How to provide Mac help from far away

It happens to me a lot. It happened just a couple weeks ago when Dad bought a new iMac. And it happened just a couple days ago when Uncle Mort found that Firefox was bizarrely loading with a bunch of extra tabs that he didn’t want and couldn’t get rid of. And it happened when my sister-in-law Sam wanted to get access to music she’d purchased with an older Mac.

My friends and family turn to me for tech support, and I’m happy enough to offer it. But I can’t always provide that help in person. I often need to do it remotely, since not everyone who seeks my Mac guidance lives near me.

Here’s how I do it.

Calm, cool, and collect information

When my father first needed help with his new iMac, he tried to FaceTime me. I was on a conference call for work at the time, so I ignored the FaceTime request, along with the subsequent calls to my home and cell phone. But I knew he was trying to reach me.

I was finally able to call back about 40 minutes later. By then, I think his frustration had raised the already-high ambient temperature in the Tucson area by a few degrees. Turned out he hadn’t even unboxed his new iMac yet; he was too worried about how he was going to transfer his existing POP3 email from his old iMac to his new one. The method he’d tried, under Mom’s careful guidance, involved dragging mammoth mailboxes into a separate IMAP Gmail account for transport—a process that, as it turned out, had been fraught with issues: messages disappearing, inconsistent mailbox counts, and so on.

My first role, then, as the remote tech support representative assigned to the case, was to provide calm reassurance. In this case, it was easy: I asked a few questions. “Did you ever get started with CrashPlan?” I asked. “No,” Dad replied, “because I found a cheap USB drive to use with Time Machine.” Perfect. I walked Dad through checking on how recent his Time Machine backup was (from the Time Machine menu), confirmed it was good and healthy, and dropped a calm bomb: “No matter what, no messages are lost. We can get them all back.” That immediately cooled things down.

Out of sight

Next, I did what any self-respecting, self-professed tech expert would do: I Googled for “how to move Mail mailboxes from one Mac to another.” The first result pointed to a Macworld article on exactly that topic by Chris Breen.

One of Chris’s steps involves navigating into Mountain Lion’s hidden ~/Library folder and finding the Mail folder therein to copy. Now, a certain class of grizzled Mac user can come up with at least three ways to get to that folder and copy it in an instant. My dad, a retired orthopedic surgeon, is great at reading x-rays and fixing bones, and he does just fine with his Mac, iPhone, and iPad most of the time—but he’s not a member of that grizzled class.

As I tried to get Dad to hold down the Option key while accessing the Finder’s Go menu, to make Library appear therein, what he reported seeing on his screen didn’t match my expectations. We tried to get screen-sharing going with Messages, but that proved difficult for other reasons, and I hate going down the rabbit-hole of solving problems a degree or more removed from the initial issue.

Eventually, though, I realized that I could be even more literal than I’d been. “Click on the Finder icon—the leftmost one in your Dock—just once. And now, you should see Finder in the menu bar, just to the right of the Apple menu. Now, hold down the Option key with your left hand and use your right to click on the Go menu once more. Select Library there.”

Although the instructions were overly detailed that time, it eliminated whatever confusion we’d encountered before. Then I wanted Dad to find the Mail folder in his Library folder. My instinct is to use keyboard navigation in such circumstances—typing out the first letters of Mail to find the folder. But Dad, who’s unaccustomed to that approach, instead typed Mail in the search box at the upper right of the Finder window. That search box (stupidly) doesn’t default to searching just the current folder, so Dad got nowhere fast. I had him clear out the search, resort the window alphabetically, and scroll through it until he found Mail.

The important takeaway is that when guiding folks with computer problems, guiding them to do things the best or most efficient way—i.e., your way—isn’t always the best idea. I certainly advocate for sharing your power-user tips and tricks with friends and family, but maybe not over the phone.

Remote control

When Uncle Mort needed help, though, his problem was trickier to solve without being able to see it in person. The most talented Mac users you know sometimes solve problem not because they know precisely what they’re doing, but because they’re comfortable poking around until they figure out what’s amiss.

Uncle Mort’s complaint was that Firefox was loading up a bunch of tabs every time he opened it, and they’d come back if he closed them. And he told me that his homepage appeared to be set properly in Preferences. I was stumped.

We tried simple solutions: restarting the browser, restarting the Mac, prayer. None of those worked. I talked Mort through trying to see whether he had any extra toolbars installed. It seemed he didn’t.

At this point, Mort’s unwanted, endlessly-resurrecting tabs seemed like just the sort of problem I could solve in a few minutes, were I right in front of the afflicted Mac. I wanted to poke around his system, but the miles between us made that a challenge.

As I’d asked of my parents, I encouraged Mort to fire up Messages so that we could use that app’s screen-sharing feature. No dice; I was once again stymied by AIM issues—namely, that he couldn’t seem to get logged into his account.

But this time, I was prepared. After the challenges of fixing my dad’s problem, I’d done further research. Turns out numerous services exist that make it possible for you to control someone else’s computer over the Internet. The one I had Mort use was Fog Creek Copilot, which is free on weekends and $5 for a day pass. You follow the instructions on the website, both helper and helpee download and install a tiny helper app, and seconds later, you can control the other user’s screen.

Armed with that power, I found that somehow his homepage had indeed been changed in Preferences, though it was hard to tell since the text field didn’t show that after his desired homepage. In that field were numerous other URLs, all separated by semicolons, so Firefox was dutifully opening them all each time Uncle Mort opened a new browser window.

I deleted the extraneous URLs, and Mort’s Firefox was back to normal.

Know your audience

Sam’s of a different generation from my parents and Uncle Mort. (The 40-to-50 year age gap helps.) When Sam needed help with iTunes, she didn’t call me. She reached out via iMessage. And her question showed a clear grasp of what she was trying to accomplish:

How do I authorize my computer to make iTunes purchases and see what I’ve purchased from other devices?

Sam recently got a new Mac. She’d had it shipped to my house, where I set it up for her to pick up when she visited a couple weeks later. But now she was back at home in Manhattan, realizing that the tracks she’d purchased in iTunes over the years weren’t on her Mac.

I received Sam’s messages on my iPhone, and I wasn’t near my Mac. I knew the basics of the answer, but I didn’t know the exact location of the menu options she’d need.

Whenever you’re helping folks remotely, it’s important to assess their levels of expertise. Had it been my dad with Sam’s issue, I might’ve told him I’d walk him through the steps when I was back at my Mac. But since I know Sam’s a little more comfortable computing while confused, I decided to try to help her as best I could, despite my own uncertainty about the exact steps she needed to take.

So, I replied via iMessage:

Go to the iTunes Help menu and type in “authorize,” and it’ll show you the option.

There was a pause, and then Sam wrote back: “Got it.”

Two lessons from this interaction with Sam stick out at me: The first is that just-mentioned notion of targeting your help to the user’s level of expertise. And the second is taking the opportunity to provide bits of knowledge that can help your friends and family later: Sam knew what I was talking about with the Help menu, because I’d previously shown her how typing into that menu’s search box can find options elsewhere in an application’s menus. Sowing those seeds of knowledge can pay off later—as it did with Sam with her iTunes problem.

A little help for my friends

Look, it’s rarely a thrill to get that “please help me with my technical issue” phone call. Generally speaking, we’re not sitting around, waiting for someone to call us seeking help with their computer problems. Still, those calls are a testament to our friends and family members having faith in our abilities to help.

Once you’re involved, your goal is—fairly!—getting the issue resolved as efficiently as possible, so that you and the caller can both get on with your lives. Know your audience, be a calming force, and make sure you have a method for taking over the remote screen when all else fails. Whether you believe in karma, “do unto others,” or just simply the notion that what goes around comes around, it’s awfully nice of you to help the computer sufferers who rely on you with as little pain as possible for everyone involved.