Forty years of working life disappears easily behind a single job title. "My father was in construction." Behind that sit the first day, the boss he never forgot, the decision whether or not to move for a job, and the morning he handed in his keys. The right questions about work and career bring that back, and it usually turns out to be about far more than work.

What you'll find here:

• Why working life is often the least documented part of a life story.
• Questions by stage: starting out, keeping going, and stopping.
• How to ask about work that was hard, or that ended badly.
• What to do when someone says there is nothing worth telling.

Why this part so often goes missing

For many people of that generation, work simply was not a topic of conversation. You did it, you did not complain about it, and something else began when you got home. As a result children often know what their parents did, but not what it was like.

That is exactly where the story sits. Someone describing their work is describing the time they lived in: how you found a job without the internet, a trade that no longer exists, a factory that is no longer standing. It is often the part where the history of a country and the history of a family meet.

Start in 5 minutes

1. Pick one stage, for example the very first job.
2. Choose 3 questions you could not answer about your parent yourself.
3. Find an unhurried moment, ideally with nothing scheduled straight after.

Start here: 3 questions to break the ice

Work is a safe subject to open with. These three almost always produce something.

1. What was your very first paid job, and what did it pay?
2. How did you get it?
3. What did you buy with your first wages?

How to keep it a conversation

Ask about a day, not a career

"What was your work like?" gets you "fine". "What did an ordinary Tuesday look like when you had just started there?" gets you a story. Specific beats summary every time.

Follow the people

Work is about colleagues, bosses and customers. The stories that stay with someone are almost never about the trade itself, but about who they did it with.

Include the uncomfortable parts

Redundancy, a business that failed, work left unfinished, a career that went differently than intended. That belongs in the story, and it is often told with relief once someone sees you are not there to judge.

Keep it from turning into an interview

We build a question plan around your parent's actual life, and after each conversation we write new follow-up questions based on what was really said. See how it works. There is more background in our guide on interviewing your parents.

Questions about starting out

1. What did you want to be when you were a child?
2. What was your first real job, and how old were you?
3. What did your first day look like? What did you not yet know?
4. Who taught you the trade?
5. Was there someone who believed in you before you believed in yourself?
6. What did you earn, and where did the money go?
7. How did you find work back then, through an advert, a contact, or knocking on doors?
8. Did it feel like you had a choice, or was it more or less decided for you?
9. What did you wear to work?
10. How did you get there every day?
11. What was the first thing you learned to do properly?
12. Did anyone take you under their wing?

Questions about the years that followed

1. Which decision changed the direction of your working life most?
2. Is there a job you turned down that you still think about?
3. What was the hardest year at work, and why?
4. Did you ever resign, or were you ever let go? How did that go?
5. Who was the best manager you had, and what made them good?
6. Who was the worst, and what did you learn from that?
7. What were you good at that people did not expect from you?
8. Did you ever have to do something at work you did not stand behind?
9. How did you combine the work with the family? What lost out?
10. Did your trade change over the years you did it?
11. Was there a day at work you have never forgotten?
12. Did you make friends there who stayed friends?
13. What was the most physically demanding part of the job?
14. Was there a point when you thought about doing something else entirely?
15. What did a good week look like?

Questions about stopping and looking back

1. What was your last working day like?
2. What did you miss straight away, and what not at all?
3. What are you proudest of, looking back?
4. What would you do differently if you could start again?
5. What did work teach you that you also used at home?
6. Did you keep in touch with anyone?
7. Is there something you built or made that still exists?
8. How did you fill the first months afterwards?
9. Did your idea of what work is worth change over time?
10. If you could give one piece of advice to someone starting out, what would it be?
11. What do you hope your children took from watching you work?

When someone says there is nothing to tell

On this subject, the most common answer is "I just did my job." That is almost never true. It usually means the question was too big.

Make the question smaller

Do not ask about the career, ask about one place, one year, one colleague. "What did it smell like in there?" often does more than "what was it like?".

Use something physical

An old payslip, a staff photograph, a certificate or a tool from the shed opens the conversation faster than any question can.

Record it, even when it sounds ordinary

What is unremarkable to the teller is a window onto a vanished world for a grandchild. Our guide on recording family interviews covers the practical side.

Related question lists

• 100 Questions to Ask Your Father
• 100+ Questions About Life Lessons and Values
• 100+ Questions About Childhood Memories