Select the correct sized drill bit according to the size of pipe that you are inserting; the bit needs to be slightly larger than the pipe.
Wet the area of the pot that you will be drilling.
Position yourself so that you are able to drill comfortably into the clay at the same angle that you will insert the pipe. Have your helper steady the pot with one hand -- she will need the other hand to apply water to the terra cotta surface as you drill.
Drill into the clay without force. Pushing too firmly will crack the terra cotta; allow the drill bit to do the work as it spins.
Drizzle or spray just enough water onto the clay surface to keep it damp until the bit is completely through. Guide the spinning drill bit back out of the hole in the same direction that it went in.
Repeat the drilling process on the other side if you need the pipe to pass completely through the flowerpot.
Remove the dust from around the drilled holes with a damp rag.
Insert your pipe through the hole/s. If a hole is not large enough or needs further angling, gently rasp in the ideal direction using a file.
Apply sealant or caulking where the pipe and terra cotta meet if you need to make your project waterproof or securely fix the pipe in place. Smooth the caulking around the hole and pipe with your finger. Wipe the caulking off your hands before it dries. Allow the sealer to dry on the pot for the suggested time on the tube’s label.