Here's how to drill a hole when you need to see both sides of your work. Drill on the front side of the board until the tip of the drill bit pierces the back. If you go all the way through, the job will look like this. Now turn your work over to the back, set the drill bit in the pierced hole, and finish drilling from this side. You'll end up with a smooth cut on both sides.
For more on woodworking, consider:
Drill Bits for Different Jobs
10 Ways to Use Your Cordless Drill/Driver
How To: Drill Straight 90º Holes (Without a Drill Press)