It’s always Computing 101 in tech support

Here’s a tip when you work in tech support: Don’t assume anyone knows anything about anything. From assistants just starting out to top executives with years of experience under their belt, there’s no telling who’ll put in a help desk request that’s so basic, it barely qualifies as technical at all.

Still, it’s our duty to help get them back on track. If we happen to hang on to these encounters to get through too-serious days — well, they don’t need to know.

[ Pick up a $50 American Express gift cheque if we publish your story: Send it to offtherecord@infoworld.com. | Get a dose of workplace shenanigans — follow Off the Record on Twitter. | For a quick, smart take on the news you’ll be talking about, subscribe to the InfoWorld TechBrief newsletter. ]

Back to basics: What is a computer?

I was working at the company’s IT help desk and received a call from an assistant who was having computer problems. Her only statement: “The computer won’t turn on.”

I asked for clarification: Was it the computer or the monitor? There was a pause while she thought about it, then answered hesitantly that she was pretty sure it was the computer. She’d pressed the power button a couple of times, but nothing happened.

I went through the routine steps, had her check that the monitor was powered on and all the cables were plugged in. She said yes, but still nothing happened to her computer when she pressed the power button. I even had her verify that the power indicator wasn’t lit. At this point I expected a hardware failure. It was time to see what was happening in person.

When I arrived, I had to hide my surprise when she showed me the “computer” in question. It was a laptop docking station, monitor, keyboard, and mouse — with no laptop in sight.

I then had to explain that the system wouldn’t work without the actual laptop, as the dock was just an accessory that allowed her to use the laptop in tandem with the monitor, keyboard, and mouse. It was not a computer.

Where’s the laptop? I asked. She explained that her manager had it with her at a conference out of town. We were at the manager’s workstation, and she had called asking for a file from a shared network drive to be emailed to her. The assistant had assumed that she needed to be on her manager’s computer to access the file. I explained how the network drives worked and showed her how she could retrieve it and email it from her own computer.

I’m proud to say that I managed all this with a professional demeanor, while internally laughing hysterically.

When in doubt, blame the hardware

Everyone providing internal tech support at one time or another has encountered the executive that absolutely loves, but does not necessarily understand, technology. I’m certain there are literally thousands of such stories. Here are two.

One of my most memorable personal interactions of this type occurred when I was working for an agency that hired a new executive to run one of its divisions. I was assigned to set up this executive with the usual equipment: smartphone, desktop computer, and a laptop with VPN access so that he could connect to our network from home or while on the road at conferences.

The first time I met the executive in person, he spent 20 to 30 minutes telling me all about his rooted Android phone, how he never calls tech support, and how he had been offered the CIO position at his previous company but chose to come work with us because the job was more challenging.

“This’ll be interesting,” I thought — while hoping we wouldn’t have to cross paths again anytime soon.

But the first time he took the laptop home I received an email, sent via his smartphone, informing me that he was unable to connect to the VPN with the laptop. I called him and began to troubleshoot the issue over the phone. He became increasingly agitated about the “defective” laptop he’d been given.

Ignoring him as best I could, I kept troubleshooting. Eventually it became clear that he couldn’t connect because he never joined the laptop to his home network. He assumed that by clicking on the VPN program, the laptop would connect to the Internet all on its own.

When I pointed out the problem, he tried to blame IT for not designing a better VPN program. I again bit my tongue, helped him connect to his own network and access the VPN — and got off the phone as soon as I could.

At least there’s a little satisfaction in witnessing a “pride goeth before a fall” moment, even if the person doesn’t acknowledge it.

Road rules

Another executive who absolutely loved technology insisted on having an iPad rather than a laptop, since she didn’t want to carry a heavy notebook. Enough higher-ups backed her request that the company provided her one in lieu of a laptop, though it wasn’t a standard policy.

The iPad had a data plan, so there were no worries about connecting to the local network. It was also configured with VPN and remote desktop software to allow her to work while on the road. I spent two hours making certain she was familiar with the process to establish the VPN connection and to remotely access her desktop computer, including how the software allowed her to control the system back at the office.

For a while, everything seemed to be going smoothly. Then she went out of state to a national conference.

I received a phone call from her Sunday morning, saying the remote desktop app wasn’t working. I walked her through all the steps to make sure she was doing everything correctly. She appeared to be on the right track, but the connection to the desktop failed every time.

In a flash of inspiration I asked, “Did you by any chance turn off your computer before you left?” She replied, “Of course. I am out of town for two weeks, so there was no need to waste energy.”

I had to explain — again — that the remote computer connection worked only if the computer was turned on. Then because the presentation she was supposed to give the next morning was residing on her computer’s hard drive and needed to be sent via email to the conference organizers by 5 p.m., I drove into work on Sunday to turn on the computer.

She was horrified that she made such a simple mistake and caused me extra work on the weekend. In fact, she bought me lunch to apologize for her error when she got back from the conference.

The apologies are appreciated, the surliness tolerated, and user misunderstandings numerous. That, of course, will never change — no matter how much tech evolves.

Send your own IT tale of managing IT, personal bloopers, supporting users, or dealing with bureaucratic nonsense to offtherecord@infoworld.com. If we publish it, we’ll send you a $50 American Express gift cheque.

This story, “It’s always Computing 101 in tech support,” was originally published at InfoWorld.com. Read more crazy-but-true stories in the anonymous Off the Record blog at InfoWorld.com. For the latest business technology news, follow InfoWorld.com on Twitter.