I'm not Gary, but have owned 3 Kenmore water softeners and know a little something about them.
I don't remember the actual brand of softener that Sears sells under the Kenmore label, but GE and a few others use the same one. A VERY common problem, in fact a universal problem in my opinion, is that the "rotor disc" in these units fails after about 2-3 years, and leads to inadequate brine suction. This means that you will have excess water in the brine well after a regeneration, and you'll have at least partially hard water since the brine isn't getting into the resin.
Another common problem is that the rubber venturi GASKET needs replacement if it shows any indentations at all -- it will NOT draw brine correctly unless it's completely flat.
I highly recommend you go to www.kenmorewater.com and click on the troubleshooting animation -- it walks you right through the steps to take to diagnose your problem.
The one thing that site won't help with is actually opening up the valve body and replacing the rotor disc. Your owner's manual DOES have info on this, however. It's a 15-20 minute job and not hard.