Almost every player has one side that is better than the other. Usually, a player's forehand is stronger but as the level of play gets higher, many players prefer their backhand. Once you have determined which side is better, try attacking the weaker side with your first shot—either the serve or return of serve.
Immediate pressure on their weaker side could result in a lot of early unforced errors. This should work pretty well until the player realizes that most of your first shots are going to their weakness. Once the good players are on to your strategy, you may have to play some first balls to their stronger side to open up the shot to their weaker side.
Another good way to attack an opponent's weakness is to hit your forcing or winning shot to that side. Even if the opponent is in position for it, it is less likely that they will hit a winner or reply with a shot that will give them control of the point. A player's weaker shot tends to break down more under pressure so even if they are successful and hit some decent shots off of their weaker wing, be persistent.
The more balls that are hit to their weakness, the more pressure there will be on that particular shot. Don't forget to keep the opponent honest by serving or returning serve to their strength once in a while.
Steve Annacone, USPTA Elite Pro, is the Director of Annacone Tennis (http://www.annaconetennis.com) MyHamptonsPro (http://www. myhamptonspro.com) and Baron’s Cove Resort In Sag Harbor, NY, as well as Volunteer Assistant Coach for the University of Arizona Women’s team. For details on lessons, clinics, or coaching, contact Steve at email@example.com or call 865-300-7323