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If you get stuck with what you're calling a "money guy," in pre-game try appealing to his sense of how the game is best officiated. Use "we need to..." and emphasize that you're a team. Appeal to those noble motives and that love of the game that brought him to officiating in the first place.
It doesn't always work. But I think it's the right place to start.
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Cheers,
mb
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