Ask Better Questions

Houston Kraft · December 12, 2017

In a time when we are connected digitally, we are also more isolated than ever. We must continue to teach, explicitly, the skills of building meaningful relationships. One of the most foundational skills of interpersonal relationships is asking great questions.


In working with over 500 schools across the country, I have noticed that when I ask students to engage in conversation with a partner they don’t know that well, there seems to be an immediate spike in sweat and discomfort in the room. It’s not that kids don’t want to be connected to one another - it’s that they don’t know how to do it.

Consider this: most of the way we communicate today via phone is short, shallow, and sent at our leisure. Text messages, tweets, snapchats. Perhaps even more importantly, education for many today has become transactional - meaning most students identify getting good grades as more important than the experience of learning.

The byproduct? When I ask students to talk about any given prompt, Partner 1 shares and then Partner 2 shares and then they stand awkwardly looking at the ceiling or their phone or their neighbor. Why? Because the “assignment” I gave them was over.

So, I dive right in and talk about how conversation and connection isn’t transactional! That, no matter what question I asked and when you each finished answering it, there is ALWAYS more to learn about a person and we must practice and cultivate curiosity in the stories of others.

I’ve started to compile some meaningful questions to help young people practice the art of great question asking. What if, at the beginning of each class, you spent the first 2-3 minutes having students engage each other in great conversation to prime the pump for the learning to come? You build relationships in your class AND you get their brains primed for what comes next.

Here’s the list. Obviously, some of these questions are meant for smaller groups, groups that have established trust, or a different setting than your classroom:

Economic Class Background;

  1. Growing up, did you feel like you had equal access to the things you wanted as the people around you?

  2. The people you live with - what do they do for work?

  3. Do you believe that money is more often helpful or more often hurtful? What is your personal relationship to money?

  4. Have you ever saved up for something you really wanted? What was it? How long did it take until you got it?

  5. If you had unlimited money, what would you want to buy first?

Psychological Maturity;

  1. What is the thing that is irresistible to you? What thing tests your willpower?

  2. What do you think your role at school is? What do you think your role at home is?

  3. How do you decide who your friends are? What are the qualities, to you, of a great friend?

  4. How do you process strong emotions? Do you talk to a close friend or family member? Do you tend to bottle them up? Do you channel them in other ways?

Ethical/Racial Identity;

  1. What is one thing you love about your culture or ethnicity? What is one thing that makes you feel trapped by your culture or ethnicity?

  2. Tell me about a time where you felt judged or discriminated against because of the color of your skin or the cultural background you come from?

  3. How do you honor your heritage? Is there anything you do that is counter-cultural for your background?

Chronological/Developmental Challenges;

  1. Tell me about your earliest, most vivid memory of being a kid.

  2. What has been the biggest hurdle or challenge you’ve overcome to become the person you are today?

  3. What period of your life have you grown the most in? How did you grow or what did you learn?

  4. Share with me the 3 things, moments, memories, or experiences that stand out most in your life so far.

Trauma and other Threats to Well Being;

  1. Tell me about a time in your life where you felt really scared.

  2. How do you define the difference between pain and suffering?

  3. What helps you heal through pain or find hope when you are suffering?

  4. Tell me about a time when you had to forgive someone (or yourself) for something that they did.

Family Background and History;

  1. Who do you consider to be family in your life?

  2. What is your favorite family tradition?

  3. Tell me about a memory that makes you laugh when you think about a member of your family.

  4. Who in your family has been the most positive influence in your life and why?

  5. What are or what do you want to be the 3 most important elements of being a part of your family?

Unique Physical Characteristics;

  1. What makes you entirely unique - different, you believe, than anyone else in the world?

  2. What part of your body makes you feel most confident? Most unconfident?

  3. How does your physical self affect your mental self and vice versa?

  4. How do you define beauty? How does the world define beauty? What is an important difference you want people to understand between those two?

  5. What is one weird thing you can do with your body?

Location of Residence and Languages Differences;

  1. Where do you feel most at home?

  2. How often have you moved in your life? Which time was the hardest and why?

  3. What physical location makes you feel the most comfortable? Most uncomfortable?

  4. What things are a part of the Universal Language to you?

  5. How does the way you speak affect the way you are perceived?

Other meaningful questions to grow in understanding:

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

  2. If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?

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

  4. What would you do differently if you knew that no one was judging you?

  5. What are the things that stand between you and complete happiness?

  6. How would you describe yourself in 5 words?

  7. What, if anything, is too serious to be joked about?

  8. If you could ask a single person one question, and they had to answer truthfully, who and what would you ask?

  9. What do you “owe” yourself?

  10. Whose life have you had the greatest impact on?

  11. What do you like most about yourself? If you could change one thing, what would it be?

  12. Who do you most admire or look up to and why?

  13. What frustrates you about the world? What is the greatest challenge we face?

  14. What do you feel is your mission or purpose in life?

  15. Where do you feel the most safe? Why?

  16. What is the most common thing you feel judged for? How do you feel you are perceived and what feels right or not right about that?

  17. What is your greatest fear? How does it shape you? Why are you afraid of it?

  18. What brings you the greatest happiness? How often do you pursue it? What gets in the way of it?

  19. If you could change one thing about your life so far, what would it be?

  20. What challenge holds you back currently and how do you want to conquer it?

  21. What is your definition of love? How have you come to that conclusion? When do you feel the most loved?

  22. If you could travel for one month with one person - where would you go and with who? Why?

  23. What is the most important advice anyone has ever given you? What is the most important advice you have to give?

  24. What are the words or ideas that you live by? How often do you challenge or reflect on them?

  25. Talk about a time when you’ve treated someone really poorly. Talk about a time when you’ve treated someone really kindly.

  26. What has been the hardest thing you’ve dealt with with your friends? With your family?

  27. How do you want to change your school? Your community? Your world?

  28. If you could snuggle with any cartoon character, who would it be and why?

  29. If you could be related to any celebrity or historical figure, who would you want to be related to and how? Why?

  30. What is your favorite sound? Your favorite taste? Your favorite sight?



Houston Kraft

Houston Kraft is the co-founder of CharacterStrong. He is a professional speaker and kindness advocate who has spoken at over 600 events internationally. Student Body President in High School, Class President at Bowdoin College, Leadership Camp Staff for 14 years in Washington - he is a lifelong learner of character, culture, kindness, and leadership. He was featured in 2019 on BBQ Lays Potato Chips and his mom's lasting life lesson is "Hug like you mean it."