But back at the coal face -
Rail yards were a very important and expensive part of a ~1906 railroad's infrastructure - both to build, and to operate. And the efficiency differences between a well-designed and poorly-designed yard were huge. A prospective RR manager who can't quickly map out a good rail yard is someone who simply does not understand the at-scale operation of a railroad.
Similarly, waybills were the core document for moving individual customer's loads around on an RR. If (fake name) EconoAir's manager at your local airport did not understand Flight Plans well enough to quickly draw one up - would you want to own EconoAir's stock, or fly on their airplanes?