This is a complex but often practiced technique of increasing the yield from a rough diamond by a diamond cutter. There is a lot of discussion in the trade about painting and digging out, and it can affect the overall light performance significantly if either is significant.

Basically, the technique involves adjusting certain angles of the final faceting of the crown or pavilion, either inward or outward. This makes the facet junctions a little less pronounced, and thus gains a little extra weight from the rough. These angles are important to the flow of light internally however, so it affects Symmetry and overall Light Performance.

Here is a great article by GIA about the subject ::

Painting and Digging Out : Variations on Standard Brillianteering of Round Brilliant Diamonds

Here is an image that describes the technique in the simplest terms ::

Screen Shot 2013-12-06 at 4.47.03 PM

Here is the GIA explanation for the image ::
“Comparison of single-cut face-up diamond outline (top) with painted crown (middle) and dug-out crown (bottom) variations. Violet lines represent low angle facet edges. Painted crowns lead to upper halves that are barely discernible from the bezel facets (middle), causing the fully brillianteered diamond to resemble a single cut. Digging out (bottom) causes the upper halves to be barely discernible from each other.”