There’s an art to asking questions.
- It starts with asking better questions—the ones that invite genuine reflection.
- Then comes the quiet between asking and answering, where we let the moment breathe.
- And finally, it’s about building on their responses, letting each question lead to a deeper understanding.
The best part of my job is sitting with teenagers and hearing their unique perspectives on themselves and the world around them! Anyone with a teenager knows how challenging it can be to get them to open up. That’s why we center one of our core beliefs on asking “beautiful questions” and giving students the space to share their answers in their own way.
Here are a few questions to help teens open up and share what matters to them—beyond the usual “how was your day?”
Getting to Know Them Better:
- What’s a movie or show you’d recommend to anyone? Why?
- If you could repeat any day from the past year, which one would it be and why?
- What song or artist do you have on repeat right now?
- If you could visit anywhere in the world, where would you go?
- What’s the best book you’ve read recently?
Encouraging Self-Reflection:
- What’s something you did today that made you feel good about yourself?
- What’s a goal you’re working toward, big or small?
- What’s something you once believed but have changed your mind about?
- What’s something you’re really good at that others might not know?
Building Empathy and Connection:
- Who in your life always has your back?
- ️What’s the best advice you’ve ever given?
- What’s a small act of kindness you’ve noticed recently?
- If you could give one piece of advice to someone younger than you, what would it be?
Encouraging Curiosity and Big-Picture Thinking:
- If you could solve one big problem in the world, what would it be?
- What’s something you’d like to understand better?
- If you could learn any skill instantly, what would it be?
- What’s a question you wish more people asked?
These simple questions can spark some of the most meaningful conversations. For those interested in more ways to connect, resources like Talking Point Conversation Cards and The Book of Beautiful Questions by Warren Berger offer plenty of inspiration.
Laura Barr is a deeply experienced and passionate college consultant, founder of Emerging Educational Consulting, and creator of the Capstone Certification program. She’s dedicated to helping families and professionals navigate the college application process with simplicity, deliberation, and joy. Want to learn more about our services? Tell us your story!
