Story Questions to Ask
Engaging questions to uncover stories, create meaningful connections, and spark deeper conversations with anyone.
1What's the most interesting thing that happened to you this week?
Click to see why this works
What's the most interesting thing that happened to you this week?
Click to see why this works
Why this works
Opens up recent experiences and encourages storytelling about current events and daily life.
2What's a childhood memory that still makes you smile?
Click to see why this works
What's a childhood memory that still makes you smile?
Click to see why this works
Why this works
Reveals positive early experiences and shows what moments of joy and innocence they treasure.
3What's the most unexpected thing that ever happened to you?
Click to see why this works
What's the most unexpected thing that ever happened to you?
Click to see why this works
Why this works
Encourages sharing of surprising experiences and shows how they handle unexpected situations.
4What's a time when you felt truly proud of yourself?
Click to see why this works
What's a time when you felt truly proud of yourself?
Click to see why this works
Why this works
Reveals their achievements and shows what accomplishments they value most and why.
5What's the funniest thing that ever happened to you?
Click to see why this works
What's the funniest thing that ever happened to you?
Click to see why this works
Why this works
Encourages humor and shows their sense of comedy and what they find amusing or entertaining.
6What's a moment when you felt completely at peace?
Click to see why this works
What's a moment when you felt completely at peace?
Click to see why this works
Why this works
Reveals their sources of calm and shows what environments or experiences bring them tranquility.
7What's a time when you learned something important about yourself?
Click to see why this works
What's a time when you learned something important about yourself?
Click to see why this works
Why this works
Encourages self-reflection and shows what insights they've gained about their own character and abilities.
8What's the most beautiful place you've ever been?
Click to see why this works
What's the most beautiful place you've ever been?
Click to see why this works
Why this works
Reveals their appreciation for beauty and shows what natural or cultural environments they find most inspiring.
9What's a time when you felt completely understood by someone?
Click to see why this works
What's a time when you felt completely understood by someone?
Click to see why this works
Why this works
Shows their need for connection and reveals what kind of understanding and empathy they value most.
10What's a moment when you felt completely lost or confused?
Click to see why this works
What's a moment when you felt completely lost or confused?
Click to see why this works
Why this works
Encourages vulnerability and shows how they handle uncertainty and difficult emotional states.
11What's a time when you surprised yourself with what you could do?
Click to see why this works
What's a time when you surprised yourself with what you could do?
Click to see why this works
Why this works
Reveals their self-discovery and shows what challenges they've overcome that exceeded their expectations.
12What's a moment when you felt completely grateful?
Click to see why this works
What's a moment when you felt completely grateful?
Click to see why this works
Why this works
Shows their appreciation for life and reveals what experiences or people they're most thankful for.
13What's a time when you felt completely inspired?
Click to see why this works
What's a time when you felt completely inspired?
Click to see why this works
Why this works
Reveals their sources of motivation and shows what ideas or experiences spark their creativity and drive.
14What's a moment when you felt completely alone?
Click to see why this works
What's a moment when you felt completely alone?
Click to see why this works
Why this works
Encourages sharing of difficult experiences and shows how they handle isolation and loneliness.
15What's a time when you felt completely connected to someone?
Click to see why this works
What's a time when you felt completely connected to someone?
Click to see why this works
Why this works
Shows their need for intimacy and reveals what kind of connections they value most in relationships.
16What's a moment when you felt completely free?
Click to see why this works
What's a moment when you felt completely free?
Click to see why this works
Why this works
Reveals their desire for liberation and shows what experiences or situations make them feel most unconstrained.
17What's a time when you felt completely challenged?
Click to see why this works
What's a time when you felt completely challenged?
Click to see why this works
Why this works
Shows their approach to difficulty and reveals what kinds of challenges they find most engaging or difficult.
18What's a moment when you felt completely loved?
Click to see why this works
What's a moment when you felt completely loved?
Click to see why this works
Why this works
Reveals their need for affection and shows what kind of love and care they value most.
19What's a time when you felt completely hopeful?
Click to see why this works
What's a time when you felt completely hopeful?
Click to see why this works
Why this works
Shows their optimism and reveals what experiences or people give them hope for the future.
20What's a moment when you felt completely yourself?
Click to see why this works
What's a moment when you felt completely yourself?
Click to see why this works
Why this works
Reveals their authentic self and shows what environments or situations allow them to be most genuine.
Best Practices for Storytelling Conversations
Expert tips and techniques for getting the most out of these questions.
Best Practices
Listen Actively
Give your full attention to the storyteller and show genuine interest in their experiences and perspectives.
Ask Follow-Up Questions
Encourage deeper exploration of their stories by asking about details, emotions, and outcomes.
Share Your Own Stories
Create a mutual exchange by sharing your own experiences and stories to build connection and trust.
Question Sequences
The Recent Experience Sequence
The Emotional Journey Sequence
Common Pitfalls
Don't Interrupt the Story
Allow the storyteller to complete their thoughts and avoid jumping in with your own experiences too quickly.
Avoid Judging Their Stories
Listen without judgment and avoid making assumptions about their experiences or how they should have handled situations.
Don't Rush the Process
Give them time to think and share their stories without rushing or pushing for quick answers.