It is one of the finest questions you can ask anyone, and one of the hardest to get answered. Asked exactly as it stands here, it usually produces a silence and then something general. This page is about how to get it answered, and why it is worth continuing to try.

What you'll find here:

• Why the question rarely works asked head-on.
• Twelve ways to ask it so that an answer does come.
• What to do with an answer that is too short or too tidy.
• Why you should ask it more than once.

Why the question so often stalls

"What lesson do you want to pass on?" asks someone to summarise in one sentence what eighty years taught them, and to phrase it solemnly as well. Almost nobody can do that on the spot. What comes back is "just be honest" or "work hard", and there is nothing wrong with that, but it is not the story.

The story sits underneath: which event taught them that, who from, and what it cost them. That is what to ask about, not the summary.

How to ask it so it lands

1. Ask about a moment, not a lesson.
2. Ask about somebody else: who taught you that?
3. Ask it more than once, spread across several conversations.

Twelve ways to ask the same question

Each version below asks essentially the same thing, through an opening that is easier to answer.

1. What would you want your grandchildren to remember about you?
2. What advice were you given that you never forgot?
3. What did your own father or mother do that you ended up doing too?
4. What do you regret understanding too late?
5. What would you say to yourself at twenty?
6. Which mistake do you hope we do not make?
7. What turned out to matter more than you thought at the time?
8. And what turned out to matter far less?
9. When were you most satisfied with how you handled something?
10. What did you always stand by, even when it was inconvenient?
11. What would you want said about you?
12. If you could pass on only one thing, what would it be?

What to do with a short answer

Ask about the event behind it

After "be honest" comes: "when did you notice that mattered?" There is almost always a story there, and often one you have never heard.

Ask who taught them

Life lessons rarely come from nowhere. Usually there is a person, and that person is a chapter of their own.

Ask about the time it did not hold

"Was there ever a time you could not stick to that?" That turns a tidy answer into an honest story, and people tell it more readily than you would expect.

Keep it from turning into an interview

We build a question plan around your family and write new follow-up questions after each conversation, based on what was actually said. See how it works. See also our guide on interviewing your parents.

Ask it more than once

This is the only question on our pages we recommend repeating. The answer changes, and that is not a contradiction; it is the point.

The first time you mostly get what someone thinks is expected of them. After a few conversations, once a good deal has been told, something more personal arrives. And at the end of a project, once someone has heard their own story come back to them, there is sometimes a third answer that is neither of the first two.

All three belong in the book. Together they show how someone came to look at their own life.

What to do with the answer

Record it, even when it is short. With this question especially, how something is said is half the meaning: the hesitation before, the small laugh after. Our guide on recording family interviews covers capturing that simply.

Related question lists

• 100+ Questions About Life Lessons and Values
• Thoughtful Questions About Pride and Milestones
• Questions to Ask When Talking Is Hard