This is no longer a problem, as he has moved on and I have retired, but I still don't know how it could/should have been handled. I'll write it in the present tense, though.
My employer in the Emergency Department (who is also a family friend) will give me a back-handed compliment several times a year. They seem to come out of the blue and always take me by surprise. They usually take the "I don't know why, but..." form. Examples:
I don't know why, but that patient had a lot of nice things to say about you.
I don't know why, but they really want you to volunteer there again.
I don't know why, but they were very impressed with you and want you to go back (when I did a stint for the hospital filling in for a doctor in one of their satellite offices.)
His daughter was our babysitter. Out of the blue, he said,
I don't know why, but Alice really respects you, and looks up to you as a role model.
These comments hurt me personally and leave me confused. In my defense, I am considered to be a very good doctor; the nurses ask for me when they or their family members are sick, and the Nursing Supervisor told my boss - I don't know under what circumstances - that she thought I was an outstanding clinician and made the most challenging diagnoses. I don't get many complaints of any kind. We have monthly meetings for quality assurance feedback (missed diagnoses, inappropriate treatment, patient complaints, etc.) and semi-annual one-on-one evaluations which go well.
He also does praise my work occasionally, though, and often asks my opinion on difficult cases when we happen to have overlapping shifts.
I don't know what to say. Usually my responses are,
-Why are you saying that?
-Is there something I should know?
I did tell him that phrasing things that way puzzled me and that I thought it was hurtful. He doesn't seem to understand what the problem is. He denies that the phrasing is awkward or subject to a negative interpretation.
What is the best way to handle a boss's back-handed compliment that hurts?