These questions can help you get beyond the familiar “What’s something you believed when you were my age that you don’t believe anymore?”
Your grandparent has probably changed their mind about more than a few things over the years. Maybe they swore they would never get married or that they’d stay in their hometown forever. Ask what they felt certain about at your age—and what eventually made them reconsider. The answer can make a younger person think, “Oh my God, you were my age,” says Mike O’Krent, founder of “What was your childhood like?” is an enormous question—the conversational equivalent of handing someone a blank book and asking them to fill it. It’s better to zoom in on one specific setting. “The dinner table is a window into an entire family, sometimes an entire childhood,” says Lauren Befus, founder of Every family has at least one expenditure it considers financially unhinged. Perhaps your grandparent’s parents refused to pay someone to repair anything they could conceivably fix themselves. Maybe restaurant meals, store-bought clothes, or long-distance phone calls were treated as scandalous extravagances. The question can reveal what money represented in your grandparent’s childhood home: security, freedom, status, or a source of constant stress. You might also recognize a few financial commandments that have traveled down the family line. Oh, that’s why your mom refuses to pay for shipping or regards full-price cereal as a personal affront! Your grandparent wasn’t always the person reminding everyone to be careful. Once upon a time, they might have sneaked somewhere forbidden, played hooky from Sunday school to take a nap in the cornfields behind the church, concocted an impressive lie, or attempted to conceal a mishap from their parents.“Tell me about the dinner table in the house where you grew up.”
“What was considered a waste of money in your house?”
“Tell me about a time you got into trouble—and how you got out of it.”
“What object have you kept from childhood—and what’s its story?”
That battered book, recipe card, or piece of jewelry might look unremarkable. Then you hear the story about why it’s still a prized possession.
Keating recalls talking to a woman who had grown up poor and dreamed of owning a particular doll. When she received it for her birthday, she treasured it so deeply that she eventually passed it down through her family. “We attach relationships to objects,” Keating says. Eventually, “an object isn’t just a thing anymore.” It evokes a person, place, yearning, or moment someone wants to keep close.
“Who believed in you before you believed in yourself?”
The answer could introduce you to a teacher, mentor, neighbor, boss, or friend you’ve never heard about—yet whose encouragement altered the course of your family’s history.
For O’Krent, it was his third-grade teacher, Mrs. Glaze. One day, despite making him stay inside during recess because he couldn’t keep his mouth shut, she looked him in the eye and said: “You’re going to be somebody important someday.”
He never forgot it. An influential person isn’t always who you would expect, O’Krent says, and the best part of the story may emerge when you ask why your grandparent connected with them. What did they see in your grandparent—and how did their belief change what your grandparent saw in themselves?
“What decision did you make that everyone else thought was wrong?”
Maybe your grandparent pursued a career their family didn’t approve of, moved somewhere unexpected, ended—or began—a relationship, or took a risk everyone else considered foolish. Ask why people objected. Then borrow O’Krent’s favorite follow-up: “Do you agree with that?”
Your grandparent might still insist everyone else was wrong. Or perhaps the decision led directly to something they’d love to forget. “Everybody makes mistakes,” O’Krent says. What matters is “the lesson you learn from it.” Either way, you’ll discover how your grandparent responded when their judgment collided with other people’s expectations—and whether they’d make the same choice again.
“What are you proud of that would never appear on a résumé?”
Résumés are good for recording promotions and degrees. But they don’t capture the time someone took care of an aging parent, raised children through a miserable year, started over after a failure, repaired a relationship, or became the friend who always showed up.
“What are you still figuring out?”
There is, apparently, no birthday at which a person wakes up with life completely sorted out. Grandparents still have evolving identities, relationships, hopes, and uncertainties, says Claudia Johnson, a licensed marriage and family therapist in Seattle.
Asking what your grandparent is still figuring out communicates: “I don’t only want to know who you were. I’m interested in who you are now,” Johnson says. Maybe they’re learning how to enjoy retirement, trying to understand a changing friendship, or deciding what they want the next few years to look like.
Answer the question yourself, too. That reciprocity transforms the interaction from an interview into a real conversation—and reminds both of you that nobody ages out of uncertainty.
“If you were naming a baby today, what name would you choose?”
Not every meaningful question requires rummaging through the past. That’s especially important when you’re talking to someone with , a nonprofit that connects musicians with people living with dementia and other “If you could ask me anything right now, what would you want to know?”
After putting your grandparent in the hot seat, turn the interview over to them. What have they always wondered about you?
“The grandparent’s not expecting that one,” O’Krent says. That’s exactly why he likes it: The question gives your grandparent some control over where the conversation goes and makes the exchange feel mutual.
Once the conversation is flowing, don’t cling too tightly to your prepared questions. O’Krent teaches people an unusual listening trick: “The next thing you say has to include at least one word from the last sentence they say.” Because you don’t know when that last sentence is coming, you have no choice but to pay close attention. It might feel awkward at first, he acknowledges, but it helps the other person feel heard. Plus, the best question is almost always the follow-up you didn’t plan.
“What do you wish you’d asked your own parents or grandparents?”
The answers often involve what Keating calls “huge identity questions”: Where did I come from? Who am I? Why did my family’s life unfold the way it did? Most people know the milestones, she says, but what they really want is “the story behind everything.”
Listen closely. Your grandparent might be telling you not only what they regret leaving unanswered, but which parts of their own story they hope you won’t.