someone in his camp is smart/devious/slick enough to advise him to test his autocracy by skipping the rules on things that are already obvious before moving on to skip the rules on more dubious and unpalatable endeavors

I would liken it to testing the electric fences in different sectors like the velociraptors from Jurassic Park, starting with the sections that are hidden from cameras by bushes, before knocking down the ones out in the open.