can keep going — on their own.

Why Tone and Attitude Matter Less Than You Think When Your Tween Is Learning to Question

Okay, so there’s something you need to know as you’re teaching your tween to ask better questions. And this is important.

Asking questions, finding out where your thinking is incorrect, is risky. 

Your tween is desperately trying to set themselves up as independent. They want to be autonomous and may feel like asking questions is for people that don’t know anything — and they want to appear like they know things. 

So that connection piece we talked about last week becomes even more important. It’s only when they feel safe and connected to you that they’ll have the courage to ask the harder questions.

When connected/supported, they risk more.

And that’s your job — to make it safe to ask imperfect questions. 

Sometimes it feels like you’ll need to be a mind reader. And they’ll ask one question and want an answer to another question.

Here’s what a great question sounds like:

“I’ve tried to solve for X in this equation but I got stuck. I looked at the example in the book and I think I’m supposed to subtract 5 from both sides first, but when I do that my answer doesn’t match the answer key. What step am I missing?”

That’s a great question because it’s not google-able. It clearly shows they’re thinking through the steps to finding an answer.  

When your tween starts asking questions this way, celebrate! 🥳

A Note About Tone

Now, their question may come out snarky — their tone may need some work. 

In fact, when they ask sarcastically it may push your buttons and you may be tempted to focus on how the question was asked, rather than focusing on the thinking breakthrough you just witnessed. I get it. I don’t like feeling disrespected either. But it may not be intentional disrespect. 

At this age, with their developing emotional intelligence, they may not have thought it was disrespectful at all — they likely didn’t even hear the tone.

I remember calling my daughters out on their tone and them saying they weren’t trying to be disrespectful and they couldn’t “hear” what tone I was talking about. For real.

It took a minute for me to believe that. I mean, how could you NOT hear the tone?! But, I chose to take their word for it and move on, and then when we weren’t in the middle of a somewhat stressful conversation we talked about some of those emotional intelligence things.

When you have connection, that helps as you guide them into saying things appropriately. They don’t yet have the emotional intelligence to always moderate their tone — it needs to be taught as well.

Next week, we’ll talk about how to help and when to help. But for now, focus on teaching your tween to ask better questions using this constraint method — because that’s what makes independent learning possible.

Try it this week and let me know how it goes.

~ Marina

P.S. If you’d like to talk through how to implement this with your middle schooler, I’m happy to get on a quick Zoom call to work it through with you. Check my calendar to find a time that works for you. (If you don’t see a time that works, let me know and we can figure something out.)

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