100 questions followed by a clear explanation of why this is a powerful tool for small group formation.
All questions are taken directly from 100 Questions That Lead to Understanding.
The 100 Questions (Clean List)
Questions 1–36: Foundational & Relational (Based on the classic intimacy framework)
Given the choice of anyone in the world, whom would you want as a dinner guest?
Would you like to be famous? In what way?
Before making a phone call, do you ever rehearse what you’re going to say? Why?
What would a “perfect” day look like for you?
When did you last sing to yourself? To someone else?
If you could live to 90 and retain either the mind or body of a 30-year-old, which would you choose?
Do you have a secret hunch about how you’ll die?
Name three things you and your partner have in common.
What are you most grateful for in life?
If you could change anything about your upbringing, what would it be?
Tell your life story in four minutes.
If you could wake up tomorrow with any one new ability or quality, what would it be?
What would you ask a crystal ball to reveal about your future?
What’s something you’ve dreamed of doing for a long time? Why haven’t you done it?
What is the greatest accomplishment of your life?
What do you value most in friendship?
What’s your most treasured memory?
What’s your most terrible memory?
If you knew you’d die in one year, what would you change?
What does friendship mean to you?
What role do love and affection play in your life?
Share five positive things about someone close to you.
How close was your family growing up?
How do you feel about your relationship with your mother?
Make three true “we” statements.
Complete this sentence: “I wish I had someone with whom I could share…”
If we were to become close friends, what would I need to know about you?
Tell your partner what you like about them already.
Share an embarrassing moment.
When did you last cry in front of another person? Alone?
Tell your partner something you like about them that you don’t usually say.
What, if anything, is too serious to be joked about?
If you died tonight, what would you most regret not telling someone?
If your house caught fire, what would you save after people and pets?
Whose death in your family would you find most disturbing? Why?
Share a personal problem and ask for advice.
Questions 37–52: Identity & Values
What dream feels almost too big to say out loud?
What scares you most about the future?
What gives you the most hope about the future?
What part of yourself are you still learning to accept?
What do you want your legacy to be?
What do you want to be remembered for by those closest to you?
If you could relive one day exactly, which would it be?
If you could undo one decision, which would it be?
What is the hardest truth you’ve faced about yourself?
What is the kindest thing anyone has done for you?
What is the most courageous thing you’ve ever done?
What is the most beautiful memory you carry?
What is one thing you’ve never said out loud but wish someone knew?
What is one thing you are most proud of about yourself?
What mistake are you grateful for?
What belief did you once hold strongly but no longer do?
Questions 53–68: Dreams & Inner Growth
What truth do you still struggle to believe about yourself?
What is the most surprising thing you’ve learned about yourself?
What risk changed your life?
What promise have you made to yourself?
What question do you wish people asked you more often?
What question do you wish people stopped asking you?
What have you forgiven yourself for?
What are you still working on forgiving yourself for?
What fear have you overcome?
What fear still lingers?
What habit are you proud of building?
What habit do you wish you could break?
What belief do you hold that others disagree with?
What belief have you changed your mind about recently?
What memory always makes you smile?
What memory always makes you cry?
Questions 69–100: Resilience, Meaning & Wisdom
What is the most life-changing advice you’ve received?
What is the best decision you’ve ever made?
What is the hardest decision you’ve ever had to make?
What choice do you not regret, even though it cost you?
What is something you’ve created that you’re proud of?
What is something you’ve destroyed, and how do you feel about it now?
What is something you’ve had to let go of unwillingly?
What have you held onto longer than you should have?
What do you wish you had discovered sooner?
What do you wish you could unlearn?
What have you learned from someone much younger than you?
What have you learned from someone much older than you?
When do you feel most at peace?
When do you feel most alive?
What does “home” mean to you now?
What relationship taught you the most about yourself?
What hardship shaped you the most?
How do you define strength today?
What does healing mean to you?
What keeps you going on hard days?
How has failure changed you?
What does forgiveness look like for you?
What truth do you wish people understood about you?
What does success mean to you now?
What do you trust yourself about more than before?
What makes your life meaningful?
What responsibility do you feel toward others?
What do you feel called to do next in life?
What do you need more of right now?
What do you need less of right now?
What would you tell your younger self?
What would you like to ask your future self?
Why This Is a Powerful Tool for Small Group Formation
This is not just a question list. It is a group-building engine.
1. It Accelerates Trust Formation
Small groups typically take months to move from surface conversation to real connection. These questions compress that timeline into weeks—or even a single session.
2. It Equalizes Power
There are no experts here. Everyone answers as a human being, not as a title, role, or status. That is ideal for:
Church small groups
New member integration
Leadership cohorts
Multigenerational groups
3. It Creates Natural Group Sorting
As people answer, affinity clusters emerge organically:
Shared values
Shared struggles
Shared hopes
This makes it an excellent discernment tool for forming long-term small groups based on depth, not demographics.
4. It Scales Across Contexts
The same questions work for:
Faith-based groups
Community groups
Recovery circles
Youth and young adult ministries
Leadership and discipleship tracks
5. It Moves Groups From Attendance → Belonging
People don’t stay because of programming.
They stay because someone knows their story.
These questions systematically create that knowing.
Bottom Line
This list can function as:
A small-group curriculum
A new-member integration pathway
A leadership formation tool
A relational discipleship framework
Used well, it doesn’t just form groups.
It forms communities.
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