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It should always be safe, legal, reliable, in that order. If the procedure is contrary to safety, then it needs to be changed. ASAP is the means. If people are doing something different to keep the system working, but it is not compromising safety, then, again, a change needs to be made to have the system match what is occurring. SMS is the tool to find and fix those kinds of issues.
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Procedures, and the FARs aren't always what's safest either. I do what is the safest procedure that I can come up with in the airplane at that time. I'm not going to do something that's unsafe even though its procedure. For example, procedure has us reducing power from max cont. to cruise-climb at 500'AGL, well, sometimes that's just not going to work because there's terrain in front of us that needs to be cleared. Same with retraction of the flaps, which is procedurally required at 200' according to the checklist, that doesn't work all the time either, especially if we're in the turn climbing out of a valley (like PAGY) sometimes we need to actually add flaps to keep from stalling. Do what's safe first, don't follow bad procedures or contextually inappropriate procedures into a coffin. I think that's what Boris is getting at here.
As for when legal issues that could be unsafe, sometimes it comes down to which law do you follow in an abnormal situation (such as getting caught out in bad weather)? Do you bust your cloud clearance rules, but maintain gliding distance to shore? Or do you go off shore to stay "legal" on one end but you'll have to put it in the drink if you lose a motor?
SAFE, should be the overriding premise, or as one fellow JC'er put it to me:
ASS, LICENSE, JOB, and in that order.
As for the other "what would you do if..." its all irrelevant, each type of operation handles these situations differently and the contextual lens through which we are viewing this discussion is so vastly different from one perspective to the other that this discussion in and of itself is based on flawed logic. When you're taxiing a 185 on floats on the Mississippi you may not have time to use the checklist before takeoff, lest you run aground, hit a boat, or hit a large piece of floating debris, or otherwise damage yourself or others, you have to have everything memorized. Similarly, the guy coming from the single pilot world will say, "well hell, the guy probably knows what he is doing because hey, I did a bunch of those things and knew what I was doing." Indeed the single pilot freight dawg might not even find it possible to use inflight checklists in the severe weather that they fly through. That doesn't make it wrong, or dangerous, its just different.
The problem is when a pilot transitions from one type of operation to the other. Its bad juju for the airline captain who transitions to a single pilot corporate world to think, "HEY, THIS IS HOW WE DO IT AT <BRAND X>, THUS ALL OTHER MODES OF OPERATION ARE DANGEROUS," despite the fact that the operation targeted by such slander probably has thousands of accident free hours that underscore the contextual relevancy of their procedures and levels of crew autonomy. Similarly, the freight dawg / bushrat / etc. transitioning to a more controlled and structured world should bear in mind that doing 200kts to the final approach fix, configuring all the way down the approach to the marker, then breaking out at mins is not how its done everywhere, nor how it should be done in slicker airplanes with more people on board.
Let us also bear in mind the fact that this whole charade of a career we call aviation is built on the hypocritical notion that for-profit companies are going to willingly comply with safety legislation that limits their already slim margins. Many many companies push their pilots and the limits. To suggest that many of us have grown up in such an environment and consider it normal, is not a stretch. So what one considers "normal," and "realistic," may not in anyway be congruent with the outlook and methodology of another.