Evan Schuman's StorefrontBacktalk

There’s also a key sales point behind the scenes here. Years ago, in the early days of in-store kiosk strategy, the popular approach was to use the kiosk to replace floor associates or, to be nicer, make do with far fewer store associates. However, it didn’t take long for store execs to realize that consumers didn’t like being pushed off on a machine, as though associates were saying: “Get away from me, kid, until you’re ready to buy. I have more important things to do.”

But when those same associates started using the kiosks as sales tools—by standing with the customer, handling the kiosk controls and using it for demos, product searches and whatnot—sales took a decidedly northward spike.

By arming floor associates with the devices, it not only frees customers up—and enables those who don’t have smartphones—but it puts the control back into the hands of the sales associates. That’s one way to discourage sales from slipping away to Amazon or JCPenney.com.

Sears is rolling out the Apple devices slowly in the U.S., starting with 449 stores, according to the chain. Although opting to not say when it expects those initial deployments to be in place, the upcoming holiday season certainly suggests it will be completed quickly.

“The rollout is happening now, and we hope to have it completed by the holidays,” Freely said.

At 449 stores, that represents about 13 percent of the roughly 3,500 Sears and Kmart stores in the U.S.

Sears’ announcement also said that the chain would be offering free Wi-Fi at 377 stores.

The idea of pushing Wi-Fi is a solid one. But where many have dropped the ball—and we haven’t seen anything from Sears yet to indicate that it has addressed this—has been on consumer handholding. There are three parts to that. First, making sure any smartphone-possessing customer who walks in the door understands that Sears has a free Wi-Fi network for their unlimited use. Second, making sure the customer knows how to use it. (That second one is going to be needed by an increasingly small population, but they do still exist. Signage and associates need to talk about how to access the store’s Wi-Fi for various smartphones.)

But the third issue is the most critical: convincing customers it’s safe. In consumer-friendly language, mention the security precautions that will protect them from any malicious fellow Wi-Fi shoppers. Without that third one, many shoppers will simply say “thanks, but no thanks” to the free wireless ride. And there goes all of those mobile-friendly new sales.