Questions to Ask a Senior
Questions for a long conversation with an older relative, neighbour or friend, arranged from easy recollection towards the things people rarely get asked. Includes guidance on recording, pacing and what to do when memory is uneven.
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The questions
Each question, and why to ask it
What did your street look like when you were ten?
Why ask it
Concrete detail is easier to retrieve than summary, so this gets a conversation moving where a question about their childhood in general would stall. Expect shops, neighbours and sounds, and expect one of them to lead somewhere you would never have asked about.
What was the first thing you bought with money you had earned?
Why ask it
Small enough to answer immediately and it usually carries a whole context: what the job was, what things cost, who disapproved. It also opens the subject of work without sounding like a formal interview.
What job have you done that barely exists now?
Why ask it
Switchboards, typing pools, film processing, cash offices. You get a description of vanished daily work, and the details are the kind that no longer appear anywhere in writing.
What did your parents expect you to become?
Why ask it
The gap between that expectation and what happened is where the interesting story sits. Some people followed it exactly and can tell you what it cost, which is a subject they are rarely invited to discuss.
What was the first big decision you made against everyone's advice?
Why ask it
Asks for a moment rather than a philosophy, so the answer has a date and a consequence in it. Whether they think it was right is a good follow-up, and the answer is often complicated.
How did you meet the person you spent the most years with?
Why ask it
Phrased to work whether that person was a spouse, a partner or a friend, and whether or not they are still alive. If the answer turns to loss, follow it rather than steering back to the story.
What did an ordinary Sunday look like when you were in your thirties?
Why ask it
Ordinary days are almost never recorded and disappear completely within two generations. You will get the meal, the radio, who visited, what was closed, and it dates their whole world more precisely than any big event.
What could a week's wages buy then?
Why ask it
Turns an abstraction into something comparable: rent, a coat, a week of food. It tends to produce exact figures, because people remember prices from their twenties with surprising accuracy.
What news event do you remember exactly where you were for?
Why ask it
You are asking for the room and the reaction rather than the event. The interesting part is usually who they were with and what they did afterwards, which is the part history books leave out.
What did people your age worry about that nobody worries about now?
Why ask it
Polio, conscription, a telegram, the cost of a phone call. It gives a genuine sense of how much has changed, and it is a rare question that treats them as a witness rather than a source of advice.
What have you changed your mind about since you were forty?
Why ask it
More revealing than asking for their beliefs, because it shows movement. Answers often concern religion, politics or how to raise children, and they usually come with the specific experience that caused the shift.
Who taught you something you still use?
Why ask it
The answer is frequently not a parent or a teacher but a foreman, a neighbour or an older colleague. Ask what exactly they taught, since the skill itself is often worth learning and easy to demonstrate.
What was the hardest year you have had?
Why ask it
Ask it once and leave space. If the answer stays brief, let it. What gets you the fuller account is the follow-up about what helped, which people are more willing to describe than the difficulty itself.
What can you do that hardly anyone knows how to do now?
Why ask it
Mending, preserving, reading a pattern, judging weather, working a machine that no longer exists. Asking to be shown rather than told is usually welcome, and it changes the visit from an interview into something shared.
What do you wish someone had told you at twenty-five?
Why ask it
Better than asking for general advice because it is anchored to an age they can picture. Notice whether the answer is about work, money or people, since that ordering tells you what they think mattered.
Is there someone you lost touch with who you still think about?
Why ask it
A quiet question that often produces the most feeling in the conversation. Sometimes it leads to a name that can still be found, and sometimes just to being able to say it out loud after decades.
What is easier now than it was at forty?
Why ask it
Cuts against the assumption that ageing is only loss, and most people have a real answer: less need for approval, clearer priorities, more patience. It is also a question they are almost never asked.
What do people assume about you now that is not true?
Why ask it
Expect something about capability, technology or being spoken to as though they were a child. Worth asking, and worth acting on afterwards, because the answer is usually about how they are treated rather than how they feel.
Is there anything you would want the family to know that you have never said?
Why ask it
Leave this until trust is established and accept whatever comes, including nothing. If something significant is said, ask whether they want it passed on, and to whom, rather than deciding that yourself.
What would you like done with the things that matter to you?
Why ask it
A practical question that families often avoid until it is urgent, and which most older people are relieved to be asked plainly. Keep it about objects and wishes: photographs, tools, a ring, who should have what.
What was your favorite way to spend a Saturday when you were young?
Why ask it
An easy start because it asks about pleasure rather than achievement. The details that come out, a bus fare, a dance hall, a lake, are usually the hooks for every other story of that period.
What meal from your childhood can you still taste?
Why ask it
More specific than asking about a favorite meal, and it usually produces the cook rather than just the dish. Ask whether anyone still makes it, because that is often where the family history sits.
What were you listening to when you were twenty?
Why ask it
Music from late adolescence stays vivid when much else has faded, so this often works even when recent memory is unreliable. Playing one of the songs afterwards is a good use of the next visit.
What was your first job, and what did it pay?
Why ask it
The number is the good part. People remember their first wage exactly, and saying it out loud tends to lead straight into who hired them, what the work was like, and what they bought with it.
What tradition from your childhood have you kept?
Why ask it
Distinguishes what they chose to carry forward from what was simply done to them. If they mention something that has quietly stopped, you may have found something worth restarting.
What story does your family always make you tell?
Why ask it
Everyone has a well-worn story, and letting them tell the polished version relaxes them before you ask anything harder. Ask what happened afterwards, since that part is usually left out.
What was your favorite decade, and what was going on in your life then?
Why ask it
The second half stops it becoming a comment on history. Most people choose the decade they had the most freedom, and hearing why tells you what they still miss.
What's the biggest change you've watched happen?
Why ask it
Listen for whether they name technology or something about how people treat each other. The second kind of answer is harder to get elsewhere, and it usually comes with a specific example rather than a generalization.
Was there a moment when your life could easily have gone another way?
Why ask it
This gets at the near miss: the job not taken, the letter that arrived late, the person they almost married. It is often the story they have thought about most and been asked about least.
What are you proud of that hardly anyone knows about?
Why ask it
Public accomplishments have been repeated until they are flat. This asks for the one that was never celebrated, often a debt quietly paid, someone helped, a habit broken, and it is usually the answer they are most glad to give.
What do you look for in a friend now that you didn't care about at thirty?
Why ask it
Puts a comparison in the question so the answer has to be specific. People who have outlived friends often talk about reliability and simple presence rather than shared interests.
What are you still trying to get better at?
Why ask it
Assumes they are still working on something, which is a small kindness in itself. Answers range from a language to patience with a family member, and either gives you something to ask about next time.
What do you wish younger people understood about getting older?
Why ask it
Expect something plainer than inspiration: the boredom, the paperwork, being talked over, the surprise of still feeling like yourself. Resist the urge to soften it, and just let them finish.
How to have the conversation
Practical guidance for the conversation itself
Setting it up
Ask before you record, and say why
A phone on the table is fine if you have asked. Say that you want the grandchildren to hear it in their voice. Most people agree, and the recording matters more than you expect within a few years.
Sit somewhere quiet, side by side
A television or a busy cafe makes hearing hard work, and hard work makes answers short. Sitting alongside rather than opposite also removes the interview feeling, which is the main thing that shuts these conversations down.
Bring something physical
Photographs, a map of the old neighbourhood, an object from the house. Recall attaches to objects far better than to questions, and a single photograph will often produce twenty minutes you could not have prompted.
Plan for an hour, expect three visits
Long sessions tire everyone and the best material usually arrives once the questions have stopped feeling like a list. Two shorter conversations produce more than one marathon.
While you are talking
- Ask about a specific year or age rather than a period. Anchored questions get detailed answers.
- Follow the digression. The story they wander into is usually better than the question you had planned.
- Let silences run. Older recollection often surfaces after several seconds, and filling the gap loses it.
- Ask what something cost, smelled like or sounded like. Sensory detail unlocks memory that summary does not.
- Write down names and places phonetically as you go, and check the spellings at the end.
- Notice fatigue and stop before it. Ending while they are still enjoying it is what makes a second conversation possible.
When memory is uneven
Stay with the distant past
Where recent memory has faded, early memory often remains clear and accessible. Childhood, first jobs and songs are usually easier ground than what happened last week, and they are no less worth recording.
Do not correct dates or details
Correcting produces embarrassment and shortens the conversation. If accuracy matters for a family record, check it separately afterwards against documents rather than in the room.
Avoid questions that test
Do you remember who I am, or asking them to recall a name on demand, puts them on the spot. Offer the information instead and carry on: it was lovely to see Anne last week, works better than asking whether they remember Anne.
Follow the feeling rather than the facts
If an account is muddled but clearly matters to them, respond to what it meant instead of untangling it. The point of the visit is the contact, and the record is secondary.
What to avoid
Raised voices and simplified language
Speak clearly and face them rather than loudly. Shouting distorts speech and makes it harder to follow, and simplified vocabulary is heard as condescension by someone whose hearing, not their mind, is the issue.
Treating the conversation as extraction
Working down a list without offering anything of your own turns a visit into an interview. Answer some of your own questions, and be prepared to talk about your life too.
Pushing past a closed door
A war, a lost child, a marriage that ended. If an answer is short, take it as final for today. Coming back to it months later, once, is reasonable. Pressing in the moment is not.
Losing the recording
Copy the file somewhere else the same day and note the date and who is speaking. Recordings that exist only on one phone tend to disappear with the phone.