Not very well. I tried to make several progressively less deep holes for my cribbage board with a 1/8" ball end mill. About 1/5 of them grabbed some of the walnut its made of and threw a small chunk of wood. I think one of the problems is you have to tell Easel how big of a hole you want, and it has to be bigger than the size of the bit (if it were merely the same size, it might work better).
VCarve has actual drilling profiles, probably using "peck drilling" where it sinks into the material a little bit and then backs out to ensure the cut material is removed from the hole. I'd try that, but I wouldn't use Easel to make holes in anything harder to cut than say, MDF.