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Advanced Questioning Skills

When your English reaches an intermediate level, you can begin to improve your conversation skills by learning how to ask questions that require more thought to answer. Interesting questions are thought-provoking questions that make people think. Everyone – both native and non-native speakers – can benefit from this skill.

If you are looking for basic information on how to form questions, I recommend my affiliate Shayna’s post: An Easy Way To Form (Almost) Any Question In English.

We can think of these types of questions as interesting questions because they require more thought than questions that ask for factual details. They require more critical thinking (the art of analyzing thinking and evaluating thinking with the goal of improving it) than yes/no questions.

Critical thinking involves thinking like a detective. It helps us develop our opinions and views of the world. Asking thought-provoking questions helps create deeper and more enjoyable conversations. Our focus here is on initial questions, or starter questions, that can be used to introduce topics and begin conversations.

Related post: How to create interesting follow-up questions.

*For more information on critical thinking, check out this four minute TED-Ed video: 5 tips to improve your critical thinking by Samantha Agoos.

Before looking at critical thinking questions, we will look at basic questions that are not inherently (naturally, existing as a basic part) interesting and do not require any critical thinking.

Yes/No Questions Are Not Interesting Questions

Almost everyone is already good at asking and answering yes/no questions. Yes/no questions require very little thought to answer because they only require a one-word answer. Unless the speaker goes beyond just answering the question, these questions do not advance a conversation very far. They really limit conversations when someone’s answer is no.

Examples:

• Do you like sports?
• Can you play a musical instrument?
• Do you like chicken?
• Did you have a nice weekend?
• Are you happy?

Declarative Questions Are Not Interesting Questions

Another type of yes/no question is a declarative question or a statement question. This question form seems to be very common in Korea, and is basically just a yes/no question.

Examples:

• You like sports?
• You play a musical instrument?
• You like chicken?
• You had a nice weekend?
• You were happy?

As you can see, these have the same meaning as the yes/no questions, but they are not in question form; they are in statement form. I rarely hear native speakers use these. They are not common in interesting conversations. Try not to overuse them. Challenge yourself to start forming more complex questions.

Below, you will learn 3 easy ways to start asking more interesting questions.

First, let’s turn some of the questions above into better, more interesting and thought-provoking questions.

To do so, we need to use one of the 7 question words (who, what, when, where, why, which, how) to create more open questions.

Open questions require more than a short, one word answer. They require some thought to answer.

Thought-Provoking Questions

• Why do you think so many people like sports?
• What role does music play in people’s lives?
• What do you think about vegetarianism?
• How would you describe your ideal weekend?
• What are 3 things that always make you feel happy?

Factual Questions Are Not Interesting Questions

A factual question can be answered with one word or a short phrase. The answer is factual or obvious/easily known. These types of questions are still basic questions that do not require critical thinking, but they require more than just a yes/no answer.

Examples:

• When is your birthday?
• What is your favorite color?
• Who is your favorite musician?
• What did you eat for lunch?
• Where did you eat yesterday?
• How many classes are you taking?
• Which class is your favorite?

Factual questions are better for conversations than yes/no and declarative questions, but they are still closed questions that do not require much thinking. They are limited. Some of them CAN lead to interesting conversations, but at some point, for a conversation to REALLY develop and move beyond facts, likes, and dislikes, we need to learn to ask more interesting and thought-provoking questions.

Thought-Provoking Questions Are Interesting Questions!

Thought-provoking questions are questions that make us think. When someone asks a thought-provoking question, we can share our ideas, thoughts, experiences, and stories with them.

We create deeper and more meaningful connections, expand our ideas, and even explore new ways of thinking.

We can choose interesting topics that we enjoy discussing, or we can ask questions that have universal themes that are meaningful to everyone (love, beauty, success, hope). Thought-provoking questions are not closed like yes/no questions. They are open and often begin with Why, How, If, and What would you.

3 Types of Interesting Questions

1. Asking about experiences and interests
2. Asking about ideas, opinions, and concerns
3. Asking hypothetical questions

Experiences and Interests

These are the easiest forms of thought-provoking questions but can sometimes be uninteresting. We can take these questions to a more interesting level by focusing on specific experiences and by using superlative adjectives (best, most, happiest, etc.).

You can use the following sentence frames to form these kinds of questions:

• Who/What/When/Where + is/are/was/has been + superlative adjective (the/your + best/most interesting/happiest/most important/funniest) + _____________?

Examples:

• Who is the most interesting person you know?
• What is the best gift you have ever received?
• Where is your favorite place in Seoul?
• Who has been the most helpful person in your life?
• When was a time you felt ________________? (*This structure is a little different, but also asks about an experience.)

As you can see, some of these are still questions that CAN be answered with one word or phrase, but the structure of the questions are ones that are more likely to lead to a story or to help us get to know someone better.

Not everyone is comfortable answering personal questions or sharing their experiences. However, we can depersonalize questions by asking them another way. This leads us into the area of ideas and opinions.

Let’s look at some examples using the same topics as above.

Depersonalized Questions

• What makes someone interesting?
• What makes a gift special?
• What are the qualities that make a city likable?
• What are the qualities of a helpful person?
• What are some situations that make people feel ________________?

Ideas, Opinions, and Concerns

Questions about ideas and concerns include current events, news, and abstractions (ideas and concepts). If they are controversial (hot, likely to cause disagreement and upset people), they can be difficult. Not all questions are controversial. However, it is important to be open-minded and show respect for other people’s opinions when discussing some topics.

It takes skill to learn to disagree politely and not get too worked up (angry or upset) about certain topics. In cases where people cannot have a respectful discussion, it is better to avoid certain topics.

If someone suggests a topic that you would rather not discuss, it is okay to say, I’d rather not talk about this right now. or Would it be okay if we changed the topic?

It is important to be respectful and avoid topics that might be upsetting or inappropriate. Be sure that all participants are willing and able to have a respectful discussion before talking about topics that may be sensitive.

You can use the following sentence frames to ask about ideas, opinions, and concerns.

Sentence Frames:

• What does _________________ mean to you?
• How do you think ______________________________?
• What  ______________  are you concerned about?
• What do you think about ______________________?
• Why do you think ______________________________?
• How do you feel about ________________________?
• Did you hear about ____________________________? (*While this is a yes/no question, it can be a good way to introduce a current event/news item.)

Examples:

• What does success mean to you?
• How do you think we can end racism?
• What global problem are you concerned about?
• What do you think about sports players being exempt from military service?
• Why do you think some people choose not to have children?
• How do you feel about mandatory English education in Korean universities?
• Did you hear about the summit between Kim Jong-un and Moon Jae-in?

These are just some examples of how to ask about ideas, opinions, and concerns. There are more, including the ones above using What makes…. and What are the qualities of…. We can also add What are the advantages/disadvantages of ______________?

Hypothetical Questions

Hypothetical questions are those that ask about imaginary (not real) situations. These questions are not as common in everyday conversations, but they can be fun to think about and discuss. They can also help us get to know people (and ourselves!) better.

Sentence frames:

• Wh- (Who, What, Where, etc.) would you _____________ if you could _________________?
• If you had ______________, what would you ________________?
• What would you ________________ if you were _____________?
• If you had to choose between ______and _______, which would you choose?

Examples:

• Where would you go if you could travel anywhere in the world?
• If you had to spend $1,000 today, what would you buy?
• What would you change if you were president?
• If you had to choose between love and money, which would you choose?

Hypothetical questions can be helpful when we don’t have experience with something. For example, if we have never traveled to another country, we can imagine and think about different choices and ideas related to travel. While the grammar is more advanced, with practice, you can learn and remember the structure of hypothetical questions.

*For more information about hypothetical questions and the grammar related to them, check out Hypothetically, What Would You Do?

In Conclusion

The key to having more interesting conversations is asking more interesting questions. It involves sharing our thoughts and experiences with others when they ask us questions.

This style of conversation might feel strange or make you uncomfortable if you come from a collectivist culture where members of society are expected to agree with others in order to maintain harmony. If you fear the judgment of others, you might feel uncomfortable sharing your opinion.

It can take time to get used to having conversations in English due to cultural differences that affect language and communication styles. This inquiry-based style of communication is common in individualistic cultures in which people are encouraged to ask questions and develop their own opinions from a very young age. This style of communication goes back to ancient Greece and Socrates, but that is a topic for another day.

If you want to master English, being able to shift into this style is essential. It will be challenging, but with great challenges, come great rewards. Try to have fun and embrace the learning process!

Next on your reading list: How to Ask Better Follow-up Questions

Grammar Refresher

Espresso English is one of my favorite sites for easy English lessons.
You’ll find both free content, like the post below, and courses and e-books for purchase.

If you need a refresher on the grammar aspect of forming questions, I recommend a visit to the following post by my affiliate, Espresso English: An Easy Way To Form (Almost) Any Question In English.

Never stop learning!
~ Trey