Questions to ask your mentor

27 questions to ask your mentor about hard times

Ask these late, in person, once, and with the door open to decline. Handled well they produce the chapter the book turns on. Tell them what they taught you before you ask anything. Then ask who taught it to them. The chain goes back further than either of you expects.

How to use this list. Ask by voice and record it. One or two questions a visit is plenty; the follow-up ("Who else was there?" "What did she say?" "What happened the day after?") matters more than the next question. The 17 marked tender come last: ask them once, late, in person, with "or would you rather leave that?" in the question.

1. Was there a year when everything changed? What was the first sign?Turning points are the spine of any book. Ask how it started, not just what happened.
2. What was the proudest moment of your working life? And the worst day?
3. Did you ever quit something, or get fired? What did you tell people?
4. What did money mean in your house? Who held it, and what did "we can't afford it" sound like?
5. What was rationed, scarce, or impossible to get, and how did people manage?
6. What did the first winter, the first job, the first apartment look like?
7. What did you eat when there was no money?
8. What was still rationed, broken or unrebuilt in your town when you were growing up?
9. Were there power cuts, strikes or petrol queues where you lived? What did you do during one?A candlelit evening is a scene; "the seventies were hard" is not.
10. Was there a holiday that was cancelled, missed, or spent somewhere strange? What happened?
11. Was there a time you nearly left, or nearly lost them?tender
12. Was there a moment your faith was tested?tender
13. What was the hardest year of your life, and what got you through it?tender
14. Who showed up for you when it mattered? Who didn't?tender
15. Is there a loss you still carry?tender
16. What did you learn about yourself from the worst thing that happened to you?tender
17. Was there a time you were truly afraid?tender
18. Was there a death, a birth or an illness that changed what you believe?tender
19. Did you ever have to leave a house you loved? What was the last thing you did before you shut the door?tender
20. Who was the bully, and who stood up to them?tender
21. Was there a time you could not pay for something you needed? What did you do that week?tender
22. Which journey did you take because you had to, not because you wanted to?tender
23. Did you ever have to put an animal down, or give one away? Who did it, and who cried?tender
24. Was there a friendship that ended badly? What would you say to them now?tender
25. Who turned up at the hospital, the funeral or the door without being asked?tenderThe unasked arrival is the clearest proof of a friendship the book will get.
26. Was there polio, TB or another illness that everyone was afraid of? Did it touch your street?tender
27. What should a person do in the week after something terrible happens? What did you do?tender

What these questions are for

A good book about a person needs more than facts. It needs the person on the page: how they talked, what they wanted, what they did when it mattered, the story that shows them. These questions cover 10 of the things a writer needs about your mentor: the story that shows them, wants, fears and wounds, contradictions, beliefs and values, habits, routines and work, their place in history, objects, places, food, music, loss and fate, key relationships, how others saw them.

More questions to ask your mentor

• All questions to ask your mentor
• Questions to ask your mentor about their work
• Questions to ask your mentor that are funny
• Questions to ask your mentor for their advice
• Questions to ask your mentor about what they want remembered
• Questions to ask your mentor that go deep
• Questions to ask your mentor for a quick conversation
• Questions to ask your mentor about money and getting by
• Questions to ask your mentor about friendship

Or see questions for everyone else, and how to interview a parent about their life.