Thanks for all the great responses. Aviation has come along way in past years, and I believe Corpporate Attitude has improved immensly which results in measurable safety.
Let me share how I handle these types of situations. First off I have NEVER cancelled a trip due to weather or for a mechanical reason. I can hear the moans and groans right now, allow me to explain. It is not for me to cancell a trip, what I do when faced with weather or maintenance issues is I explain the reason for delaying a trip, I offer to fly the trip at the first safe opportunity ... it may be an hour from now when the front blows over or it could be tommorro or the next day, bottom line is I give the customer (ie:the BOSS) all the options. If these options don't suit him then HE may cancell the trip. If it's a mechanical problem, I again try to figure out the best option for the customer, does he want to wait for the repairs, reschedule the trip or go commerciall or should I arrange for a charter. I have NEVER caught flak for a decision about delaying a flight, and I have told 3 star Generals we needed to wait.
As far as crew resource management issues go, I handle ALL flight issues as CREW issues, not passenger. When faced with a issue I pull my crew member aside and WE discuss all our options, my copilot may see something I'm missing. Once we decide on an acceptable level of risk, I brief the passengers on thier options. One time when this didn't happen, my copilot told the passengers that it was not safe to fly and if he were making the decision we would not go. My blood boiled because he just abricated MY authority. I politely pulled him into another room were I gave him HOLY H**L. The problem was the WX at destination was crappy, but what he didn't know, because he was too busy trying to sound big, was that the WX 25 miles north was VFR and I had already arranged ground transportation for the passengers should we elected to land short of our destination. Now I was faced with explaining to the passengers that it was safe to fly and what options I had worked out should we decide to land short. The way the flight went is we were able to safely fly all the way to the originall destination, the weather cleared out untill we got there. My point here is don't be quick to tell anyone that you are the PIC and that your word is finall. It is not a good way to endear your self to the BOSS, he knows your the PIC, so give him something he doesn't know ... OPTIONS. If you run into someone with the attitude that pushes you into flying when you know you shouldn't, and your not at home base, RUN to the nearest car rental place and get you a ride home before he cancells your company credit card.
