SnoopyChicken wrote:How much does he know about you? How much do you know about the industry? If it really is cut throat industry a useful tactic could be to try and make out it's you that's the big fish(or at least will be in the very-near future), if you know the industry jargon and could find out 1 or 2 things about it you could use these to back-up your seniority. Then he'll presume you know the stuff you want to find out and is more likely to reveal useful stuff.
This depends on how well he knows you and how well you know the industry
Either way he's going to be used to people trying to get stuff out of him(likely having used tricks to get where he is now) so you're going to have to display confidence and not appear too eager.
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