Without context it's really hard to say, Stopdog. Do you feel comfortable giving more detail? It's kind of an inelegant expression though, what that unfortunate terminal preposition...

I think "meeting someone where they're at" suggests that you are mindful and accepting of their capacities, state of mind, understanding of their situation etc. For example, if you were severely depressed and socially anxious and barely getting out of bed to brush your teeth let alone leaving the house, it would be supremely unhelpful to have a T suggest that you join the Y and go to aerobics classes. Meeting you where you're at is understanding that you've accomplished something huge just by making the appointment and showing up.

Does that make any sense?