If you have a video cord you need to pass through the hole, there are a couple of things to keep in mind. First and foremost, you will want to consider the cord size and hole size. A typical HDMI cord, say, has a thick connector, so the hole has to be big enough to fit the head of that through. If it is too small, you will have to make it larger, using a drill bit of the same or slightly larger dimension of the connector.

Determine What's Behind the Surface Before drilling. If the hole will be punched through a wall, check to make sure there aren’t any wires, pipes or anything else that it might punch through on the other side. If it involves furniture or a desk, things tend to be more straightforward, but the fundamental principle is the same. Once the hole is prepared, you’ll be able to feed the cord through. And yes, try feeding the connector end through first, it's generally the largest part so might help when pulling the cable through behind it. Avoid forcing it, as that could damage the connection inside the cable due to the coiling of the cord. Pull the cord through and make sure that it is long enough to reach the device you are connecting it to. Leave a little excess so the cable is not stretched when tightened.