Directly behind the boat and with a short tether is best. I use two on my boat and if you have them on the side of the boat, it really messes up your control. Keep an eye on it (or them if you use two) so you know where it is in relation to your gear. Making lazy S turns also helps to keep the speed down. Nothing much more to say. You can allways experiment with the length but it's really pretty simple once you start.
Ayuh,... I prefer 'em tied off to the forward cleats, so they run along side of the boat...
It kkeps 'em outa the way when fightin' a fish at the stern...
And,...
Get the Biggest you can get...
I've seen folks just tie an old car tire off the side/back of boat with an appropriate length of rope. Maybe one each on the forward cleats like Bond-O said...two tires=lots of drag!....
When trolling I tie my drift sock off with 2 ropes on the cleats that are about 2 feet away(18 foot boat) from the bow.One rope on each side.That way ,the sock is under the boat and it is never in the way of a fish that is to be brought in.It also stabilizes the boat and the boat never gets pulled off to one side.
Depending on the size of the boat (my brother's is 16') 1 or 2 "homer" buckets ($5 bucks each) from home depot tied off over the side work really well too!