Great Questions

After 20 years of listening, we know what makes a good conversation: Start by asking Great Questions.

Here are some of our suggestions for getting a good conversation going. We encourage you to use the ones you like and to come up with your own. This list is in no particular order. Choose one of the categories below, or scroll through and read them all.

Great Questions for Anyone

• Can you tell me about the important people in your life?
• What have been some of the happiest moments in your life? The saddest?
• Who has been the biggest influence on your life? What lessons did that person or those people teach you?
• Can you tell me about a moment when a person’s kindness made a difference in your life?
• What are the most important lessons you’ve learned in life?
• What is your earliest memory?
• What is your favorite memory of me?
• Are there any funny stories your family tells about you that come to mind?
• Are there any funny stories or memories or characters from your life that you want to tell me about?
• What are you proudest of?
• When in life have you felt most alone?
• If you could hold on to memories from your life forever, which would they be?
• How has your life been different than what you’d imagined?
• How would you like to be remembered?
• Do you have any regrets?
• What does your future hold?
• What are your hopes for what the future holds for me?
• What are your hopes for my children?
• If this was to be our very last conversation, is there anything you’d want to say to me?
• For generations listening to this years from now, is there any wisdom you’d want to pass on to them? What would you want them to know?
• Is there anything that you’ve never told me but want to tell me now?
• Are there things about me that you’ve always wanted to know but have never asked?
• If you could talk to a younger version of yourself, what would you say?
• What were your first impressions of me? How did they change?

Friends or Colleagues

• If you could interview anyone from your life living or dead, but not a celebrity, who would it be and why?
• What is your first memory of me?
• Was there a time when you didn’t like me?
• What makes us such good friends?
• How would you describe me? How would you describe yourself?
• Where will we be in 10 years? 20 years?
• Do you think we’ll ever lose touch with each other?

Grandparents

• Where did you grow up?
• What was your childhood like?
• Who were your favorite relatives?
• Do you remember any of the stories your grandparents used to tell you?
• How did you and grandma/grandpa meet?
• What was my mom/dad/parent like growing up?
• Do you remember any songs that you used to sing to your children? Can you sing them now?
• Were your grandparents well-behaved?
• What is the worst thing your grandparents ever did?
• What were your parents like?
• What were your grandparents like?
• How would you like to be remembered?
• Are you proud of me?

Raising Children

• When did you first find out that you’d be a parent? How did you feel?
• Did you always know you wanted to be a parent?
• Can you describe the moment when you saw your child for the first time?
• How has being a parent changed you?
• What have you learned about yourself from being a parent?
• What are your dreams for your children?
• Do you remember when your last child left home for good?
• Do you have any favorite stories about your kids?

Parents

• Do you remember what was going through your head when you first saw me?
• How did you choose my name?
• What was I like as a baby? As a young child?
• Do you remember any of the songs you used to sing to me? Can you sing them now?
• What were my siblings like?
• What were the hardest moments you had when I was growing up?
• If you could do everything again, would you raise me differently?
• What advice would you give me about raising my own kids?
• What are your dreams for me?
• How did you meet mom/dad?
• How do you think we are alike? How do you think we are different?
• Are you proud of me?

Growing Up

• When and where were you born?
• Where did you grow up?
• What was it like?
• Who were your parents?
• What were your parents like?
• How was your relationship with your parents?
• Did you get into trouble? What was the worst thing you did?
• Do you have any siblings? What were they like growing up?
• What did you look like?
• How would you describe yourself as a child? Were you happy?
• What is one of your best memories of childhood? Worst?
• Did you have a nickname? How’d you get it?
• Who were your best friends? What were they like?
• How would you describe a perfect day when you were young?
• What did you think your life would be like when you were older?
• Do you have any favorite stories from your childhood?
• When you were a child, what did you want to be when you grew up?

School

• Did you enjoy school?
• What kind of student were you?
• What would you do for fun?
• How would your classmates remember you?
• Are you still friends with anyone from that time in your life?
• What are your best memories of grade school/high school/college/graduate school? Worst memories?
• Was there a teacher or teachers who had a particularly strong influence on your life? Tell me about them.
• Do you have any favorite stories from school?

Teachers

• When and why did you decide to become a teacher?
• Tell me about your first day as a teacher.
• How is teaching different from how you imagined it to be?
• Tell me about a time when teaching made you feel hopeful.
• What are the most challenging and/or funniest moments you’ve experienced in the classroom?
• How would you like your students to remember you?
• Was there a teacher or teachers who had a particularly strong influence on your life? What did you learn about teaching from them?
• Looking back, what advice would you give to yourself in your first year of teaching?

Love & Relationships

• Do you have a love of your life?
• When did you first fall in love?
• Can you tell me about your first kiss?
• What was your first serious relationship?
• Do you believe in love at first sight?
• Do you ever think about previous lovers?
• What lessons have you learned from your relationships?
• Who were the “ones that got away” in your life?
• What was the hardest break up you’ve ever experienced?
• Do you remember the best date you ever went on?/Do you remember your first date?

Marriage & Partnerships

• How did you meet your spouse/partner?
• How did you know they were “the one”?
• How did you propose?
• What were the best times? The most difficult times?
• Did you ever think of getting divorced?
• Did you ever get divorced? Can you tell me about it?
• What advice do you have for young couples?
• Do you have any favorite stories from your marriage or about your spouse/partner?

Working

• Describe the work that you do.
• Tell me about how you got into your line of work.
• Do you like your job?
• What did you think you were going to be when you grew up?
• What did you want to be when you grew up?
• What lessons has your work life taught you?
• If you could do anything now, what would you do? Why?
• Do you plan on retiring? If so, when? How do you feel about it?
• Do you have any favorite stories from your work life?

Religion

• Can you tell me about your religious beliefs/spiritual beliefs? What is your religion?
• How did you come to your faith? From your family? From a particular experience or set of experiences?
• How has your faith evolved over time?
• Have you experienced any miracles?
• What was the most profound spiritual moment of your life?
• Do you believe in God?
• How have you experienced God (or a Higher Power) in your life?
• Do you believe in the after-life? What do you think it will be like?
• When you meet God, what do you want to say?
• Have there been moments that tested your faith? What were those challenges and how did they impact your faith?

Serious Illness

• Can you tell me about your illness?
• Do you think about dying? Are you scared?
• How do you imagine your death?
• Do you believe in an after-life?
• Do you regret anything?
• Do you look at your life differently now than before you were diagnosed?
• Do you have any last wishes?
• If you were to give advice to me or others in our family, what would it be?
• What have you learned from life? The most important things?
• Has this illness changed you? What have you learned?
• How do you want to be remembered?

Family Heritage

• Where are your parents’ families from?
• Have you ever been there? What was that experience like?
• What traditions have been passed down in your family?
• Who were your favorite relatives?
• Do you remember any of the stories they used to tell you?
• What are the classic family stories? Jokes? Songs?

Military

• When were you drafted or when did you enlist?
• What do you remember about the day you enlisted?
• How did you tell your family and friends that you were joining the military? Are there any conversations that stand out from that time?
• If you enlisted, what were some of the reasons that you joined the military? How did you choose your branch of service?
• How did you imagine military life before you joined? How did your perceptions change after serving?
• What was basic training like?
• Can you describe a funny moment from your time in the military?
• What are some of the things you remember about adapting to military life?
• Where did you serve during the war?
• If you deployed overseas, how did you tell your loved ones you were being deployed?
• How did you stay in touch with family and friends back home?
• What are some things you remember most about your deployment?
• If you saw multiple deployments, how did they differ from each other? How did you change?
• Can you describe how you felt coming home from combat?
• Was there anything you especially missed about civilian life?
• Is there someone you served with that you remember fondly? Can you tell me about them?
• What are some fun things you and your friends did together while you were deployed?
• Did any of your military friends play pranks on each other? Can you describe a funny one?
• Did you ever get caught breaking any rules? Did you ever get away with something you weren’t supposed to do?
• Did you ever learn something about a fellow service member that surprised you?
• When did you leave the military? What was that process like?
• What were your first few months out of the service like?
• Was there anything or anyone that helped you during the transition from military to civilian life?
• Do you have advice for others transitioning out of the military?
• How do you think your time in the military affected you?
• What did you learn about yourself?
• What are some of your hopes for the future?
• What phrase or word will never be the same now that you served?
• When you were first discharged, what are some things about civilians that were difficult for you to deal with?
• Is there anything you wish civilians understood about military service?
• What are some habits you developed in the service that you like? What are some that you dislike?
• What are some things you miss about being in the service? What are some you are glad to have left behind?
• What has been difficult to communicate to family and friends about your military service?
• Do you have advice for other military couples?
• If you have children, what do you want them to know about your military service?
• Remembering the Fallen: What was your relationship to _______?
• Remembering the Fallen: Tell me about _______.
• Remembering the Fallen: What did _______ look like?
• Remembering the Fallen: What is one of your favorite memories of _______?
• Remembering the Fallen: How did you find out about _______’s death?
• Remembering the Fallen: What has helped you most in your grief?
• Remembering the Fallen: Do you have any traditions to honor _______?
• Remembering the Fallen: Do you have any funny stories about the two of you together?

Remembering a Loved One

• What was your relationship to _____?
• Tell me about _____.
• What is your first memory of _____?
• What is your best memory of _____?
• What is your most vivid memory of _____?
• What did _____ mean to you?
• Are you comfortable/ can you talk about _____’s death? How did _____ die?
• What has been the hardest thing about losing _____?
• What would you ask _____ if _____ were here today?
• What do you miss most about _____?
• How do you think _____ would want to be remembered?
• Can you talk about the biggest obstacles _____ overcame in life?
• Was there anything you and _____ disagreed about, fought over, or experienced some conflict around?
• What about _____ makes you smile?
• What was your relationship like?
• What did _____ look like?
• Did you have any favorite jokes _____ used to tell?
• Do you have any stories you want to share about _____?
• What were _____’s hopes and dreams for the future?
• Is there something about _____ that you think no one else knows?
• How are you different now than you were before you lost _____?
• What is the image of _____ that persists?
• Do you have any traditions to honor _____?
• What has helped you the most in your grief?
• What are the hardest times?

Justice

• Tell me about the first time you were aware that the criminal justice system existed.
• Has your experience with the justice system changed you or your outlook? How?
• How has the criminal justice system affected your life?
• What do you wish others knew about the criminal justice system?
• Can you describe how you were arrested?
• How did your family and friends find out you were going to jail?
• What was jail like? Can you describe what it looked, smelled and sounded like?
• How did you communicate with people outside?
• Do you remember how you felt at the time when you were convicted? How did it change you?
• Tell me about the day you were released.
• What do you wish someone had told you about re-entry?
• What have been the happiest moments since you were released?
• Do you feel free? Why or why not?
• Tell me about what helped/helps you keep going?
• If you could change one thing about the criminal justice system, what would it be?

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