The Basics of Good Questioning Skills – Knowing Who, What, Where, When, Why and How to Ask

Some of you might have seen the 1975 Monty Python film The Holy Grail, where King Arthur and his knights embark on a search for the Grail and encounter many silly obstacles. In one scene, a troll asks a series of questions to anyone wishing to pass. Some are easy. Some are bizarre. Some don’t even get answered properly before the troll reacts.

There are questions that trigger new questions. Questions that get straight answers. Questions that ask for opinions. And questions that test your knowledge. In English conversation, all kinds of questions exist—and knowing how to ask them can boost your fluency and confidence.

Let’s break down the basics of who, what, where, when, why, and how to ask great questions in English.

WHO

We ask questions to friends, family, coworkers, classmates, strangers at a café, customer service reps on the phone, Zoom meeting colleagues—really, anyone. And people ask us questions all day too. Understanding who you’re talking to helps you decide how formal or casual to be. You’ll speak differently to your professor than to your cousin.

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WHAT

There are two main types of questions:

Closed-ended questions demand short, specific answers.
Examples from the movie: “What is your name? What is your favorite color?”
These are good for quick facts, but they don’t keep a conversation going.
Open-ended questions invite someone to explain or elaborate.
“Why do you want to find the Holy Grail?” would’ve sparked a deeper conversation (and maybe avoided being thrown into the gorge!).

Open-ended questions make people feel like you care. They lead to richer, more meaningful conversations. [🔗suggested internal link: “Casual vs. Formal Conversation – Part I”]

WHERE / WHEN

You can ask questions anywhere: in a classroom, on a date, at a networking event, or while DMing on social media. The context matters. You might ask different things on LinkedIn than you would on Instagram.

You also get better with practice. Ask questions every day—in safe places like your language class, at work, or even to a YouTuber during a livestream. Over time, asking becomes second nature.

WHY

We ask to learn, connect, understand, impress, clarify, relate, even flirt. Questions give you control over the conversation. If someone mentions their job, you can dig deeper:
“What do you love most about your work?”
“Have you always wanted to be in that field?”

Francis Bacon once said, “Who questions much shall learn much and retain much.” Lou Holtz added, “I never learn anything talking. I only learn things when I ask questions.” Kids know this—just ask any 5-year-old why the sky is blue.

HOW

This is where you shine. Great questioners are also great listeners. Let the speaker respond without interrupting. Make eye contact if in person, or use encouraging gestures if on video.

You don’t need to ask 50 questions in a row. That’s exhausting. It’s better to go deep on one or two topics that actually interest both people. Think about asking:

“How did that make you feel?”
“What do you think will happen next?”

Practical Tips to Build Your Questioning Muscle:

Set a daily goal: Ask 2–3 good questions during conversations.
Use flashcards or a notebook to write and practice questions.
Pay attention to how questions are asked in movies, podcasts, and real-life interactions.
Rehearse simple question openers:
“That’s interesting—can you tell me more about ___?”
“Why do you think that is?”
These are your safety nets when your mind goes blank mid-convo.

With practice, you’ll not only ask better questions—you’ll answer better too. You’ll start to recognize the difference between “how” and “why” questions, especially in job interviews, presentations, or meetings. This means faster responses, fewer awkward silences, and more confident English.

A Word on What Not to Ask

Some questions are off-limits. In many cultures, don’t ask someone’s age, salary, weight, relationship status, or personal health unless you’re very close and they’ve invited the conversation. If you’re unsure—don’t ask. Simple.

Buying Time When You Need It

If someone’s speaking fast or you’re still thinking, try these time-buying phrases:

“That’s interesting—can you explain that a bit more?”
“Could you go back to what you said about ___?”
These phrases help you stay in the conversation while your brain catches up.

Also, body language and tone matter. Smile, nod, and show interest. People like to talk to people who actually look like they want to listen.

Final Thoughts

Watch how skilled communicators speak. Copy what works. Ditch what doesn’t. And remember:
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Good questions build great conversations.
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Who you ask, what you ask, where and when you ask, why you ask, and how you ask—it all matters.

So ask away. And enjoy the answers.

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