I reckon you ought to have the ability yourself in order to have a realistic chance of judging whether the other person has the skill. In Heortling society that means that about half the people could accurately judge a fight between two 1W fighters but I doubt if they could reliably tell if it was luck or skill that detirmined the outcome between two W2 fighters.
The thing about a group training together is that they generally all have a similar level of skill so they generally can all judge one-anothers skill. A significantly more skilled person in the group *could* fool the others if they chose and this can be a useful story element e.g. a 10W2 fighter throwing a fight against a 5W opponent - anyone in the audience not at his approximate skill level has little chance of spotting what has really happened. We need this level of misdirection to allow all sorts of stories - how else can we have ringers, stings and various other cons?
You could have a "Good judge of others abilities" as an ability - very useful to and yet very rare amongst managers. Then of course some people will have "Exaggerate skill" as an ability or "Make Excuses for Failure" all of which will complicate matters.
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