Praise where praise is overdue
I recently attended a training day where this issue was raised. The problem is this; you are praising your insecure pupil in the same way you praise others.
If you say "well done" to a confident pupil, he or she just feels more confident. But if you say the same thing to someone with low self-esteem, it has no impact at all. It can't be me, he or she thinks; I'm a failure and I know it because I have evidence of my failure.
You simply have to be more precise with those with low self-esteem and you have to accept that you can't turn them around with one well-meaning phrase. It is important that you direct their attention to precisely what part of their work has warranted your praise.
Use previous work to measure the improvement and by doing so, you make the idea of improvement unequivocal. Be sure to record this improvement, too, because on another day the same pupil may easily believe it didn't happen.
But that is just the beginning. Remember that trying to come back from failure is like walking through estuary mud.
Dilemmas should be emailed to Donald Short at firstname.lastname@example.org