Did Buddha ever say how to overcome shyness? In AN 9.5, the Buddha said that whoever is endowed with the four powers has left behind the fear of embarrassment in assemblies. Is this the same as shyness? If not then did the Buddha ever say how to overcome shyness?


  There are, monks, four powers. The power of wisdom, the power of energy, the power of an unblemished life and the power of benevolence....Now, monks, a noble disciple endowed with these four powers has left behind five fears: the fear for his livelihood, the fear of disrepute, the fear of embarrassment in assemblies, the fear of death and the fear of an unhappy future destiny.
  
  AN 9.5
I would say yes, these powers include the overcoming of shyness. You are no longer meeting other people but just yourself in other guises. Also, your mind is not weaving fantasies about what people are thinking about you. Also, you have nothing to hide, no sense of superiority or inferiority and if you are sufficiently skilled no sense of personal involvement in the situation.   

Maybe a little shyness is a good thing but a Buddhist has excellent defenses against being crippled by it. A good Buddhist knows he or she is an idiot and is not surprised when others think so. I'll let you know later whether this is also true for arhats and buddhas.