Regarding the questiong about "revenue" flights - the companion pass could be earned by points, but also by number of flights taken - only flights that were paid for would count towards the total, if your boss takes any flights that are paid for with points then these won't count as revenue flights. ...But it sounds like you were pursuing the points method. Hopefully he made it. If he turns out to be close again next year, consider a strategic upgrade to business select to bump up to 12x points if it is that close.
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