Good interview with Amanda Cox, who made that transition, at Simply Statistics. I love the idea of “poor man’s interactivity” (rapid paging-down in a PDF).
I’m a big believer in learning by example. If you annotate three points in a scatterplot, I’m probably good, even if I’m not super comfortable reading scatterplots. I also think the words in a graphic should highlight the relevant pattern, or an expert’s interpretation, and not merely say “Here is some data.” The annotation layer is critical, even in a newspaper (where the data is not usually super complicated).
More interviews with and presentations from Cox: here, here, here, here, and here.