Thinking in English Episode - 379. Do You Know How to Ask Great Questions?

Do you know how to ask great questions?

A few years ago, back in 2022, I released an episode called How to Ask Better Questions in English. And todayโ€™s episode is an update to that original one.

The core idea is the same, because itโ€™s still important, but a lot has changed since then. Iโ€™ve changed as a podcaster and an educator, and I think English learnersโ€™ needs have changed too. In fact, the way we use English in 2026 is very different from how we used it just a few years ago.

We now spend more time in online meetings, working with international teams, and communicating through messages, emails, and AI tools. In this kind of world, the ability to ask good questions matters more than ever.

Most people know how to ask questions, but very few people know how to ask good questions. And learning how to do that can change your English, your conversations, and the opportunities you have.

Today, we will look at different types of question, what makes a good question, and Iโ€™ll give you a lot of useful advice!

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How to Ask AMAZING Questions!

In 2026, I think “question asking,” or [00:02:00] “the ability to ask good questions”, is becoming a vital life skill.

Many people work in global teams. Maybe you sit in online meetings with people you’ve never met in person. Or maybe you build professional or personal relationships through messages, emails, and short conversations on Instagram.

In all of these situations, asking the right question at the right moment can make a huge difference.

In a global workplace, for example, good questions help you understand expectations, avoid misunderstandings, and show that you’re engaged. And this is especially important if English isn’t your first language.

Online, in meetings or in online classes or online calls with your friends, it’s easy to stay silent or get ignored, so a clear [00:03:00] and thoughtful question can really help you understand better and get people to understand you better.

This is also true in the age of AI. Whether you are using ChatGPT, or Gemini or Claude or whatever else there is out there right now, the quality of what you get from the AI depends almost entirely on the quality of what you ask. Vague questions lead to vague answers; clear questions lead to useful ones.

The skill here is exactly the same. You need to know what you want and you need to express it clearly.

And this isn’t just my opinion. Research consistently shows that people who ask more questions in conversations are seen as more engaged, more intelligent, and more likable. They also tend to learn more.

Asking good questions [00:04:00] demonstrates curiosity, confidence, and respect. These are all qualities that matter in professional and personal relationships.

We live in a world full of information. Answers are everywhere. You can Google almost anything, or AI can generate explanations in seconds.

But what really matters now, is whether you are asking the “right” questions to get the “right” answers. Because if you’re not asking good questions, the information that you get from Google or from Gemini may be incorrect or not exactly what you are hoping for.

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Common Question Mistakes

Most people are not very good at asking questions.

This isn’t an English learner problem. Native speakers are just as bad, maybe worse at asking questions. I’ve probably made mistakes, myself, asking questions.

[00:05:00] I’ve sat in university lectures and business meetings where someone asks a question, and halfway through that question, everyone in the room is already confused or bored or frustrated.

One common problem is rambling. Rambling questions. People talk for so long that by the time they finish, it’s no longer clear what they’re actually asking.

Sometimes the question includes background information that isn’t necessary. Sometimes it turns into a speech. And sometimes it never really becomes a question at all.

Another issue is questions designed to show intelligence rather than get an answer. I saw this constantly as a student at university. Someone would ask a long, complex question filled with academic language, because they wanted to sound smart.

And the result was usually the [00:06:00] same. The professor had to ask them to clarify, or the professor answered a completely different question because they were confused.

Then there are questions with hidden opinions. These are questions that already contain judgment or an assumption. They are biased. They don’t really want an answer. They want agreement, and if the other person disagrees, the conversation can quickly become awkward or defensive.

This is why question quality matters. A bad question wastes time. It wastes your time and everyone else’s.

But a good question creates value. It clarifies something. It opens up the conversation. It leads to better understanding and better outcomes, hopefully.

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Type of Question

I think we should talk about some of the different types of question. It’s useful to think [00:07:00] about why you are asking a question. Different questions serve different purposes, and once you understand that, choosing the right type of question becomes much easier.

I have grouped these questions into different types based on my own opinion, uh, but there are many different ways to do this.

Information Questions Basics

The first type I would talk about is “information questions”.

Information questions are the most basic and most common type of question. The purpose is simple: get information.

We can divide these into closed and open questions.

Closed questions usually have one or two possible answers. Normally “yes” or “no”. They’re useful when you need something clear and specific.

For example:

Did you finish the report?”

Or

Is the meeting at 11?”

The [00:08:00] answers to these questions are either “yes” or “no“.

Yes, I finished a report.”

Open questions, on the other hand, invite explanation. They usually begin with “what”, “why“, or “how“.

Open questions are far better for learning because they give the other person an opportunity to think or explain something or share information you didn’t even know to ask for.

For example:

Why did you choose to study this subject?”

“How does this usually work?”

If your goal is understanding, rather than confirmation, open questions are almost always the better choice.

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Direction Shaping Conversation

The next set of question types are best categorized, in my opinion, as direction shaping questions. They influence the direction of a conversation.

Probing questions help you go [00:09:00] deeper. They’re often used when something isn’t clear or when you want more detail. These are especially important for English learners, because they allow you to check meaning without pretending you understand everything.

Examples include:

Could you explain that part in more detail?”

“When you say it was challenging, what was the hardest part?”

Follow-up questions are a natural extension of this. You ask them after hearing an answer, and they show that you are listening and interested.

Research consistently shows that follow-up questions make conversations more engaging and more cooperative.

There are also refocusing questions, which are really useful when a discussion goes off track. Instead of interrupting or disagreeing directly, a well-timed question can gently bring the conversation back to the main [00:10:00] point.

“What does this mean for the deadline?”

Or

So, what’s the next step from here?”

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Influencing and Feelings

Some questions are explicitly designed to influence rather than understand.

Leading questions are the most common example.

These questions suggest an answer. They suggest a preferred answer. Or they maybe include the speaker’s opinion inside the question.

They often appear in sales or persuasion, media interviews, or police interrogations.

Don’t you think this plan is too risky?”

Wouldn’t you agree that this is the best option?”

Both of those questions have an opinion in them already. “Too risky”. Best option”. So, the person you are asking the question either has to agree with you or disagree with you. And humans are much more likely to agree [00:11:00] than disagree.

The problem with this type of question is that they are risky. People may agree to just avoid conflict, or they may feel manipulated and become defensive.

In everyday conversation, leading questions can limit an honest discussion and they can damage trust. That doesn’t mean they never have a purpose, but in most conversations they should be used very carefully.

There are also questions designed to understand how someone feels or how they see a situation.

These are often called “affective questions”. They are extremely important in workplaces or in friendships. Understanding emotions helps you prevent misunderstandings and builds trust.

For example:

How do you feel about moving to a new team?”

Was that change stressful for you?”

However, these questions require cultural [00:12:00] sensitivity. In some cultures, talking openly about feelings is normal. In others, it might feel too personal or too inappropriate. Good communicators adjust their questions based on context and relationship.

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Funnel and Iterative Methods

Two useful techniques that combine several question types are funnel questions and iterative questions.

Funnel questions start broad and gradually become more specific.

They are useful in interviews or in problem solving or in discussions where you are trying to understand a complex situation step by step.

For example,

How has the project been going overall? Which part has been most challenging? What exactly caused that issue?”

You are narrowing down on the real topic.

Iterative questions build on previous [00:13:00] answers. They involve taking an answer and immediately refining it with a follow-up.

You have all probably become quite used to using iterative questions without realizing it. This is because we use iterative questions a lot when it comes to working with AI tools.

For example:

“ChatGPT, can you make a summary of this document? That’s a good summary, but can you explain it as if I were a beginner? Can you make it a little bit simpler? Can you add this? Can you take away this?”

This is an iterative question. You get an answer, a response, and you ask another question to improve the answer.

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What Makes Questions “Good”

At this point, it’s important to be clear about something. A question can be grammatically correct, but still be a bad question.

English learners [00:14:00] often focus on technical accuracy. Focus on the right word order, the correct tense, the correct question form, and of course all of that matters. But correctness alone doesn’t make a question “good”.

A good question is communicatively effective not just technically correct. A good question is clear and concise. The listener should immediately understand what you are asking without needing clarification. If a question is too long or too complicated, people stop listening. They don’t care.

Second, a good question has a clear purpose. Before you ask it, you should know why you are asking. Do you want information? Clarification? A deeper understanding? To start a conversation? To make a friend?

Third, a good question invites a useful or interesting [00:15:00] answer.

Fourth, a good question moves the conversation forward. It adds something. It helps the discussion develop instead of stopping it.

And finally, a good question respects the listener’s perspective. It doesn’t assume too much. It doesn’t push an opinion. It gives the other person room to answer honestly and in their own way.

A technically correct question shows that you know the rules of English. A communicatively effective question shows that you understand how English is actually used between people.

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Practical Tips to Improve

So how do you actually get better at asking questions? Well, here is some advice.

The first step is simple… ask more questions.

Many English learners stay quiet because they’re afraid of making mistakes. But silence often creates a [00:16:00] worse impression than imperfect English.

That said, more questions doesn’t mean endless questions. Quality matters more than quantity. Good question askers are active and they ask questions because they’re curious.

Follow up questions are one of the most powerful tools you have. They show that you are listening. They show that you care. They make conversations feel natural.

You don’t need complicated language to ask a good follow-up. Simple things work extremely well.

Why? How? What happened? What happened next?

If you want better conversations and more understanding, open questions should be your default. Open questions invite explanation, reflection, and I guess they help the other person express themselves in their own way.

A very simple example is instead of saying, [00:17:00] “do you like cats?”, say, “what is your favorite animal?” Right?

It’s a very elementary school example, but hopefully you can all understand it. Instead of saying,

Do you like something?”

“Do you want something?”

Say,

What would you like?”

“What do you want?”

“How do you do this?”

There are some clear exceptions, like business decisions or fact checking. That’s very important. When you need a confirmation or you need a final answer, closed questions are much more effective.

You just want a closed “yes” or “no” answer.

One of the easiest ways to improve your questions is to take your opinion out of them.

Leading questions limit honest answers. They push people to agree with you or they push people to stay silent, instead of expressing what they really think.

By using more neutral language, you will probably get better responses [00:18:00] and better responses lead to better conversations. If you want useful answers, let the other person do the thinking.

And short questions are usually better questions. As a general rule, try to ask a question in one clear sentence. If you need more explanation, you can always follow up later.

This is especially important in spoken English. Spoken language needs to be processed in real time and long questions increase the chance of confusion. For non-native speakers, shorter questions are also safer. They reduce mistakes and they make you sound more confident.

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Listening and Redirecting

One important piece of advice you will hear a lot is that great questions start with listening.

Listening is an active skill. When people struggle to ask good questions, the real problem is often poor listening. When you don’t listen carefully, a few things [00:19:00] happen.

You ask questions that have already been answered. You miss important details. You create awkward moments where the other person thinks that you were not paying attention.

None of this helps a conversation move forward.

Good listening means letting answers finish even if you think you already know what the person is going to say. It also means resisting the temptation to plan your next question while the other person is still talking.

Simple nonverbal signals matter. Eye contact, nodding, and small reactions show that you are engaged. These signals make the other person more comfortable and more willing to continue speaking, at least in a native English speaker context.

I know some cultures don’t necessarily like eye contact or nodding, or have different ways of showing you are engaged.

In natural conversations, topics don’t always [00:20:00] stay where you expect them to. Some of the most interesting and useful discussions happen when a conversation moves in an unexpected direction. If you are listening properly, you can recognize when it makes sense to follow the new path.

At the same time, there are moments when a conversation needs to be guided or redirected. Instead of interrupting or disagreeing, you can use questions to bring the focus back. Questions that connect the current topic to the original goal and keep the conversation moving.

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Asking Better with AI

To end this episode, I think we should talk a little bit about AI. Some people worry that AI will reduce the need for communication skills. In reality, it’s kind of done the opposite.

AI has made the ability to ask clear and good questions more important. When you use AI tools, the quality of what you get [00:21:00] depends almost entirely on the quality of what you ask.

Vague prompts lead to vague results. When you ask someone a good question, you are clear about your intent. You give enough context for them to understand the situation, and you apply constraints so that the answer is actually useful.

The same principles apply when prompting AI. This means that learning how to ask better questions transfers directly into how effectively you can use AI tools.

If you are not careful, AI can weaken your curiosity. It becomes easy to stop questioning and to accept the first response and move on. So your goal should be to use AI as a tool that works with your questions, and that only works if your questions are thoughtful and intentional.โ€‹

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Final Thought

In this episode, I’ve looked at why question asking matters more than ever, what makes a question genuinely good, and how listening, follow up questions, and AI all depend on the same skill… knowing how to ask clear and intentional questions.

My advice is simple. Start paying attention to the questions you ask. Shorten them. Open them up. And don’t be afraid to ask one more follow up.

But what do you think? Do you think you are a “good” question asker? How could you improve? Do you remember a time when you notice someone asking a bad question?

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Vocabulary Games and Activities!

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By Tom Wilkinson

Host and founder of Thinking in English, Tom is committed to providing quality and interesting content to all English learners. Previously a research student at a top Japanese university and with a background in English teaching, political research, and Asian languages, Tom is now working fulltime on bettering Thinking in English!

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