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Interesting questions to ask when you want depth

40 interesting questions about changed minds, hidden expertise, places and people, and what comes next. Easy to answer, but rarely asked.

Keepsake · Family storytelling publisher Published Dec 21, 2025 Updated Oct 3, 2026

In this topic: Skills

Quick starters

Use these questions to spark an easy conversation.

  • What did you change your mind about this year, and what changed it?
  • What topic do you know more about than most people?
  • What was the last rabbit hole you fell down online?
  • Which job would you try for one year if money did not matter?
  • What piece of advice did you ignore and later wish you had taken?

All questions

40 questions. Choose the ones that suit your conversation.

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Conversation guide

These 40 interesting questions ask about things people have noticed, learned or changed their minds about. They’re easy to answer and rarely asked, which is why the answers tend to surprise. Nothing here requires sharing a secret.

Picking a question

Choose a question you’d enjoy answering yourself, and be ready to go first. They work best one at a time, with room for a tangent, rather than as a rapid-fire round.

The second group, “What you know,” is often the best place to start. Most people have a subject they know more about than anyone else in the room, and they rarely get asked about it. It might be a job they did for 30 years or a hobby nobody else in the family shares. Give them the floor.

With older relatives

Questions 29 and 30 lead naturally into family history. “What do you do differently from how your parents did it?” can open a story about a parent, a move or a way of life that has gone. If you want to keep it, our family interview guide explains how to follow up and record it.

For questions about where the world is going, try thought provoking questions. For questions that invite longer stories, see open ended questions.

Helpful follow-ups

  • How did you find that out?
  • What surprised you most?
  • Who else should I ask about that?
  • What would you tell someone just starting?

Frequently asked questions

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