It sounds like there is a conflict regarding what/how to communicate with the children.
I don't think it's fair (to the child or the teacher) to tell a child they don't have to follow school rules, but still put them in that environment. Too much cognitive dissonance--and you can be sure the child will be confused and respond inappropriately (or, really, appropriately but not in a way that will help).
OTOH, I don't think it's fair not to communicate with the child at all.
Sounds to me like everyone needs to take a step back from their own perspectives and try to understand what will be most helpful to the child. It's really difficult when you feel you were actively damaged by your educational experience (each in your own way). It's often the case the best answer lies in the grey areas.
For instance, "I know it's difficult to see the importance of the morning work (validation), but when you are in school, there is value in learning to do things that are challenging for you." (In this sense the challenge is the self-discipline).
Hope that helps a little
