I had/have the same problem of being shy and unsure of myself when directing people. I've gotten better but I still get those nervous butterflies. I've found photographing people you are comfortable with in the beginning is really helpful, because you aren't as nervous around them. I've also had my subject bring someone they are comfortable with which reduces their tension and thus mine. Eventually I figure I will be mostly past the nerves part, but we'll see! Good luck to you.
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