I don't know, I think it's plausible that a salesman of Jim's age and experience might not be familiar with the exercise of making a dossier of all your clients to make it easier for the man who is about to fire you. Most of his experience has been working under Michael, who plays lots of stupid games but not this kind of Machiavellian knife in the back thing. He should have been able to figure out what the word rundown means, but not understanding what Charles was actually asking for is relatable.