The harder questions

Failure, contradiction, the things not said. Ask late, and only if you have earned it.

4 questions. There is no order you have to follow.

• Tell me about a failure that hurt — and what you took from it.
• On what did you significantly change your mind over the course of your life?
• What did you give up for something else? Did you have a choice?
• Is there something you feel two things about at the same time — both love and hate?

Using these

There are harder questions than these, about shame, despair and regret, and they belong in a private conversation, not on a public page. What is here is enough to start with, and stopping is always the right answer if the room changes.

Asking about someone, rather than asking them

If the person is not here to answer, the same question has to change shape. “Where did you grow up?” is a cruel thing to ask about someone who has died, so each question also has a second wording, for asking someone who knew them.

• Share a failure that hurt them — and what they took from it.
• On what did they significantly change their mind over the course of their life?
• What did they give up for something else? Did they have a choice?
• Was there something they felt two things about at the same time — both love and hate?

The other themes

• Who they are: The questions that get past what someone did for a living.
• How they speak: Turns of phrase, filler words, how they open a conversation — the texture most interviews never ask about.
• Memories: Specific moments, not summaries of a decade.
• Personality: How they handle change, order, other people, and themselves.
• Relationships: The people who shaped them, and how they talked about them.
• Values and beliefs: What they thought was worth doing, and why.
• Objects, songs and places: A photograph, a piece of music, a room — the fastest routes into a story.
• Everyday life: What an ordinary day actually looks like. The detail that vanishes first.