I think of my T as often asking questions along those lines.

I don't think there's any right answer to that particular question but I would imagine it would be beneficial to you to discuss with your T the way it made you feel.

From what you've said it doesn't feel to me like any judgement was passed. At least when my T asks something like this I think she is just asking me... to find the answer inside myself as to why I did or did not do something.

Often it's something I haven't stopped to question for a second and if my T hadn't stopped to question me on it I would not have realised why I have done (or not done) something.

With her help and through questions like this I sometimes gain more insight as to why I might have avoided doing something in particular (like telling a friend that I'm sad to hear that they are unwell and that I care).

I'm also not saying that's what you should do myself, but that maybe all your T meant was to see if there was any reason you had decided not to say something to your friend and whether that was the right choice for you.