I wouldn't describe my DD9 as particularly empathetic, but otherwise, your child sounds very familiar.
One good way to get the information you're looking for is something you're already doing: asking questions in a way that doesn't require your DD to make a value judgement, just relate the facts, like "What did you do in school today?", rather than, "How did you like school today?" Over time, your DD will start to express her judgements along with them.
Apart from that, we found two markers that were very helpful in letting us know that there were major problems with DD in regards to school fit, so it might be helpful to look out for similar signs in your own DD:
- Major behavior changes at home. DD began having meltdowns over spilled milk (yes, literally). Any minor setback was blown out of proportion. DD started calling herself stupid. It escalated to her exploding as soon as she got off the school bus, and hitting her head against the wall.
- Hearing the teachers describe a child we did not recognize as our own. DD was described as compliant and polite (which we recognized), and also shy, quiet, and friendless (which was an alien child). It is true that DD is standoffish in first encounters, but sometime within the first few months she should have warmed up to someone, at which point she reveals her loud and goofy side.
