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Complete Family Interview Guide

Questions to Ask Family Members

Family stories disappear within one generation. Here are 640+ questions to help you capture them before it's too late.

640+ Questions
8 Life Themes
7 Holidays
8 Milestones

The Universal Top 10

If you only ask 10 questions, ask these. They work for parents, grandparents, or any family member to spark meaningful stories.

1What is your earliest memory?
2How did you meet your spouse/partner?
3What was your first job and what did you do with your first paycheck?
4Who was the most influential person in your life outside of family?
5What is the bravest thing you’ve ever done?
6What family tradition do you hope we keep forever?
7What was the happiest moment of your life?
8What is the hardest lesson you’ve had to learn?
9How do you want people to remember you?
10If you could give your younger self one piece of advice, what would it be?

Why These Questions Matter

Your family's stories are disappearing. Every day, memories fade. Every year, the people who remember your family's history get older. The conversations you don't have now won't be possible later.

The regret we hear most often is simple: "I should have asked more questions when I had the chance."

Research shows that 90 percent of grandchildren don't know their grandparents' life stories. Telloom created this guide from our experience conducting hundreds of professional family interviews. Every question prompts real stories, not just one-word answers.

Find the Right Questions

By Relationship

Parents, grandparents, siblings

By Life Theme

8 themes, 50+ topics

By Holiday

Thanksgiving, Christmas, more

By Life Milestone

Retirement, wedding, birthday

Questions by Relationship

Tailored questions to honor the specific role they play in your life. Click each relationship to see questions.

For Your Parents

Your parents are the bridge to your own history

What's your earliest memory?
What was your fondest childhood memory?
How did you choose my name?
What was I like as a baby?
Tell me about your parents (my grandparents) - what were they like?
How did you meet mom/dad?
What surprised you most about being a parent?
How did you choose your career, and what did you enjoy about it?
What's a childhood lesson that has stayed with you into adulthood?
What values did your parents give you that you still remember?
What was a typical day like for you as a child?
What were your favorite meals or foods as a child?
What advice would you give to me about parenting?
What do you want me to remember most about you?
What family traditions do you hold most dear, and how did they start?
See all Parent Questions Questions for Mom Questions for Dad Questions for Elderly Parents

For Your Grandparents

They remember things nobody else can tell you

What is your fondest childhood memory, and why does it stand out?
Describe the home where you were born or grew up
What was a typical day like for you as a child?
Tell me about your parents (my great-grandparents) - what were they like?
How did you meet grandma/grandpa?
What was your first job? What did you learn from it? How much did you make?
What historical events had the biggest impact on your life?
What was it like raising my mom/dad?
What family traditions did your grandparents pass down to you?
Where did our family originally come from?
What's the most significant change you've seen in your lifetime?
What values do you hope to pass on to future generations?
What were your aspirations as a child, and how did they evolve?
What childhood game or activity did you love most?
What do you want our family to remember about you?
See all Grandparent Questions Questions for Grandma Questions for Grandpa

For Your Siblings

Share memories and see your childhood through their eyes

What's your earliest memory of us together?
What was your fondest memory from our childhood?
How would you describe what it was like growing up in our family?
What's something I did as a kid that you remember clearly?
What did you want to be when you grew up?
How do you think we're similar and different?
What's your favorite memory with me?
What family tradition meant the most to you growing up?
How would you describe our parents to someone who didn't know them?
What childhood lesson has stuck with you into adulthood?
Questions for Brother Questions for Sister

Questions by Life Theme

Explore specific chapters of a life story. Telloom organizes over 640 questions into these 8 key themes. Click each theme to see topics and sample questions.

Personal History

Childhood, family relationships, marriage, and parenting stories

Topics in this theme

HomesYour Basic InformationYour ChildhoodYour Children and ParenthoodYour FriendshipsYour GrandchildrenYour GrandparentsYour Marriage and LoveYour ParentsYour PetsYour Siblings

Sample questions

Tell me about your grandchildren. Describe each of them, their personalities, and your relationship with them.
Can you recall a special moment or event that brought your family closer together?
What role do your sibling(s) play in your adult life?
How did you meet your spouse or significant other, and what initially attracted you to them?
What has been the key to maintaining a strong and healthy relationship in your marriage?
Can you share a time when you and your spouse faced a significant challenge together and how it affected your relationship?
What did you get in trouble for that your parents never found out about?
Can you list the homes you've lived in and the approximate dates or your age when you lived in them?
When you think about your children's future, what do you most hope for them?

Values & Beliefs

Legacy, reflections, spirituality, and life wisdom

Topics in this theme

Legacy and Future GenerationsLife ReflectionsMoney and FinancePersonal ReflectionsSpirituality and Faith

Sample questions

In what moments or times have you experienced the most beauty in life?
What have you learned about people and humanity? What do you believe about people in general?
What is a lesson you've learned that you want to pass on to the next generation?
Is there something you regret not doing?
How do you balance the desire to enjoy life now with the need to save for the future?
What was one of your proudest personal moments? Why?
In what ways have your views on death and dying evolved over your lifetime?
How do you find comfort or strength in your spiritual beliefs during challenging times?

Career & Education

Work, learning, entrepreneurship, and professional life

Topics in this theme

Career and Professional LifeEducationEntrepreneurshipMilitary ServiceTeam ManagementTechnology and InnovationVolunteering and Philanthropy

Sample questions

What have you found most effective in managing a team while also influencing those you report to?
How do you identify and capitalize on market opportunities in your industry?
What was the key motivation behind starting your own business, and how has that vision evolved?
What are the joys and challenges you faced in your career, and how did you overcome the challenges?
Reflecting on your career, is there anything you would have done differently with the benefit of hindsight?
Looking back, what advice would you give to yourself at the start of your entrepreneurial journey?
How do you stay motivated and engaged in your work, especially during challenging times?
What was the most impactful lesson you learned in school, and how has it influenced your life?

Hobbies & Interests

Creativity, music, sports, nature, and books

Topics in this theme

Creativity and ArtGardening and Green SpacesHobbies and InterestsLiterature and BooksMovies and TelevisionMusic ListeningMusic PlayingOutdoor Adventures and NatureScienceWatching Sports

Sample questions

Can you recall a book that completely changed your perspective or opened your mind to new ideas?
What's your favorite memory of spending time in your garden or green space?
How have your musical tastes and playing style evolved over the years?
Have you ever attended a major sporting event? What was the experience like?
Can you share an experience where your hobby connected you with others or your community?
What did you love to do as a kid, before high school?
Have you ever been inspired to explore a new interest or hobby because of a movie or TV show?
What is your most memorable camping or hiking experience?

Life Experiences

Milestones, challenges, travel, and meaningful moments

Topics in this theme

HistoryLaughter and Light MomentsLife Milestones and AchievementsLocal CommunityTravel and Experiences

Sample questions

How do you balance individuality with a sense of community and belonging?
Can you share a memorable community event you participated in and its significance?
What's the first major news story you remember from your childhood?
What's a silly tradition you've shared with friends or family over the years?
Where all have you traveled, and which places left the biggest impression on you?
What's a joke, prank, or inside joke that still makes you smile years later?
Is there a particular place you've visited that changed your perspective or outlook on life?
What is one travel experience that you feel everyone should have at least once in their lifetime?

Cultural & Heritage

Traditions, family history, and cultural identity

Topics in this theme

Cultural Identity and HeritageFamily HistoryFamily MigrationFamily Traditions

Sample questions

In what ways do you actively engage with or contribute to the preservation of your cultural heritage?
How do you balance maintaining family traditions with the individuality and personal preferences of family members?
How do family traditions reflect or honor your ancestors or family history?
What role do food and meals play in your family traditions?
If you migrated from somewhere else, what motivated your decision to leave your home country or hometown?
Are there any significant historical events that your ancestors were part of or witnessed?
Are there any traditions you've started or wish to start with your own family? What inspired them?
Are you a first-generation immigrant? Can you share the story of your family's migration?

Health & Wellbeing

Personal growth, resilience, and physical health

Topics in this theme

Challenges and Overcoming AdversityPersonal GrowthSports and Physical Activity

Sample questions

Who has been a pivotal figure in your personal growth journey, and in what ways have they influenced you?
Can you discuss a failure or setback you've experienced and the lessons it taught you?
Can you share one of your favorite pieces of advice you've received?
Have you ever had to make a tough decision that involved significant risks? How did you decide?
How do you stay healthy physically and mentally today? How has that evolved from when you were younger?
How have you adapted to unexpected changes or disruptions in your life or career?
Can you describe a habit or practice you've adopted that significantly contributes to your personal growth?
Can you share a memorable moment or achievement related to sports or physical activity?

Food & Culinary

Recipes, meals, cooking traditions, and culinary experiences

Topics in this theme

Cooking and BakingDiet and NutritionFood and Culinary Experiences

Sample questions

Do you have a favorite restaurant or food spot that you always recommend? What makes it special?
What's the most adventurous dish you've ever tried, and would you eat it again?
How do you approach maintaining a balanced diet, and what does that look like for you?
What are your most memorable food experiences or favorite meals, and when did they take place?
In what ways do you involve others in cooking, whether teaching or cooking together?
What's your approach to experimenting with new recipes or ingredients?
Can you discuss a baking tradition in your family or culture that you cherish?
What is one of your favorite family recipes?

Questions by Holiday

Holidays bring families together. These questions turn small talk into real conversations worth remembering.

Thanksgiving

Questions about gratitude, family gatherings, and giving thanks

What Thanksgiving tradition from your childhood do you wish we still did today?
Who was always in charge of cooking the turkey, and what made their method special?
What are you most grateful for this year that you weren't grateful for ten years ago?
Tell me about a Thanksgiving when something unexpected happened - good or bad.
What dish would Thanksgiving not be complete without in our family?
Who was the first person to host Thanksgiving in our family, and what was it like?
What's a Thanksgiving memory that still makes you laugh?
If you could invite anyone, living or passed, to our Thanksgiving table, who would it be and why?

Christmas

Questions about holiday memories, gift-giving, and faith traditions

What's your earliest Christmas memory?
What was the most memorable gift you ever received as a child?
How did your family celebrate Christmas when you were growing up?
What Christmas tradition do you hope our family keeps forever?
Tell me about a Christmas when times were hard but you still found joy.
What was the best gift you ever gave someone, and why was it meaningful?
How has the meaning of Christmas changed for you over the years?
What holiday song instantly takes you back to your childhood?
More Christmas Questions

Hanukkah

Questions about traditions, family celebrations, and heritage

What Hanukkah traditions did your family observe when you were young?
Who taught you to play dreidel, and what stakes did you play for?
What's your favorite memory of lighting the menorah together as a family?
How has the way you celebrate Hanukkah changed over the generations?
What traditional food was everyone's favorite during Hanukkah in your home?
Tell me about a Hanukkah gift that really surprised you.
What does the miracle of Hanukkah mean to you personally?
How do you hope we'll continue celebrating Hanukkah in the future?

Easter

Questions about spring traditions, faith, and family meals

What Easter traditions did your family have when you were growing up?
Tell me about the best Easter egg hunt you can remember.
What was Easter Sunday like in your childhood home?
Who made the Easter meal, and what was always on the table?
How has the meaning of Easter evolved for you over your lifetime?
What's your favorite springtime memory from childhood?
Did your family have any unique Easter traditions that others might find surprising?
What Easter memory would you most want our family to recreate?

New Year's

Questions about resolutions, reflections, and fresh starts

What's the best New Year's Eve you can remember, and what made it special?
Did you ever make a New Year's resolution that actually changed your life?
How did your family celebrate the New Year when you were young?
What year stands out as one of the best years of your life, and why?
What hopes do you have for our family in the coming year?
What tradition did you start in a new year that became permanent?
Looking back, what year would you like to relive and why?
What advice would you give to someone starting a new chapter in their life?
More New Year's Questions

Fourth of July

Questions about patriotism, summer gatherings, and family memories

What's your favorite Fourth of July memory from childhood?
Where did your family watch fireworks when you were growing up?
What did Independence Day mean to your parents or grandparents?
Tell me about a summer cookout or picnic that stands out in your memory.
What American tradition or value means the most to you and why?
Did anyone in our family serve in the military? What do you know about their service?
What's the most patriotic moment you've ever experienced?
How has your understanding of what it means to be American changed over time?

Memorial Day

Questions about honoring service members and family veterans

Do we have family members who served in the military? What do you know about them?
How did your family observe Memorial Day when you were growing up?
Is there a veteran in our family whose story you think should be preserved?
What sacrifices have family members made for our country?
Tell me about visiting a veteran's grave or memorial. What did it mean to you?
What lessons did you learn from family members who served?
How do you think we should honor those who gave their lives for our freedom?
What stories about military service were passed down in our family?

Pro tip: The best holiday conversations happen naturally. Don't interview—just ask one question and let the stories flow. Record on your phone so you can be fully present in the moment.

Questions by Life Milestone

Life's big moments come with reflection. A retirement party, a graduation, a new baby: these questions help capture what people are thinking and feeling during major transitions.

Retirement

Questions about career reflections, future plans, and life wisdom

What are you most proud of from your career?
What do you wish you had known when you started your career?
How did you know it was time to retire?
What do you look forward to most about this next chapter?
What will you miss about working, if anything?
What advice would you give to someone just starting out in your profession?
Looking back, would you have chosen a different career path?
What's the first thing you want to do now that you have more time?
How do you hope to spend your time in retirement?
Retirement Party Questions

Graduation

Questions about education journeys, dreams, and advice

What does this graduation mean to you?
Who helped you get to this point, and how would you thank them?
What was the hardest part of your educational journey?
What's the most valuable lesson you learned outside the classroom?
What dreams do you have for your future?
What advice would you give to someone just starting their education?
Which teacher or professor had the biggest impact on you, and why?
What would you tell your younger self about the importance of education?
How do you hope to use what you've learned to make a difference?

Wedding

Questions about love stories, marriage advice, and family traditions

How did you know they were 'the one'?
What's your best piece of advice for a happy marriage?
Tell me about your wedding day - what moment stands out most?
What wedding traditions are important to carry forward in our family?
What surprised you most about marriage in the first year?
How do you keep the romance alive after many years together?
What do you love most about your partner that you didn't expect?
What challenges have you overcome together that made you stronger?
What do you hope for the newlyweds' future?

Anniversary

Questions about relationship wisdom and favorite memories

What's the secret to staying happily married for so many years?
What's your favorite memory from your years together?
How has your relationship changed and grown over time?
What do you appreciate about your partner now that you didn't in the beginning?
What's been the biggest adventure you've shared?
How do you handle disagreements in a way that keeps you close?
What tradition do you share that keeps your relationship strong?
What would you tell a young couple about the realities of long-term love?
What moment are you most grateful you shared together?

Milestone Birthday

Questions about life reflections and wisdom gained

What does reaching this age mean to you?
What do you know now that you wish you'd known at 20?
What has been the best decade of your life so far, and why?
What accomplishment are you most proud of?
What would you tell your younger self if you could?
How have your priorities changed over the years?
What's on your bucket list that you still want to do?
What life lesson took you the longest to learn?
What brings you the most joy at this stage of life?

New Baby

Questions about parenthood advice and family hopes

What advice would you give to new parents?
What do you remember most about when I was a baby?
What values do you hope we'll pass on to the new baby?
What was the biggest surprise about becoming a parent?
What family traditions do you hope we'll continue with this child?
What's one thing you wish you'd known before becoming a parent?
How did having children change your perspective on life?
What do you hope this child's life will be like?
What stories about our family do you want this baby to hear someday?

Empty Nest

Questions about parenting reflections and the next chapter

How does it feel now that the kids have grown and moved out?
What do you miss most about having children at home?
What are you most proud of about how you raised your children?
What would you do differently if you could parent again?
How are you planning to fill your time now?
What's the best part of this new chapter of life?
What advice would you give to parents whose children are about to leave?
How has your relationship with your spouse changed since the kids left?
What do you hope your relationship with your adult children will look like?

Moving / New Home

Questions about places, memories, and new beginnings

What will you miss most about the home you're leaving?
What's your favorite memory in this house?
What made you decide to move?
What are you most excited about in the new place?
How many homes have you lived in, and which was your favorite?
What makes a house feel like a home to you?
What traditions do you want to bring to the new home?
Is there a room or space in our old home that holds special meaning?
What do you hope the new home will bring for our family?

Why milestones matter: These transitional moments are when people are most reflective. A retiring parent has decades of wisdom. A bride or groom is thinking deeply about family and the future. Capture these insights while they're fresh.

The Art of the Interview

How to move from "Q&A" to "Real Conversation."

Do This

  • Ask "Tell me more." The best stories come from the follow-up.
  • Embrace silence. Wait 3 seconds after they finish speaking. They often have more to say.
  • Start easy. Ask about hobbies or pets before diving into deep life lessons.

Avoid This

  • ×Yes/No questions. Instead of "Did you like school?", ask "What was your favorite part of school?"
  • ×Interrupting. Let them finish their thought, even if they wander.
  • ×Strict scripts. If a story goes in a new direction, follow it.

Troubleshooting Conversations

If they say...It might mean...Try asking...
"They say 'I don't remember'"The question is too broad (e.g., 'Tell me about your childhood').Get specific. Ask about the kitchen in their childhood home, their favorite toy, or the smell of their school.
"They get emotional or cry"You've touched on a meaningful or painful memory.Pause. Offer a tissue. Don't rush to change the subject. Say 'Take your time.' Emotion means the story matters.
"They give one-word answers"Asking Yes/No questions (e.g., 'Did you like school?').Switch to 'How' or 'Why'. 'How did you feel on your first day of school?' or 'Tell me more about that.'
"They ramble or go off-topic"Natural conversational flow.Let them wander a bit—that's where gold is found. Gently guide them back later: 'I want to hear more about [X] you mentioned...'

Don't Just Ask. Preserve.

Asking the questions is step one. Saving the answers is step two. Telloom makes it easy to record, organize, and keep these stories safe forever.

Guided Recording

The app prompts you with these exact questions while you record, so you never get stuck.

Searchable Transcripts

We automatically type out every word, so you can search for "Grandma's apple pie" later.

Read our Recording Guide Hire a Professional Interviewer

Start Your Family's Story Today

You have the questions. Now you just need to start. Download our conversation starter kit or book a call to let us handle the heavy lifting.

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Written by the Telloom Production Team

The questions in this guide have been refined through hundreds of hours of professional oral history interviews. We update this list annually to include new topics like digital legacy and modern family dynamics.

Questions to Ask Family Members: Complete Guide | Telloom