Six questions, ranked by how heavy they land. Start where you can. The gentle ones are not lesser — they earn the harder ones later.
Or write your own
The hardest question is rarely on a list. If you already know yours, write it here.
Step 3 of 4 · Before you go in
Four things to know walking in.
Optional. Thirty seconds each. It's easier to ask a hard question if you've already thought about what happens after it.
Where will you be?
A car ride. The porch. After dinner. Not in front of a screen.
What if they cry?
Plan for it now so you don't flinch then.
What if you cry?
It's allowed. But know in advance whether you keep going.
What's your exit ramp?
If it gets too heavy, how do you wind down without changing the subject?
Step 4 of 4 · After
After you had it.
Come back to this once you've sat with them. Speak it while it's fresh. Their exact words, not your summary. Use the mic — you're not going to type this on the drive home.
What they said
listening…
Gawande · the question behind
That wasn't right. Stay with what they said — their words are the work.
What surprised you
End Notes
For —
The question I asked
What they said
What surprised me
Now keep going.
You earned the next question. The gentle ones open the door for the hard ones — but only if you walk through. Schedule one more sit-down in the next month. Bring this card.
If they said something you want to remember exactly, write it on paper. The kind they could leave on their fridge. Show them you heard.
Where this comes from. Atul Gawande's Being Mortal argues that the question that opens up end-of-life conversations isn't "what are you afraid of?" — it's "what do you want, if time gets short?" The Conversation Project (theconversationproject.org) builds whole guides around the same idea. The frame here: start gentle, earn the harder ones, write down what they said while you can still ask them to clarify.