Tonight with your 9 to 12 year old
The prompt
“Was there ever a time you had the perfect chance to brag and chose not to?”
What to listen for
If they can recall this, it shows a maturing sense of quiet confidence, they're learning that they don't need to announce their wins to feel good about them, which is a real marker of inner security.
Listen for whether holding back felt easy or like a real effort, if it was hard, they deserve to hear that you noticed the restraint, since it's a genuinely tough thing to do at this age.
If they say they always brag when they get the chance, respond with curiosity rather than correction, ask what bragging gets them, since that usually points to a need to feel noticed that can be met in other ways too.
What this tells you
This shows whether their confidence is starting to come from within, rather than needing constant outside proof.