The hardest part is usually starting. Once a conversation like this is underway, it tends to find its own momentum — one memory leads to another, a question you didn't plan turns out to be the one that opens everything up. But you need somewhere to begin.
These questions are not a script. They are starting points. Use the ones that feel right, leave the ones that don't, and follow wherever the answers lead.
Childhood and place
What do you remember first about where you grew up — a street, a smell, a particular view?
What was the house like? Who else lived there?
What did you do after school? Where did you go, who did you go with?
What was the neighbourhood like — the people, the atmosphere, the things that happened there?
Was there a place that felt particularly yours when you were young?
What did the seasons feel like where you grew up?
Family
Who were the most important people in your early life, apart from your parents?
What do you remember about your grandparents?
Were there family stories that got told and retold — things that happened before you were born that everyone knew about?
What was the atmosphere in the house like — was it quiet, busy, loud, serious, warm?
Was there anyone in the family who was talked about but not talked about, if you know what I mean?
Work and daily life
What was your first job? How did you get it?
What was the work like — the hours, the people, the physical reality of it?
What did a normal day look like in your twenties?
What did people do for enjoyment? What did you do?
What did money feel like — was there enough, was it tight, did it shape the choices you made?
Hard times
Were there periods that were particularly difficult — times when things felt uncertain or frightening?
How did people around you manage hardship? Was it talked about or carried quietly?
Was there something that happened that changed the direction of your life?
Objects and photographs
Is there an object you still have from your childhood or early life?
If you could keep one thing from that time, what would it be?
Are there photographs you could tell me about — people or places I wouldn't recognise?
Is there something that belonged to someone you lost that you've kept?
Looking back
What do you think was the best decision you ever made?
Is there something you wish you had done differently?
What do you want the people who come after you to know about your life?
What do you think shaped you most — a person, a place, an experience?
What are you most proud of?
A few things to keep in mind
Let silence sit. Not every pause needs filling. Some of the best answers come after a moment of quiet.
Follow the detail. If they mention a name, a place, an incident in passing, ask about it. The things mentioned lightly are often the things that matter most.
You don't need to cover everything. One good hour of honest conversation is worth more than an exhaustive questionnaire answered in a hurry.