25 Questions To Ask People To Draw Them Out

As a personal coach, I use pointed and thoughtful questions to help my clients gain more clarity about themselves and to help me better understand my clients and their goals.
I generally ask open-ended questions that can’t be answered with a simple “yes” or “no” so that the client is encouraged to dig deeper and uncover answers they may not have realized previously. Often after I ask a question, a client will say, “I’ve never thought about that before.” Once they ponder the question and their feelings about it, it can lead to a profound insight or an “ah ha” moment.
Even in social or casual settings, asking the right questions can stimulate deeper and more interesting discourse. It can set the stage for discovering common interests, developing a more authentic connection, and fostering mutual empathy and understanding.
There is an art to asking good questions. No one wants to feel as though they’re in a job interview or being grilled for information. A big part of asking questions is listening mindfully to the reply in order to hear beyond the words spoken.
Mindful listening requires watching body language, hearing tone of voice, and being sensitive to what is left unspoken. It also requires asking thoughtful follow-up questions or making reflective or supportive statements. By learning to ask good questions and taking the time and interest to listen mindfully, you are setting the stage for more intimate, fulfilling, and enjoyable relationships.

 Here are 25 questions to ask people to draw them out . . .

1. What is your best childhood memory?

This question always makes people smile and often leads to a humorous or poignant exchange about family, travel, holidays and traditions, hopes and dreams, and friendship. You learn a lot about someone when they share aspects of their childhood.

2. If you had a chance for a “do-over” in life, what would you do differently?

This question gives insight into a person’s state of mind about who they are, their vulnerabilities, and their hopes and dreams. Often sharing regrets or unmet desires opens doors to considering new possibilities or the confidence to make needed change.

3. How did the two of you meet?

This is a great question to ask a couple. Quite often sharing the story of how they met draws them together in a mutual happy memory. It gives them a reason to reconnect and allows you to learn more about their past and how they interact together as a couple.

4. What do you feel most proud of?

This question makes people feel you are really interested in them and who they are. Everyone wants to feel accomplished and proud, and we all want an opportunity to share our successes without looking like a braggart. The answers give you great insight into what the person values most in life.

5. What is your favorite music?

The music we enjoy helps define us and reflects the dreams and attitudes of our generation. What we listen to reflects what speaks to our souls. It reveals who we are and what we believe — in an illuminating and honest way that’s often hard to put into words.

6. If you could travel anywhere, where would you go and why?

This question not only allows you to discuss and share travel experiences, but also it affords insights into the other person’s interests, personality, and sense of adventure.

7. If you could only keep five possessions, what would they be?

This question really makes people think. We are so attached to our possessions, but truthfully there are only a few that matter deeply to us. When people are forced to define those few, it gives insight into what they value most.

8. What teacher in school made the most impact on you and why?

Teachers can play a pivotal role in helping us develop a love of learning, discover our life passions, and draw out our innate skills. Sometimes they are people who inspire us or who simply believe in us and want the best for us.

9. What do you want your tombstone to say?

Although this is a morbid question, it does go right to the heart of what we want for ourselves. At the end of our lives, how do we want to be remembered and what legacy do we want to leave?

10. What was one of your most defining moments in life?

This is a great question to invite sharing on a deeper and more vulnerable level. Often defining moments come during profound life transitions like death, divorce, job loss, etc. It is during these times we are called to make a huge mental, physical, or emotional shift.

11. Why did you choose that profession?

The story of how someone landed in a particular profession opens the door to learning a lot about a person and their motivations, interests, education, and ambitions. We spend most of our days working, so the answer to this question also reveals how a person chooses to define their lives.

12. How do you spend your free time?

This is a great follow-up question to the previous question. It rounds out the picture of how this person has created his or her life and what hobbies, interests, and obligations they have created for themselves.

13. If you won the lottery, what would you do?

This is a fun question that reveals so much about a person and their attitudes about money, work, and life passion. Would they leave their job? Buy their dream home? Do something altruistic? Would they be happy about having a lot of money or want to avoid it?

14. Who do you most admire in life?

This is a great question to learn more about the kind of person someone wants to emulate. We admire people whose actions and character reflect what we want in ourselves. This will tell you a lot about the true character of a person.

15. What are your top three favorite books and why?

Sharing favorite books opens the door for interesting conversation and finding common ground between you. It gives you and the other person a chance to learn something new and potentially to understand a new perspective or interest you haven’t pursued.

16. What are you most afraid of?

This is a very probing and enlightening question. Everyone has fears, and our fears reveal our vulnerabilities and pain. When someone shares this with you, you must respond with care, kindness, and trustworthiness. You must treat their fears with dignity so they feel safe connecting with you on this more intimate level.

17. What feels like love to you?

Everyone has their own “love language” — the words, behaviors, and attitudes that make them feel loved and that reveal how they express love. This is a great question to ask your spouse, romantic partner, or a potential romantic partner.

18. What is your strongest personal quality?

Most people feel uncomfortable with this question at first because they want to appear modest. But truly we all want to feel validated about our positive  qualities and have others recognize this about us. People will usually follow up by asking this question of you, and it creates a positive feeling and bond between you.

19. What was your most embarrassing moment?

This is a fun question that can lead to laughter and connection. Most people enjoy telling funny stories about themselves if there isn’t shame or guilt involved. Occasionally someone will reveal something painful or shameful, and this is the time to show empathy and caring.

20. If you were president, what is the first thing you would do?

You can learn a lot about someone’s political beliefs, ideals, worries, and values when you ask this question. If you want to connect and invite open discussion, just be sure you don’t challenge or put down the response you get if it happens to be different from what you would do.

21. What age do you feel right now and why?

Ask this question of someone over 50, and you’ll get some interesting responses. As we get older, most people don’t “feel” their chronological age. It’s enlightening to learn how people perceive themselves internally even though externally they may be at a completely different stage of life.

22. If you could witness any event of the past, present, or future, what would it be?

This is a fascinating question that invites interesting discussion. You can learn about someone’s interests and goals, and perhaps you’ll be inspired to delve into a new interest yourself.

23. What is a skill you’d like to learn and why?

Most of us have something we want to learn to improve ourselves or for simple enjoyment. This question gives the person the opportunity not only to share that desire, but also to examine why they haven’t pursued learning the skill.

24. What does a perfect day look like to you?

Thinking about this question requires us to dig around in our memories for previous perfect days. It’s a feel good question that gives both people an infusion of happiness and maybe even the desire to recreate that perfect day.

25. How would your friends describe you?

This question allows the other person to talk about themselves from an outside perspective. It invites self-awareness and self-honesty and opens the door to more authentic conversation.