How to ask better questions: a practical guide to getting good answers

How asking the right questions can change your life. From the most everyday things to the most existential questions. Learn it!

The other day I read a statement from a journalist who talked about the privilege he had, of being able to ask any question to anyone, without embarrassment. After all, knowing how to ask questions is part of the job.

How to ask questions?

Before we develop the topic, I decided to list the main points on how to ask well-designed questions right away. You will learn to use the same techniques, secrets and tricks as journalists, doctors and detectives!

  1. Always keep clear in your head what you want to know. Take care with your aim to hit the center of the target. For example, instead of calling the mall and asking if store X is open, ask what the opening hours are. It will generate a response with more information.
  2. Use open-ended questions: Open-ended questions encourage the sharing of opinions and experiences. For example, instead of asking “Did you like the movie?”, ask “What did you find interesting about the movie we watched yesterday?”
  3. Be specific and clear: Avoid vague or ambiguous questions. For example, instead of asking “How was your day?”, ask “What interesting did you do at work today?” This will provide more concrete information and stimulate conversation. I wrote an entire post about how to make the most of that chat in the car when we pick up our kids from school: “Don’t ask me anymore how school was today.” (Try it, it works a lot!)
  4. Use relevant keywords: Include terms and keywords relevant to the context of the question. For example, if you are asking about a dish someone cooked, ask “What ingredients did you use to make this delicious lasagna?”
  5. Encourage dialogue: Ask questions that encourage the person to participate in the conversation and not just respond. For example, “What are your suggestions for improving our exercise routine?” This approach encourages participation and collaboration.
  6. Pay attention and be empathetic: Demonstrating genuine interest and understanding of the other person's point of view is essential. For example, “How did you feel when did you miss the bus this morning?” This question shows empathy and interest in the interviewee.
how to ask better questions

“Wisdom begins with doubt. Only those who doubt are in a position to ask questions. And by asking questions, you can seek the truth.”

Socrates

I would even say that questions are the best part of our most successful invention: human language, the most sophisticated on the planet. Mastering the art of asking questions can go far beyond chasing the “right” answer. Some, like rhetoric for example, don't even need any response, they are just used as an incentive to reason. Others, it has the potential to literally change your life (will you marry me?).

Others achieve a degree of intimacy that is sometimes greater than the intimacy of two bodies. These are brain meetings. Sometimes, of souls.

Questions are so valuable that there are even million-dollar ones:

“What would you do if you only had this day left?”

Anyway, questions are no small matter! They are part of our lives and are one of our greatest “powers”. So why not pay more attention to how to do them?

GOOD QUESTION! :)

I have prepared some practical tips to improve and boost your questions in everyday situations. I tried to use simple and familiar examples. Let's go?

The 10 most famous questions of all time

The 10 most famous questions of all time may vary depending on culture and context, but here are some of the most well-known and frequently cited questions throughout history:

  1. “To be or not to be, that is the question” – William Shakespeare (Hamlet)
  2. "Who am I?" – The fundamental question of philosophy and the search for personal identity.
  3. "Where we came from? Where are we going?" – Questions about the origin and destiny of humanity.
  4. "What is the meaning of life?" – A classic existential question.
  5. “Can we know the truth?” – Fundamental question of philosophy and epistemology.
  6. "What is love?" – Recurrent question in poetry, music and philosophical discussions.
  7. “What is happiness?” – A common question in the search for well-being and personal fulfillment.
  8. “How far can science take us?” – Question about the limits and possibilities of science and technology.
  9. “What is art?” – Question about the nature of artistic expression and its importance for humanity.
  10. “How can we achieve world peace?” – Question about the search for harmony between nations and individuals.

“Whoever asks a question is a fool for five minutes; whoever does not ask a question remains a fool forever.”

Chinese proverb

How to ask questions: what makes you a good questioner?

There are three qualities that define a good “asker”:

1. Curiosity

How to ask questions

Curiosity is VERY important because it drives learning, innovation and personal development. It is what allows us to expand our understanding of the world and continually improve our skills and knowledge. In a conversation, contrary to what most people imagine, the “interested” person is more captivating than the “interesting” person. Genuine questions are more exciting than that personal pitch. And, of course, much more useful.

2. Purpose

A good questioner knows that everything is in the preparation. Don't just ask on impulse. Be intentional. Choose your words with purpose and make sure you're asking at the appropriate time. Before you start asking your question, think carefully about why you are asking it. Note what you hope to learn from the answer.

3. Courage

A critical characteristic of a good questioner is courage. Many confuse this with being a fool or, even worse, bleargh. And most of the time it really doesn't go beyond that. Social media is full of these “courageous” people. But every now and then you have to put your finger on the wound and these types of questions are not easy. But it may be precisely this that will take us to the central point of a reasoning or even to a delicate point in a relationship. They usually hurt, but they can be the way to untie the knots. 

How can you start asking better questions?

Effective communication is vital for all relationships. Learning what questions to ask can improve how you work with team members, your leadership skills, and how you communicate with your employees, friends, and family. 

Here are nine tips on how you can start asking better questions:

1. Be a good listener

When someone gives you an answer or explains something to you, pay attention. In truth.

If you don't listen correctly (so-called “active listening”), you may end up asking questions that have already been answered or are not very relevant. By focusing on listening, you will avoid asking very generalized questions that you could probably already know the answer to. 

When someone is talking, maintain eye contact and use body language like nodding your head and leaning in to show that you're engaged (don't worry too much about this, if you're really interested, it just happens naturally). Knowing how to ask questions involves being a good listener first.

2. Don't be afraid to ask MORE questions

“He who asks is a fool for five minutes, but he who does NOT ask remains a fool forever.”

- Chinese proverb

If you're still confused/curious about something, keep asking. Maybe it's your first time trying a new recipe in the kitchen or you want to learn on MidJourney and chatGPT :) correctly. There's no such thing as wrong questions — especially if you've never asked them before. Think of it this way: if you don't ask your question, it will be even more annoying later in the process.

3. Search

Do you fully understand what you are asking and why? It may seem a bit schizophrenic, but look know what you are asking.

Think about your intentions so you can craft questions that will give you meaningful answers. Consider the following: 

  • Are you looking for data or an opinion? 
  • How formal or informal should you be when asking your question? 
  • Are you looking for confirmation or insight, answers or explanation?
  • Do you know what you will discover or will the information be surprising?
  • Are you looking for common ground or empathy from the other person?

People can't respond appropriately if you don't ask appropriately. It’s that famous expression “stupid question, stupid answer”. Learning how to ask questions is, first and foremost, a sign of respect.

4. Let the questions and answers lead you

Everyone goes off topic sometimes, but that's not always a bad thing. The conversation can flow in many different directions before or after your question is answered. Psychoanalysts are experts at this and work with this strategy. Instead of panicking and thinking you just need to discuss the issue, see where the conversation goes. 

Try to relax and don't think that every instance that every question must be formal.

 5. Use silence to your advantage

Questions don't need to be machine-gunned and they don't need to be a quick conversation. Pausing to listen between responses gives you time to think about what was said and ask better follow-up questions. 

Also don't feel pressured to respond quickly. Quick responses can disrupt the flow of the conversation. You don't want to feel rushed or rush others, so learn to feel comfortable with silence and give yourself time to think. 

6. Ask probing questions

Probing questions are great for promoting critical thinking, learning something new, or understanding how a person thinks.

A question that engages and prompts the other person to explore their thoughts demonstrates that you are curious about what they have to say. And asking questions that encourage exploration of emotions and ideas will lead to more fruitful conversations. 

Here are some examples:

  • What do you think is the best solution for developing a new app?
  • How did you decide this was the correct course of action?
  • What are you afraid will happen if we do this?
  • What will we do if our worst-case scenario comes true?

7. Keep your questions short

A long-winded question shows a lack of self-awareness. It might end up confusing someone more than it should. You want to provide enough detail in your query that summarizes what you are looking for in response, but not too much. 

The person you are asking should only hear your question once, not three or four times. Focusing on asking open-ended questions in one sentence can still start a good conversation. 

8. Get your streak right

Have empathy for the other party. Not everyone can open up right away and answer personal questions easily. That's why you should know how much you trust the person and keep their feelings in mind.

If you're having a long conversation with a lot to cover, give some thought to the order of your questions. You may not want to start with sensitive or challenging questions. Start by asking basic, easy questions before getting into the emotional ones. 

9. Use the appropriate tone

All questions have different purposes and meanings behind them. Some are serious, while others are light-hearted and fun. It's important to know when you should have a professional or serious tone and when you can be casual.

Being flexible and adjusting your style is key. Being overly formal in all situations can make people uncomfortable and inhibit their willingness to share information. When you ask your next question, notice the vibrations in the room or with the person you are speaking to. 

What to Avoid When Asking Questions

Setting the right tone is key to making the respondent feel comfortable enough to respond honestly and completely. Learning to tap into your emotional intelligence and reading the room are great ways to improve the quality of conversation in your professional or private life. 

When we learn communication skills that make another person feel safe, we develop deeper relationships with friends, partners, and colleagues and lead stronger teams of people. 

Here are three things to avoid when asking questions:

1. Avoid leading questions

Here there is the issue of the famous confirmation bias, a resource often used in an unprofessional way by some journalists more concerned with indoctrination than with investigation and clarification. A main question already presupposes an answer. 

The essence and main purpose of questions is to discover and learn something new from the answer. Keep your question clear, simple and if possible, without bias.

2. Don't ignore the signs

To learn how to ask questions it is necessary to read well the verbal and non-verbal cues that the respondent is sending us. 

Answering questions isn't always easy, and it can show. Pay attention to the person's body language. Is their body pointed towards you or are they facing away? Do they maintain eye contact or avoid looking at you? Does their tone, speed, and volume suggest they feel comfortable or distressed?

If the other person is showing that they're uncomfortable, respect their space—you're probably not getting good or honest answers anyway. Making the person uncomfortable won't build trust or help you get the information you need.

You must learn when to use assertiveness as a questioning technique if someone appears to be withholding necessary information. Being respectfully insistent with an employee you suspect is lying is not the same thing as being relentless with someone who shares a vulnerable experience.

3. Don’t ask “Yes” or “No” questions

Closed-ended questions that only require a “Yes” or “No” answer are great for confirming information, not for advancing a conversation. To keep the conversation flowing, ask questions that prompt your conversation partner to explore and develop ideas. 

Keep asking, always!

Questions, as I mentioned at the beginning of this text, are part of life. And learning to develop this art is worth it, as it is something you should always continue doing. 

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