60 Questions to Ask Your Grandparents, and How to Turn the Answers Into a Book

What makes a good question to ask a grandparent?

The questions that get stories are open (they can't be answered yes or no) and specific (they point at a place, a person or a moment). 'Were you happy as a child?' gets 'Oh, yes.' 'What did you do on Saturday mornings when you were ten?' gets twenty minutes and a story you've never heard.

The real magic is in the follow-up. When an answer opens a door, walk through it: 'What happened next?' 'What did she say?' 'How did that feel?' 'Do you remember what you were wearing?' One good question with three follow-ups beats ten questions in a row.

The 60 questions below are grouped by chapter of life, which is also how you'll organize the book later. Don't ask them all at once. Pick five or six per visit.

What questions should you ask about childhood and family?

Start here. Early memories are often vivid, and they're a gentle way into the conversation.

1. Where were you born, and what's the first thing you remember about that place?
2. Describe the house you grew up in, room by room.
3. What did your street or neighborhood sound and smell like?
4. What were your parents like? What did each of them do all day?
5. Who else lived with you or visited often?
6. What did your family eat on an ordinary weeknight? On a holiday?
7. What games did you play, and with whom?
8. What were you scolded for most as a child?
9. Which grandparent or relative did you feel closest to, and why?
10. What family stories were told over and over when you were small?
11. What did you want to be when you grew up?

What questions should you ask about school, work and making a living?

Work fills most of an adult life, and it's where many of the best stories hide.

1. What was your school like? Who was your favorite teacher?
2. What were you good at, and what did you struggle with?
3. What was your first paid job, and what did you do with the money?
4. How did you end up in the work you did for most of your life?
5. Describe a normal workday from the moment you woke up.
6. Who was the best boss you ever had? The worst?
7. What's something you were proud of at work that nobody noticed?
8. Was there a job you wanted but didn't get, or a road you didn't take?
9. How much did things cost when you started working: rent, bread, a car?
10. If you could do one year of your working life over, which would it be?

What questions should you ask about love, marriage and friendship?

Let them decide how much to share. Some of the best answers here are funny.

1. How did you meet Grandma (or Grandpa)? What was your first impression?
2. What was your first date? Where did you go?
3. How did the proposal happen, and who said yes first?
4. What was your wedding day like? What went wrong?
5. What was the hardest part of the first year together?
6. What did you argue about most, and how did you make up?
7. Who was your best friend when you were young? What happened to them?
8. What was it like when your first child was born?
9. What did you learn about love that you wish you'd known sooner?
10. Is there anyone you lost touch with that you still think about?

What questions should you ask about hard times?

These questions need care. Ask them later in a conversation, or on a later visit, once trust is built. Always make it easy to say 'I'd rather not talk about that.'

1. What was the hardest year of your life?
2. Was there a time when money was really tight? How did you manage?
3. What big historical events did you live through, and how did they touch your family?
4. Did you ever have to leave a home, a town or a country? What did you take with you?
5. Who did you lose too early, and what do you remember most about them?
6. Were you ever seriously ill or injured? Who looked after you?
7. What's a mistake you made that taught you something?
8. Was there a time you were really afraid?
9. Who helped you through the hardest times?
10. What got you through when things felt impossible?

What questions should you ask about values, faith and change?

These open up who they are, not just what happened to them.

1. What did your parents believe in most strongly?
2. What role did faith or religion play in your life?
3. What's something you changed your mind about as you got older?
4. What's the biggest difference between the world now and when you were young?
5. What do you think is better now? What's worse?
6. What traditions do you hope the family keeps?
7. What's a rule you lived by?
8. Who did you most admire, and why?
9. What makes a person good, in your opinion?
10. What are you most proud of?

What questions should you ask about advice and legacy?

Save these for the end. Answers here often become the last chapter of the book.

1. What advice would you give your 20-year-old self?
2. What do you want your grandchildren to know about you?
3. What's the best decision you ever made?
4. What do you wish you'd spent more time on? Less?
5. Is there a story you've never told anyone in the family?
6. What recipe, song or saying should never be forgotten?
7. How would you like to be remembered?
8. If you wrote a letter to a great-grandchild you'll never meet, what would it say?
9. Is there anything you'd like to ask me?

How do you run the conversation?

A good interview feels like a visit, not a test. Plan for 30–60 minutes at a time; older people can tire quickly, and a second visit is a gift, not a failure.

• Ask permission to record, and use your own phone's voice recorder. It frees you to listen instead of scribbling.
• Bring photos. A picture of a house or a wedding unlocks memories no question can.
• Pick one theme per visit: childhood today, work next week.
• Let silence sit. The best stories often come after a long pause.
• Don't correct dates or details in the moment. Note them and check later.
• Write down names, places and years as they come up; you'll need the spelling later.
• Write up your notes the same day, while the tone of voice is still in your head.
• End on something light, and thank them. You're asking for something precious.

How do you turn the answers into a book?

Transcribe or summarize each conversation, then sort the stories into life chapters: the same groups as the questions above work well. Each chapter needs one or two full stories, not every fact. Keep their words where you can; 'We didn't have two nickels to rub together' is worth more than any paraphrase. Show them each chapter before it's final. They'll correct things and often remember more.

When you're ready to draft, the Novelleo app (iOS and Android) can help. Choose "My own story" (it covers life and family stories), answer a few questions about whose story it is, and Novelleo sets up a title, the people in the story and a 4–20 chapter plan. You bring the interview notes; the AI drafts each chapter with you, and you edit every line so it sounds like them. Novelleo doesn't record or interview anyone; the conversations are yours. Export the finished book as a PDF or Word file and print copies at any print shop you like.