Questions to Ask Your Elders
Questions for talking with older relatives, family friends and elders in your community or trade about the parts of their lives that do not come up at gatherings: work, money, mistakes, the people they lost, what they have changed their minds about, and what they would advise someone your age.
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The questions
Each question, and why to ask it
Where did you grow up, and what did the street look like then?
Why ask it
Concrete detail is easier to retrieve than reflection, so this warms up the conversation. It also tends to produce the incidental things, who lived next door, what the shops sold, that no family record keeps.
What did your parents do for a living?
Why ask it
Occupations locate a family in its class and place, and one generation back is usually the furthest anyone in the family still knows with confidence. Ask what the work involved day to day, not just the job title.
What was your first job, and what did it pay?
Why ask it
Wages fix a life in its era better than dates do, and most people remember their first pay packet exactly. The answer often carries the hours, the boss, and the reason they left.
What did you and your friends do on a Saturday when you were young?
Why ask it
Leisure changes faster than work and gets recorded less. Expect specifics about dances, bicycles, cinemas, or long walks, and expect the answer to reveal how little money there was without you having to raise it.
What was the first big thing you bought with your own money?
Why ask it
Pride and thrift both surface here. Whether the answer is a coat, a motorbike, or a deposit tells you what mattered then, and how long it took to save is usually part of the story.
How did you meet the person you ended up with?
Why ask it
Phrased this way it does not assume a marriage, which matters when you are asking someone who was widowed early, never married, or had a partner the family never named. Almost everyone tells it readily, and the part worth pressing on is the first few weeks, which the polished family version skips.
What did people your age worry about that nobody worries about now?
Why ask it
This turns their era into evidence rather than nostalgia. Answers about illness, conscription, or losing a job with no safety net show you what daily risk felt like before the systems we take for granted existed.
Which historical event do you remember most clearly, and where were you?
Why ask it
The location anchors the memory and stops it becoming a general comment on the times. People often name something local rather than the famous event you were expecting, which is the more useful answer.
What did your parents insist on that you dropped with your own children?
Why ask it
Shows a generation deciding what to keep, which is more revealing than a list of traditions. It also gives them a way to criticise their upbringing without having to attack their parents directly.
What was the hardest year you have lived through?
Why ask it
Asking for one year rather than the hardest thing keeps it answerable. Expect bereavement, illness, or money, and expect the interesting part to be who helped and who did not.
When did you feel most out of your depth, and what did you do?
Why ask it
This gets at competence and improvisation rather than suffering. The good answers are practical, a first day, a business going under, a child in trouble, and they usually involve someone giving them a hand.
What did you get wrong about someone, and how long did it take to see it?
Why ask it
Invites a reassessment rather than a verdict, so it produces something more honest than asking about regrets. The delay is the revealing part, because people rarely admit how long they held a wrong opinion.
Was there a decision you nearly made that would have given you a different life?
Why ask it
The road not taken is usually more vivid than the road taken. Expect a job, a country, or a person, and expect them to be surprised how much of it they still remember.
What is the most useful thing anyone taught you about money?
Why ask it
Older generations often learned about money under conditions of scarcity, so the lesson tends to be concrete rather than theoretical. If the answer is a rule, ask what happened that made them adopt it.
Which friendship lasted longest, and what kept it going?
Why ask it
Long friendships survive on mundane maintenance, a weekly call, a shared routine, and this question gets at that rather than sentiment. Sometimes the answer is that the friendship ended, which is worth hearing too.
What do you know now about raising children that you did not know then?
Why ask it
Grandparents will often say things to a grandchild that they would never say to their own children. Keep it about knowledge rather than blame and you will get a more candid answer.
What have you changed your mind about?
Why ask it
A short question that resists an easy answer. It tends to draw out changes on religion, politics, or a family member, and the reason for the change matters more than the position they landed on.
Who did you lose that you still think about?
Why ask it
Grief that is decades old rarely gets an audience, and people are often glad of the chance. Do not rush to comfort them; the point is that the person gets named and described.
What do you still want to do?
Why ask it
Older people get asked about the past almost exclusively, which quietly treats their future as closed. The answer is sometimes small and entirely achievable, in which case you can do something about it.
Who else in the family should I ask about the parts you do not know?
Why ask it
Ends by pointing you somewhere. Every family has one person who holds the records and another who holds the stories, and this is how you find out which is which before it is too late.
What did you worry about at my age that turned out not to matter?
Why ask it
An easy opening that still returns something useful, since most people have a list ready. The answers tend to be about other people's opinions and timelines, which is exactly what someone in their twenties or thirties is least able to see.
What should I be worrying about that I probably am not?
Why ask it
This invites them to be direct, and many will have been waiting for the invitation. Take the answer seriously even if it stings, and ask what they would do about it in your position rather than defending yourself.
How did you decide what to do with your life, or did it mostly decide for you?
Why ask it
Giving them the second option makes an honest answer possible. Many people had far less choice than the tidy version suggests, and hearing that a life can be assembled from accidents is more useful than hearing about a plan.
What is the best decision you ever made, and did you know it at the time?
Why ask it
The second half is the part worth listening to. If they did not know, ask what made them do it anyway, because that is closer to how decisions actually get made than any framework.
How do you make a decision when you do not have enough information?
Why ask it
Long experience usually produces a rough rule, such as choosing the reversible option or the one that keeps them able to walk away. Ask for the last time they used it, so you get the rule and a worked example.
How do you tell the difference between being afraid of something and knowing better?
Why ask it
This is the question people most often need answered and rarely ask outright. The signals they describe, physical or practical, are worth more than any principle about following your instincts.
Who did you go to for advice, and what made you trust them?
Why ask it
The criteria matter more than the names. Most people describe someone with no stake in the outcome, or someone who had made the same mistake, which tells you what kind of counsel to look for yourself.
How did you deal with a boss, or anyone with power over you, that you could not change?
Why ask it
This gets practical tactics rather than principles: what they documented, when they left, what they let pass. Note whether the strategy was endurance or exit, and ask what it cost either way.
What did you do after something you tried failed in front of everyone?
Why ask it
Public failure is what younger people fear most and hear about least. What matters is the mechanics of the months afterwards: who stayed, what they told people, how long it took to stop mattering.
What does staying with the same person for decades actually take?
Why ask it
Phrased as a practical question, this avoids the sentimental answer. Expect something unromantic about tolerance, separate interests, or getting through a bad two years, and listen for what they say they had to give up.
What is worth spending money on, and what never was?
Why ask it
Answers are concrete and easy to act on: tools, shoes, travel, a house closer to work, help in the house when the children were small. The regrets are usually about paying for status rather than about extravagance.
What did you stop apologising for as you got older?
Why ask it
It gets at what age actually gives people, which is rarely wisdom in the abstract and often permission. Expect something about saying no, leaving early, or not explaining themselves.
What in our family or community should not be forgotten, and who else still knows it?
Why ask it
The second half turns an answer into a task, because it identifies the last remaining sources. Write the names down, and ask what should be recorded first if there is only time for one thing.
What do you want to be asked about that nobody asks you?
Why ask it
Older people are frequently consulted only about the past or about health. This hands them the subject, and what they choose usually reveals a competence or a period of their life the family has stopped noticing.
If you could put one thing in my hands to carry on with, what would it be?
Why ask it
Keep it for the end. It can be answered with an object, a practice, or a piece of knowledge, and whichever they choose tells you what they think will survive them.
Talking with older relatives
Practical guidance for the conversation itself
Setting it up
Ask for a specific conversation
Do not try to do this in the middle of a family gathering. Say you want an hour to hear about a particular part of their life, and name the part. A defined subject is easier to agree to than a general request to reminisce.
Bring something physical
A photograph, a document, a map of where they lived. Objects produce more detail than open questions do, and they give a shy person somewhere to look.
Two or three questions, not the whole list
One good question with follow ups will fill an hour. Working through a list produces short answers and an atmosphere of being processed.
Follow ups that actually work
- What happened next?
- Who else was there?
- How old were you then?
- What did that cost, or what did you earn at the time?
- What did you think would happen?
- Silence. Four or five seconds of it usually gets you the second half of the answer.
Where it goes wrong
Arguing with the history
You will hear opinions you disagree with and accounts that contradict what you were told. Correcting them ends the conversation. You are collecting their version, and you can weigh it later.
Treating them as a source rather than a person
If every question is about the past, the conversation becomes an extraction. Ask what they are reading, what is annoying them this week, what they think of your situation.
Assuming there is time
People put this off for a better occasion. The better occasion often does not arrive, and health can change what is possible within months.
Recording without asking
Ask, and accept a refusal. If they say no, take notes afterwards from memory instead, and write down the phrases they used rather than a summary.