Many moons ago I was involved with an airline as a low level life form usually referred to as bean counter. I had the privilege of having worked alongside a COO who could actually think in 256 shades of grey as opposed to the usual #000000 and #FFFFFF. In this outfit flight crews were actively encouraged to use sound judgement within the bounds of regulations, and also to consider the financial impact of their action when making decisions.
There were two scenarios (among some others), where crews were explicitly instructed to ignore any financial consequences - when deciding to go-around or when considering to de-ice. In both cases SOP called for "if in doubt, do it - no questions will be asked later".
Over the years the most serious incident we had was someone getting the nosewheel muddy after the 'caution, slippery when wet' sign was removed from the piano keys.