Your instructor wants you to "stop taking safe photographs" and wants your images to "talk to him in some way."
My instructor said this to me once. Somewhat paraphrasing, he says I seem to be taking photographs of things that I know will produce a good photograph. He didn't think there was any ME in the photograph. He also said don't take this advise literally.
I think mine and yours are saying the same thing.... Mine were "good photographs" but it really didn't say anything. For example, they were nice photograph of some landscapes.... but I had no passion in landscaping or geography, so to me, it was just a nice scene.
I went into several branches of photography and I think I found my home in portraiture - especially family portraiture. There's a lot of ME in it although I am not literally in it. I convey what I see, what I want to see, what I want them to see themselves did/do, I have their emotions through my emotions, etc, etc, etc. It's my interpretation of what I thought that family represented. In other words, my photograph showed my unique view of the family.
Successful or not, that's not for me to decide. I think some of them were.
Do your photograph do that? Does it show your unique view of the object with your experience, view point, ideas, etc, etc, etc? Or just a nice photograph of something?
Your professor obviously wants you to think and think on your own. Come up with your own interpretation of what he said and show it in your works.