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Last year, I bought my 87-year-old grandfather an iPad 2 to replace the who-knows-what PC that was frustrating him constantly. He only used the PC for email and playing music, so it was a no-brainer.

Since my grandparents live in Arizona and I usually only see them a few times each year, I can hardly ever provide in-person help. And telephone support is difficult: they’re not tech experts, they have trouble recognizing and describing interface elements, and they feel bad asking me for help because they know it’ll take a while. So usually, they just tolerate whatever problems are plaguing their technology and they don’t even tell me when something’s broken until months later.¹

Here’s what my grandfather can do on the iPad:

• Check and send email
• Play music, mostly from the 1940s, with Pandora and the built-in Music app
• Accept (but not place) FaceTime calls
• Use Maps with Street View (well, not anymore) to see what has become of the Brooklyn buildings and houses he lived in 60 years ago (surprisingly, most of them are still there)

And here’s what my grandmother can do on it:

• Quit whatever my grandfather was doing, launch whatever version of Solitaire I installed on it last year, and play exceptionally well for hours

Here are some things they can’t do on the iPad:

• Sync and back it up regularly to iTunes on their who-knows-what PC
• Plug it into iTunes and update iOS (it shipped with iOS 4)
• Dive into Settings, even with phone guidance, and tell me which iOS version it’s running
• Join new Wi-Fi networks reliably

They’re not stupid — far from it. My grandmother beats us all in card games, figures people out spookily accurately within seconds, and can tell you everything that has happened to every character in every soap opera since the beginning of time. My grandfather is still a licensed and practicing civil engineer in two states, a high-school math and physics tutor and substitute teacher, and a recently retired competitive swimmer with quite a few gold medals.

They just didn’t have computers for the first 80 years of their lives, and they’d rather not spend their current years dicking around with Windows malware or Apple IDs.

The other day, my grandfather asked me if he could get rid of the who-knows-what PC for good, but he wanted to make sure that he could transfer his stuff to a new iPad in the future if this one ever broke. (Good question.) I told him to bring it to the nearby Apple Store and have them set up “ICLOUD BACKUP” for him. (He wrote that down.)

I figured that a “Genius” would quickly figure out whether it still had iOS 4, and if so, would just update it to iOS 5 or 6 and then set up iCloud backup.

But instead of doing what I assumed would be a non-destructive update, the Genius did a restore. And, apparently, didn’t explain what that was going to mean. My grandfather left me this voicemail:

It’s easy for most of us around these parts to forget how badly technology still works for so many people. This is supposed to be the best we have today: an iPad, a routine OS update, an Apple Store, an automatic backup feature.

But even the iPad, while easy to use for routine tasks, still shows its computer heritage in clunky, ugly, techie ways like software updates and restores. And while Apple Stores have a reputation for great service, there are enough counterexamples happening every day that I’m not sure how much longer that reputation will last.

This seemingly simple procedure failed the customer miserably, yet I doubt the Genius thinks it was anything but a success. Here you go, all restored and set to back up your data! (After you put some data back on here!)

The Genius probably thought, Of course he syncs it with his computer regularly.

Or There doesn’t appear to be much here. It shouldn’t take him long to set it back up again.

It wouldn’t be the first time a technology expert lacked empathy for a customer, or made bad assumptions about what would be fast and easy for the customer to do on his own — especially when deciding to perform an easy, predictable, cure-all “restore”.²

And the iPad wasn’t the first personal computer, nor will it be the last, that we all proclaimed to be finally easy enough for everyone to use. Sure, it’s easy to use when everything’s working and time stands still, but that’s about as useful as when a developer says, “It worked on my machine.”

We, all of us in technology, can do better than this. And we have a long way to go.