The former are following a script with most everything they do, while the latter have enough understanding to think in categories of behavior and to predict or explain things, at least a little, which doesn't make them immune to phishing, but does make them significantly harder targets. The latter sort are less common than one might hope, even among those younger than Martha, though, which becomes clear if you talk to people who work in non-technical offices—bearing in mind that all but the oldest workers are now mostly Gen X and Millennials, with only a few raised-on-phones Gen Z so far.
Overall, I'd say all signs point to every general-purpose desktop operating system being a usability and security disaster for at least half the population of non-oldsters.
You can't get rid of the Marthas because the Marthas have been here 30 years and hangs out with everyone from the company on weekends, and probably knows more about the business than anyone even if you wanted to get rid of her.