Questions to Ask Elders
Questions for a younger person seeking guidance from an elder, whether a grandparent, a community elder, or someone two generations ahead in the same trade. They ask for particular judgements rather than general advice: decisions made, money learned the hard way, minds changed, and knowledge that will leave with them.
The questions
Open any question for the note
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.
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.
What did you learn about money the hard way?
Why ask it
Older people are usually willing to be specific here in a way they are not about income. Expect debt, a guarantee signed for a relative, a house bought or not bought, or a pension left too late.
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.
How did you keep friendships going through the years when you had no time?
Why ask it
Ask specifically about the busy decades, because that is where most friendships are lost. The answers are usually mundane and repeatable, such as a standing arrangement nobody had to organise.
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 did you get wrong as a parent that you would warn me about?
Why ask it
This is one of the few questions that reliably gets past a generation's reticence, because it is framed as help rather than confession. Do not reassure them too quickly, and do not use the answer against them later.
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.
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.
What have you changed your mind about?
Why ask it
It asks for a revision rather than a conviction, which produces a specific story instead of a position. Someone who cannot name anything is telling you how much weight to give the rest of their advice.
What did you inherit from your family that you had to unlearn?
Why ask it
This separates the parts of a tradition they chose from the parts they were handed. It is also the most useful question if you suspect you are repeating something and cannot see it.
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.
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 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.
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.
Asking an elder for guidance
Practical guidance for the conversation itself
Asking well
Bring a real situation, not a general question
Asking how to handle a difficult colleague gets a proverb. Describing the colleague, what was said, and what you are considering doing gets judgement. Elders with real experience are far better at cases than at principles.
Ask what they did, not what you should do
The past tense is easier to answer honestly and harder to get wrong. It also spares them the position of being responsible for your decision, which is why some people give bland advice.
Say why you are asking them specifically
Naming the reason, that they have run a business, raised four children, or come through the same illness, marks the conversation as serious. Vague requests for wisdom get vague answers.
Ask about protocol if there is any
In some families, communities, and cultures, approaching an elder has expectations attached, about who introduces you, when to visit, whether to bring something, and what may be recorded. Ask someone closer to them before you arrive rather than guessing.
While they are talking
- Let a pause run. The first answer is often the polite one and the second is the real one.
- Ask when it happened and who else was involved. Detail is what makes advice usable later.
- Do not argue with the framing, even when the language is dated. Take the substance and let the wording go.
- Write down what they said afterwards, in their words. Advice that is only remembered as a gist stops being useful within a week.
- Ask permission before recording, and again before sharing any of it with other relatives.
Pitfalls
- Do not treat one person as the voice of their whole generation or community. They will usually say so themselves if you leave room.
- Do not ask only about the past. People consulted purely as historical sources tend to withdraw from the present conversation.
- Avoid asking for approval when you have already decided. If your mind is made up, say so and ask what to watch out for instead.
- Do not press a closed subject. War, migration, a lost child, or an estrangement may be off limits, and the rest of the conversation depends on you accepting that quickly.
- Do not promise to act on advice you will not take. Saying you will think about it is both true and enough.
Making it worth their while
- Come back and tell them what you did and how it went. Almost nobody does this, and it is the thing most likely to keep the door open.
- Offer something practical in return: a lift, help with a device or a form, an afternoon of work in the garden.
- Bring them into a decision more than once. Being consulted repeatedly means something different from being interviewed once.
- Pass on what you were told, with attribution, to the people it would help. Say who said it.