
Challenge 38 · 21 days
Ask One More Question
Go deeper. Build real connections.
“Curiosity builds connection.”
Why this challenge
Most people listen while preparing their own response.
One additional question forces you to become curious about what another person is actually saying instead of immediately turning the conversation back toward yourself.
What you do
During every meaningful conversation:
Ask one sincere follow-up question before talking about yourself.
Listen completely.
Do not interrupt.
Before you begin
Curiosity turns ordinary conversations into extraordinary connections.
Keywords
- Curiosity builds connection.
- Better conversations. A kinder world.
The point
- During every meaningful conversation:
- Ask one sincere follow-up question before talking about yourself.
- Listen completely.
- Do not interrupt.
- Ask questions that open, not close. Truly listen to the answer. Don’t interrupt.

Your record
Where this stands
The tracker is the record. Writing on a day checks that day in. Mark the challenge completed when you finished it, or not continuing when you are done with it. Those marks are the review on your map. The lines under a day are here for whatever you want to say.
21 days
21 days. Open a day to write it. Writing checks that day in.
Day 1
In your own words
This space is here for the day the other lines do not fit. Write it the way you would say it. Add a picture if that is closer. It stays with this day, and it stays on your map.