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Questions for player evaluation

Following the usual advice I am having a guy "take a look at" my 8th grader. Son is a two-way player but pitching is his main thing and that's what the evaluation will be about. The person we found seems to know the local baseball scene, played at a high level back in the day, and has stayed in baseball through travel ball coaching.

What sort of questions should we ask? I have asked for recommendations for local trainers and travel organizations. Anything else important at this stage?

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