My DD's pitching instructor had her pitch a few before he told her anything in her first ever class (about 2 years ago), then he showed her both styles, had her pitch a few each way, watched her, asked her what felt comfortable, etc.
She ended up pitching L and D, btw. One of the key elements on L and D is timing. He really has her concentrate on where her pitching hand is in the windmill when her stride foot lands, for example.
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