Any landing on a such a low gravity object object would require some form of anchoring, which you can use to to get the drill started. The Philae lander (was de

Any landing on a such a low gravity object object would require some form of anchoring, which you can use to to get the drill started. The Philae lander (was designed to) use its impact velocity to drive ice screws into the surface, before fireing a harpoon. Presumably such a harpoon could give sufficient leverage to get run a drill. Of course, if you followed the landing, you know that things didn't quiet go as planned, and Philae bounced a few times (and almost escaped the gravity), so this is definitely a difficult problem, but I suspect that once you have a lander that can anchor itself enought to not bounce, you could probably anchor yourself enough to drill.