Jared,
Jared, as long as the headsail can fill on its own, the pole isn't necessary, When you fall off a broad reach so deeply that the headsail begins to collapse, you're very near DDW, and throwing the jib over to windward, poled out wing-on-wing, becomes the better sail configuration.Yes, the pole allows steering slightly above a DDW, w/ the headsail poled out to windward, as Pete suggests. This reduces the chances of an accidental gybe, one of the constant dangers of trying to steer DDW or sailing by the lee in order to keep an unpoled headsail filled. The two diagrams in Jared's link show the range of steering within which the pole is effective. It's nice to be able to sail (read maneuver) within a 20° range instead of a 3-4° range without the pole. Buying a whisker pole for my 22' boat was the best $85 I ever spent as far as increased sailing pleasure was concerned. On a small boat it's easy to rig, deploy and stowOh, and if you're just flying a 110° jib, a turning block mounted behing the winch that Pete describes is superflous, though with his drifter he's certainly right.Enjoy!