Yourtale
Start a free session →

Questions to ask your grandfather about his life

A sequenced set of questions to ask your grandfather about his life, built around the years only he remembers, plus how to run a sitting he can get through and record what he says before it is gone.

By The Yourtale team · Published 20 September 2026 · 10 min read

The best questions to ask your grandfather are the ones only he can answer. Ask what the ordinary world looked like before you existed, what his work was when work was physical, who he was before he was anyone's grandfather, and what he wants kept. Ask a few, let each answer run, and record it.

This is not another list of two hundred questions. It is a smaller, sequenced set built for one specific conversation: a grandchild sitting down with a grandfather who is a generation further back than a parent, and who is therefore the last living witness to things nobody else in the room can describe. We interview people for a living. The grandfather interview has one large advantage and three practical problems, and this page is mostly about those.

Key takeaways

  • Work out his birth year before you write a single question. A man born in 1938 and a man born in 1952 lived through two different versions of ordinary life, and the questions that open one will bore the other.
  • He will often tell a grandchild what he never told his own children. The generational distance takes the defensiveness out of the room, which is why this is the most productive family interview there is.
  • Ask about the world, not just the life. He is a primary source on work, money, food, travel, and Sundays as they actually were. Nobody else can answer those questions after he is gone.
  • Plan a 45 to 60-minute sitting, not 90 minutes, and plan several of them. Stamina, hearing, and energy set the length, and the third sitting is usually the best one.
  • Record it. The memory of the conversation fades within days. StoryCorps and the Library of Congress American Folklife Center archive personal interviews for exactly this reason.

Why do most lists of questions to ask your grandfather fall flat?

Search for questions to ask your grandfather and you get the same page every time. A hundred questions, two hundred, sorted into tidy categories, with no guidance on which to ask first or how long to let an answer run.

The problem is arithmetic. A good question takes seven to ten minutes to answer properly, once you count the pauses and the side memories. A hundred questions would mean stopping your grandfather after one sentence each. That is not an interview, it is a form.

The second problem is that the lists are generic by design. They have to work for everybody's grandfather, so they ask "what was your childhood like" and get "fine, we didn't have much" in return. A question that could be asked of any man produces an answer that could have come from any man. The questions that work are the ones that could only be asked of him, and you can only write those once you know roughly when and where he was young.

Where should you start? Do the arithmetic on his birth year

This is the step almost everyone skips, and it is the one that changes the whole conversation.

Work out the year he was born. Then work out how old he was during four or five events he would actually remember standing somewhere for. A grandfather who is 78 in 2026 was born in 1948 and was twenty in 1968. A grandfather who is 88 was born in 1938 and was a small child through the Second World War, old enough to remember the rationing and the fear in the adults but not the politics. A grandfather who is 95 was born in 1931 and remembers a house without a telephone.

Then write your questions around where he was standing, not around the event. Not "what do you remember about the war" but "who was in the house with you, and what were the adults not telling you". Not "what was the sixties like" but "what did you and your friends do on a Friday night in 1968, and what did it cost".

There is a good reason to weight your questions toward his youth. People recall the years between roughly ten and thirty more readily than any other stretch of life. Memory researchers call it the reminiscence bump, and a systematic review of the evidence calls it one of the most robust findings in autobiographical memory. A question about 1965 will almost always get more out of him than a question about 2015.

What questions should you actually ask your grandfather?

This is a working set, not a script. It runs from easy to harder. Pick six to eight for a first sitting, let them branch, and keep the rest for next time. The point is not to finish the list. It is to get him going and then stay out of the way.

His childhood and the house (warm-up, pick two):

  1. Describe the house you grew up in. Where did people sit in the evening, and what was making noise in the room?
  2. What did your family eat in a normal week, and what did you eat when there was money?
  3. What did you do with a whole Saturday when you were ten?
  4. Who in the family was considered difficult, and what had they done?

The world that is gone (pick two):

  1. What did you do every week as a young man that nobody does now?
  2. What did a town look like on a Sunday when you were twenty?
  3. When did the house get its first telephone, television, or car, and what changed after it arrived?
  4. What did people your age argue about that nobody argues about anymore?

Work and money (pick two):

  1. What was your first real job, what did it pay, and what did the first wage go to?
  2. Describe a normal working day at the job you did longest. Start from when you woke up.
  3. What could you do with your hands that you would struggle to teach anyone now?
  4. Was there a job or a move you turned down that you still think about?

Service, if it applies (pick one or two):

  1. Where were you sent, how old were you, and who did you go with?
  2. What did you write home about, and what did you leave out?
  3. What do you remember about the first day back?

Love and marriage (pick two):

  1. How did you meet Grandma, and what did you think of her before you knew her?
  2. What was the first year of marriage actually like, in the flat or the house you had then?
  3. What did the two of you disagree about for forty years and never resolve?
  4. Who did you love before that, who we have never heard about?

Being a father, being a grandfather (pick two):

  1. What kind of father do you think you were, honestly?
  2. What did you not have time for when your children were small that you think about now?
  3. What is different about being a grandfather than being a father?

Beliefs and lessons (pick two):

  1. What did you believe at twenty-five that you no longer believe?
  2. What is the worst decision you ever made, and what did it cost you?
  3. What do you know about getting old that nobody tells you beforehand?

Legacy (always close here):

  1. What would you want a great-grandchild who never meets you to know about who you actually were?

Close every sitting on that last one. The answer is usually the most quotable line of the whole conversation, and it lifts the mood before you stop recording. For a wider pool to pick from, StoryCorps Great Questions is the best free library we know, and the Library of Congress Veterans History Project sample questions are worth reading even if he never served, because they are unusually good at asking about ordinary days. If you want a tighter set built around one focused sitting, we put together the best memoir interview questions for a 90-minute conversation, and if you are interviewing both grandparents together, questions to ask your grandparents is the longer list.

Why will he tell you things he never told his own children?

This is the advantage, and it is worth knowing about before you start.

A father talking to his own son or daughter is still, in some part of his head, managing the job. He does not want to be judged for the years he was short-tempered, or to explain a decision his children lived through the consequences of. So he gives facts instead of feelings, which is the trap we wrote about in questions to ask your dad about his life.

A grandchild is outside all of that. You were not there. You are not owed an explanation, you are not keeping score, and he can tell you the story as a story. We have sat in interviews where a man talked for forty minutes to a granddaughter about a bankruptcy his own children had only ever heard referred to as "the bad year". He was not hiding it. Nobody had ever asked him from outside the argument.

Two things follow. First, ask the hard questions. You have more room than his children do, and he is often relieved that someone finally wants the real version. Second, if your parent is in the room, the room changes. Consider interviewing him alone, and let your parent listen to the recording afterwards.

How do you run a sitting he can actually get through?

Here are the three practical problems, and what we do about them.

Stamina. Plan 45 to 60 minutes, not ninety, and plan three or four sittings rather than one long one. Agree the length before you start. The Oral History Association's best practices advise that both parties "agree in advance to the approximate length of each interview session", and it matters more here than anywhere: a grandfather who is tiring will start giving short answers, and you will read it as him closing down when he is just worn out. Morning is usually better than afternoon. Stop while he still has something left, because the next sitting is the one that gets good.

Hearing. Sit face on, in the same room, with the television off and no music. Do not shout the question. Ask it slowly and in short sentences, and be willing to rephrase rather than repeat at volume. Phone calls and video calls lose most of what makes this work, so travel to him if you can.

Repetition. He has five stories he tells at every family gathering, and you are about to get all five. Do not steer around them. Those five are the ones he has decided matter, and you have never actually recorded them properly. Then go inside the story for the part he has never told: not the story of the crossing, but what he was carrying, who he sat next to, what he was frightened of. The familiar story is a door if you ask about its details rather than its plot.

Two more rules that hold for every family interview. Do not correct him. He will tell a version of events you remember differently, and the recording is his memory, not the family's official record. And if he does not want to go somewhere, do not push. The Baylor Institute for Oral History builds its guidance around drawing out the narrator's own account rather than keeping the conversation moving, and the Oral History Association is explicit that a narrator has the right to refuse a subject. Move on, and come back another day if at all.

What should you ask your grandfather before it is too late?

If he is frail or his memory is going, the temptation is to save the big questions for a moment that feels right. That moment tends not to arrive, and the questions get harder to ask the longer you wait. Ask the legacy questions in the first sitting, not the last.

They are not morbid. They are the answers you will want in your own hands later: what he is proudest of, what he wants said about him, what he hopes the family carries on, and the plain factual things nobody asks until they cannot. Ask him the story behind one object he would want kept, and write down which object it is. Ask him to name the people in the photographs while he still can, because an unlabelled box of faces is the single most common thing families are left holding. Ask what he knows now that he wishes he had known at your age.

If he served in the military, there is one more thing worth doing. The Library of Congress Veterans History Project accepts interviews recorded by family members and friends aged 15 or over, from veterans of any branch and rank who served at any point since the First World War, and loved ones of veterans who have died may submit their first-person accounts. The interview you were going to record anyway can end up in a national collection. We wrote a fuller guide to recording a veteran's war stories and military service.

The window is shorter than it looks, and the stories disappear faster than most families expect. If you want a plan rather than a question list, we wrote one: interview your grandparents before it is too late.

How do you record the answers so they are not lost?

This is the part most families skip. They have the conversation, it is wonderful, and then it evaporates. You remember that it mattered. You do not remember the exact words, the way he said the name of the street, or the laugh.

Record the audio. The voice memo app on your phone is enough to start. Put the phone on a folded cloth rather than a hard table, so you do not get the knock of every cup. Say the date, his full name, and where you are into the recording before you ask the first question, because in twenty years that ten seconds will be worth more than you think. Back it up the same day to a cloud account or an external drive, because one lost phone is one lost grandfather's voice.

Then get a rough transcript with Whisper, MacWhisper, Otter, or a paid service, so the words become text you can edit into a chapter. The voice itself is worth keeping on its own terms, and we wrote separately about keeping a grandparent's actual voice in the book. If you would rather hand the recordings to an institution, FamilySearch Memories accepts personal oral histories at no charge.

Three recorded sittings of an hour each, transcribed, is enough for a real book about his life. You do not need a hundred questions. You need a handful of good ones, a recorder running, and the patience to sit through the silences.

How our service does this

We run these interviews for families who would rather not run them alone. An AI interviewer talks with your grandfather in sittings of 60 to 90 minutes, or shorter if that suits him better, follows the structure above, asks the branching follow-ups, and waits through the pauses. It then drafts chapters from the transcripts, which your family reads and edits before anything is printed into a hardcover book. You are the editor. Nobody on our team reads his story unless you ask us to help.

We are honest that the interviewer is AI, not a person. That is the reason it is patient and always available. Your grandfather can talk on a Tuesday morning or late at night, across as many sittings as he wants, without anyone's calendar in the way, and it will never sigh at the fifth telling of the same story. It is an interviewer with a finite job, producing a book. It is not a companion, and we would not describe it as one.

We are not right for everyone. If your grandfather would rather be interviewed by a grandchild he knows, that is a better conversation than ours, and the questions on this page are yours to use. What matters more than who asks them is that someone does, and that the answers are recorded before they slip away.

Frequently asked questions

What are good questions to ask your grandfather about his life? The best ones are the questions only he can answer. Ask him to describe the house he grew up in and where people sat in the evening, what his first real job paid and what the first wage went to, what a town looked like on a Sunday when he was twenty, and what he believed at twenty-five that he no longer believes. Close with what he would want a great-grandchild who never meets him to know about who he actually was. Work out his birth year first, so the questions land on years he genuinely remembers.

How is interviewing a grandfather different from interviewing your dad? The distance helps. A father talking to his own child is still managing the role, so he gives facts instead of feelings. A grandchild is outside the argument, was not there for the decisions, and is not keeping score, so grandfathers often tell a grandchild things their own children never heard. The trade is practical rather than emotional: shorter sittings, hearing, and the five familiar stories he tells at every family gathering.

How long should a sitting with my grandfather be? Plan 45 to 60 minutes rather than 90, and plan three or four sittings instead of one. Agree the length before you start, sit face on with the television off, and stop while he still has energy left. The third conversation is usually the best one, because by then he has stopped performing and knows you actually want the details.

What should I ask my grandfather before he dies? Ask the legacy questions early rather than saving them. What he is proudest of, what he wants said about him, what he hopes the family carries on, and the story behind one object he would want kept. Then do the plain factual work while he can still do it: sit with the photographs and have him name the people in them. An unlabelled box of faces is the most common thing families are left holding.

Should I record the conversation with my grandfather? Yes. The memory of a conversation fades within days, including the exact words and the sound of his voice. Record it on your phone, state the date and his full name at the start, back it up the same day, and run a rough transcript through Whisper, MacWhisper, or Otter so the words become text you can edit into a chapter. Three recorded hours are enough for a real book about his life.

Sources cited above