I always felt that the problem with mats isn't with the grossly mishit shots that would make your 6i shorter than your PW, which would be an obvious indication of something wrong.
Rather, I feel it is in the slightly mishit shot where you just hit it fat. On grass, it would still be a fat shot, but on the mat, the club head glides along the ground (kind of like a slap shot in hockey) and then makes decent contact with the ball. The feel is definitely off, but if you judge your swing purely by the flight, you are led to believe that you hit a pretty decent shot, albeit slightly off the sweet spot. Then you go to the course and you're hitting it fat and thin all over.
I don't really have many options for grass ranges where I live, so I have learned to distinguish the feeling of crisp contact off a mat. It's definitely something you have to be consciously aware of, though. The important thing is to get the swing to bottom out in the same spot consistently.
My advice, since the OP has already scheduled lessons for his son, is to work with the pro and go from there. In the meantime, try to keep things light and fun. After all, isn't that why we play this game?