As it relates to hockey, they’ve seen more minutes of more games than I’ll ever watch in my lifetime, and see things in players that I’d never know to look for. They can compartmentalize all of the information that they’ve accumulated about the game over their life-times and draw comparisons to current and future players in an instant.
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They’re also true professionals of their craft. They see the game differently than you or I. Some of that is dictated by their respective roles with the team, as a coach and general manager, but a lot of it is probably just from being around hockey for their whole lives and knowing what works and what doesn’t.