Agree with WSUshox and No RYR for me,
Normally the boss is a person who rarely gets a plain NO for an answer, and he really needs alternatives not only to plan a new course of action for something not executable as he thought, but also he can be put in a really uncomfortable position if he do not get options, not good for the PIC. If he trust you, he will follow along your options.
jr of dallas: It could be a good idea to write a "little book of common sense manual for corporate operations", it will help a lot of people. But in my experience some pilots (the least) will never adapt to this environment where
PR and flying abilities intermix so much. I've seen many very good pilots fail to work properly outside the aircraft environment, being released because they cant produce a good atmosphere to work, or simply are two steps back behind the boss needs... You really need to adapt to those conditions which are particular to every CEO. But this also applies to many other lines of work that might be useful to other people too.
Tevor, did i sounded like your CP? Well, when I was writing the post I thought it sounded like my prior CP too! Hahaha! Seems tribal knowledge orally transmitted knows no boundaries!