This all sounds VERY suspicious...

"There was a mismatch of expectations in the presentation of a new product..."

"The CEO of a 3,000+ person company had to approve a $1,500-2,000 trip for a sale worth tens of millions of dollars in revenue."

The way you are presenting this Steve, sounds very slanted. It sounds to me like your friend the sales person either "oversold" or flat out made promises that are false. That's a very good term; "mismatch of expectations", (and to come up with it you might have a great future in Washington DC where there have been a few recent mismatches of expectations) - but if, as you say this is a sale worth tens of millions of dollars in revenue, how did your friend manage to create a "mismatch of expectations"? With that kind of money at stake, surely a bit more caution and clarity should be in order.

None the less, suppose this 3,000+ person company is sitting on the verge of bankruptcy? Would you then argue the CEO should not be concerning himself with this seemingly minor expense? If I were the CEO, I would not only be a little concerned about the expense but WHY the expense is required AT ALL!!! Sounds like it is required because your friend basically "screwed up".

Sure, trust your people to do their jobs - but if you have a person who develops a "mismatch of expectations" where tens of millions of dollars are at stake, you'd better put this guy under the microscope - because its not the ten minutes the CEO will spend to unravel what happened there that matters - its a sales guy who clearly is not doing his job as he should. And whether its a company with 3, 300 or 3,000 - you'd better get that fixed soon.

In other words, yeah, a $2,000 expense is minor - but a mismatch of expectations with a huge valuable client IS A MAJOR CRISIS that indeed requires some CEO attention!