Some people have a higher tolerance for risk than others. However the real issues appears to be this:
If a captain with a high tolerance for risk is also having a bad day then there’s increased potential for problems.
As far as the office, in my experience they’d rather not know how sausage is made. If short cuts were taken and the voyage successful they don’t want to hear how it was done. Only if thing go wrong, then the shortcuts will be seen as errors.