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Originally Posted by Rose-Roget 
What I want from his education is for him to be developing his skills - from independent choice-making to socializing to academics, or any one of the above. He has a way of getting people to believe that he can't do things for himself - from putting his coat and shoes on to reading.
My concerns are that he doesn't seem to be developing many of the skills I listed (that I can see from my viewpoint). I'm told that he gets off-task during his works and doesn't focus (this is a kid whose teacher last year - different school - told me he became hyper-focused during his works), he needs a lot of guidance to make choices, still doesn't consistently sit on line without disrupting (this has always been an issue for him), has been working on 3-letter moveable alphabet with objects for months at school (he's on "short u" finally) and tells my mom that he's "avoiding the hard words" - when he can read level 2 readers to me at home (with very little assistance).
These are the reasons I chose Montessori. I'm not trying to push him or compare him unduly. He is a very capable child, and he certainly can learn. I just don't want him to grow into a life of underachieving, and until I find a better way or he finds that intrinsic motivation, I think someone needs to keep an expectation commensurate with his abilitiy.
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Montessori writes a lot about what she calls "the spiritual preparation of the teacher," but the advice she gives teachers hold true for parents as well. She says that "the Montessori teacher is always looking for the child who is not there yet... she sees man as he ought to be: the worker who never tires, because what drives him on is a perennial enthusiasm. She sees one who seeks out the greatest efforts because his constant aspiration is to make himself superior to difficulties; he is a person who really tries to help the weak, because in his heart is true charity and he knows what is meant by respect for others, and that respect for a person's efforts is the water that nourishes the roots of his soul. In the possession of these characteristics, she will recognize the true child, who is the father of man."
I know that when you hear that your child is being disruptive at line time, can't choose his own work, or is still working on the Moveable Alphabet, it can be hard, but try to look past it and see the potential that lies within (hopefully, his guide does).
Two other thoughts:
First, based upon your description of your son, it sounds like Montessori is absolutely the right environment for him. It will encourage his independence and initiative, and should not hinder his development by providing unnecessary assistance.
Second, I certainly understand the pressure that parents (and teachers) feel about ensuring children are progressing in "academic" work (reading, writing, artithmetic), and that it can be really easy to be somewhat myopic about judging a school (and even a student) on the basis of these skills. From your description though, it sounds like your son's "challenging work" right now is participating in the work cycle (choosing work independently, completing work independently, putting the lesson back where it goes, and taking initiative and interest in perservering). I know that it can be frusterating to feel like he isn't making the "academic" gains that you want to see, and that he might even appear to be regressing, but I assure you that it is probably not the case. The guide is probably trying to intervene as little as possible until he learns to participate in the work cycle and shows more self-direction. That will happen in time- but only if someone doesn't rush in and provide that direction for him (concentration and perserverence are like muscles they only develop through repeated use, and no one can "make" another person concentrate). It sounds like this is a big change for him, from an environment where he probably didn't have to be very self-directed (someone was alsways making the choices and judgments for him). During the first few months of school, you might see him doing some "easier" works, because the guide is waiting for that moment where he is able to choose something on his own and really concentrate and polarize his attention on it (and, initially, it doesn't matter what the lesson is, so long as he chooses it). Once concentration is established, then will come perserverence.
For children who began in a Montessori classroom, this happens in the first year (generally through use of the practical life activities), so the second year is really a blossoming (they have the character development to really make amazing academic gains); for your son, it's a little backwards. But, it will happen in it's own time and it really is more important that he develop the ability to concentrate deeply and perservere in his tasks, than it is that he move on from the Moveable Alphabet, because those skills and fundamental attitudes toward learning will serve him for the rest of his life. Every time, you find yourself thinking that maybe the guide should just "push him" a little more, or set higher expectations, remind yourself that it is a well documented fact that children perform better, perservere at a task longer, report higher enjoyment of it (and willingness to do more of it), and develop more self-confidence when they choose it for themself. So, if the end goal is to have a child who loves learning, or loves reading, it really behooves you to be patient and let him come to it himself (to entice, not to force).
Of course, that doesn't mean that your son can't be getting new presentations and moving on academically (although it honestly sounds to me like he is doing very well and that the guides are making good decisions about what to present), but I think it is important to follow the child and to remember that his "important" work right now is not acquiring new knowledge so much as it is constructing his character (he is transforming himself through work- the process is more important than the conceptual knowledge).
Finally, remember that children don't generally acquire habits or knowledge by gradual accretion (so it can be hard to "see" progress). You can have children who just don't understand something for days on end (or always forget to put their lesson away) and then one day, like magic, it just clicks and it is a part of them forever.
To me, his comment about "avoiding the hard works" makes me think that he is probably a very sensitive child who might fear really trying something challenging because he is worried about not being successful (and that being successful is so important to him that it has compromised his ability to take risks). If he says that again, it might be worth having a conversation about the fact that what is important is doing one's best. The Montessori environment is great for children who have these worries (often, gifted and advanced children in particular are so used to being the recipient of praise that it really adds to their fear of failure), because it takes such a friendly attitude toward mistakes (the materials are self-correcting so the child can engage and learn from it without being afraid of error or correction, and the guide makes a point of not correcting the child or interfering with their natural learning process).
Don't get frusterated. Parenting and teaching aren't for the faint of heart

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