I have a ds6 who has underachieving/perfectionism tendencies. Thank goodness his teacher has understood this well, but he'll have a new teacher next year (for grades 1-3) and it's tricky to explain in the montessori context, where there's a lot of choice, that he needs to be pushed a bit to stretch himself. Otherwise he'll choose only easy work. In some ways it might be seen as going agains the montessori method of choice.
I can already imagine down the road how difficult it might be to explain that he may need to be challenged more when he's not seeking out the challenge for himself - but not too challenged (not so much that it's too far beyond his abilities). It's a fine line and might be a moving target to boot.
