You'll know right away when riding if the steering head nut is loose. When you go over bumps you'll feel and extra jolt in the handlebars.
Mine keeps coming loose, well until I got it torqued down to proper specs. I got it torqued down a couple of weekends ago (thanks 14ter) before one of our weekend rides and it's been good to go since. Just take that rubber cover off the nut right under the handlebar in the center, mine was hand tight.
I used a sharpie to mark the nut/bolt once it was tight to make it easy to see if it starts to come loose. Now I can just pull off the rubber cover, if my line is 'broken' I know the nut is coming loose. I intend to check it once every week or 2 for a bit to ensure it does not come loose. Torque spec is 94 ft lbs, I had to use an extension on my socket so I set it to 100 ft lbs due to loosing torque due to twist in the extension.