Tonight with your 13 to 17 year old
The prompt
“What's it like for you being the new person somewhere, like a class, a team, a group?”
What to listen for
If they describe strategies they use, finding one person, watching before jumping in, they've built real confidence in navigating unfamiliar situations, which means they trust themselves socially even when it's uncomfortable.
If they describe it as dreadful or paralyzing, resist minimizing it with "everyone feels that way", instead let them know that feeling is normal and that it's okay to take time to find their footing.
A short "it's awkward but fine" is a totally reasonable answer, not everything needs to be a big reveal.
What this tells you
How they handle being new somewhere shows you how secure they feel about belonging before they've proven themselves to anyone.