A curated collection
The questions worth
asking.
Not an interview guide. Not a checklist. These are questions organized by depth — because some conversations need to be earned, and some moments ask for courage.
Start here.
What's something you made with your hands that you're still proud of?
What was the best meal you ever ate, and where were you?
What did your parents call you when they weren't using your name?
What did a typical Sunday look like when you were young?
Who was your first real friend, and what happened to them?
What song takes you somewhere specific when you hear it?
The ones that take courage.
What do you want us to remember about you that we might forget?
Was there a time you were truly afraid, and what did you do?
Is there something you've never told anyone that you'd want someone to know?
What are you most proud of that no one ever recognized?
Is there anything you'd want to say to me that you've never found the right moment for?
What do you hope happens after you’re gone?
When they're ready to go deeper.
Was there a moment when your life could have gone a completely different direction?
What's something you believed when you were young that turned out to be wrong?
What did you want to be when you were a child, and what happened to that dream?
Who taught you the most important thing you know, and did they know they taught you?
What year of your life would you most want to revisit, and why?
What did you carry from your own parents — good or bad — that you didn't mean to?
Ready to begin?
You don't need to ask them all.
Just start with one.
There are no wrong questions. Only unasked ones.