There's no single right way to begin. The best approach depends entirely on the person you're talking to: their personality, their comfort with being the centre of attention, and how much they know about what you're trying to do.
The most important thing is to read them first.
Some people love being asked
Some people are natural storytellers. They light up when someone sits down and says "tell me about when you were young." They've been waiting for someone to ask. With these people, you can be direct: pull out a prompt, ask the question, and get out of the way. They'll do the rest.
Some people need a gentler entry point
Others find being asked about their life slightly uncomfortable. They might feel self-conscious, or they genuinely don't think their stories are interesting enough to share. A direct question can make them clam up before they've even begun.
For these people, the conversation works better when it doesn't feel like a conversation. Start somewhere ordinary: what's for dinner, what the kids have been up to, something that happened during the week. Let the small talk run for a while. Then when the moment feels right, slip in a gentle hook: "Do you remember when we used to go to...?" or "Whatever happened to so-and-so? She used to make the best cakes."
You're not asking them to tell a story. You're just leaving a door open. And often, they'll walk right through it.
The environment matters more than you think
Wherever possible, choose a setting that feels natural and unhurried. The kitchen table, a long drive, a walk, a quiet afternoon at home. These are the places where people relax into conversation without realising it.
Avoid settings that feel formal or staged. If someone sits down and thinks "this is an interview," they'll perform rather than remember. The goal is for them to forget there's any particular purpose to the conversation at all.
You don't have to tell them you're recording
If you think knowing they're being recorded will make your loved one self-conscious or reluctant, then don't record them. Just have the conversation. Record a voice note yourself afterwards while everything is still fresh: what they said, the details, the moments that made you laugh or stopped you in your tracks.
Some of the richest recordings come from exactly this kind of natural, unguarded conversation.
Fill in the blanks for them
One of the most effective techniques is to half-remember something yourself and let them correct you. "Wasn't it Auntie someone who used to make that dish, what was her name?" People love filling in gaps. It feels less like being asked and more like being helpful.
You're not interviewing them. You're just remembering together.
A gentle reminder
There's no perfect moment and no perfect question. The conversation you have on an ordinary Tuesday afternoon, talking about nothing in particular, can turn into something you'll treasure forever.
Just start somewhere. The stories will find their own way out.