I am a Certified Life Coach, Child Advocate and mentor. I work with the Rabbis in my community and with the at-risk population. I ask questions when necessary and stay away from Loshon Horah, not everything is everyone’s business.
If someone were to ask me straight out, I would have some questions as well:
Why are you asking me this?
Is something wrong with your child?
Did someone tell you something?
What are you afraid of?
Why is this a concern of yours?
And of course I would want to know who they are, who there Rav is, etc.