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We recently toured a Montessori school for LO who will be 3 in the fall. This will be her first preschool after a year at home with me, so we didn't ask about anything related to a preschool transition. I might google "daycare transition questions" or "preschool transition questions" and similar phrases to come up with some things to ask! Or I might post another thread with a different title along those lines. I know several people here have changed daycares or preschools and they could help from that point of view.

As far as Montessori goes, we asked some pretty basic questions: How do they track progress regarding skills/learning? How do they guide the works the kids are doing? How do they handle conflicts or behavior issues? I know we had a lot more questions but those are the ones that immediately come to mind. In our case they know Montessori is "different" so they gave us a lot of information about their approach up front.