Working in tech support is a bit like teaching preschool: You’re an educator who provides reassurance in troubling times. You share knowledge and help others overcome their obstacles. And some days, it feels like all you hear is screaming, crying, and incoherent babble.
Tech support is no cakewalk — there’s no question about that — but boy, does it lead to entertaining anecdotes. After all, if the IT pro is the preschool teacher, the customers are the children. And kids, as we all know, are always saying the darnedest things.
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We’ve trotted through the trenches of tech support to dig up truly memorable tales of trouble and triumph. Some of the names and places have been omitted to protect the guilty, but the stories themselves are all real. Honestly, we couldn’t make this stuff up if we tried.
Stupid tech support trick No. 1: The pronoun problem
In tech support, even the most basic assumptions can backfire. Tim Crotwell, a network admin at a Mississippi school district, learned that firsthand — and he’s still laughing about his lesson years later.
Crotwell was working off-site one day when an office manager — we’ll call her Ms. Schmidt — phoned him up with an urgent issue. Ms. Schmidt was trying to print some documents, she told him, and her printer wasn’t responding.
The fix was simple enough: Crotwell just needed to talk her through clearing the Windows print queue and restarting the print job. Tech Support 101, right?
“I told her to go to My Computer and open the Printers folder,” Crotwell explains.
That’s when the case took an unusual turn. Ms. Schmidt told Crotwell to hold on and stayed away for a solid few minutes. When she finally came back on the line, she told Crotwell she had followed his instructions — but saw no sign of her printer in the folder.
“I said, ‘It should be there, unless you accidentally deleted it.’ I walked her through refreshing the list and arranging the printers by name, but she still couldn’t find it,” Crotwell says.
Then, the schmidt really hit the fan (so to speak): Ms. S. paused, issued a couple of quiet “ohhs,” and said the sentence Crotwell will never forget: “Wait a minute — why would my printer be … uh, you didn’t mean for me to go to your computer, did you?”
That’s right, gang: Ms. Schmidt misinterpreted “My Computer” to mean Crotwell’s actual computer — not the Windows icon on her own virtual desktop.
“She took it literally and just went straight down the hall to my computer,” Crotwell chuckles. Once he realized what was going on, Crotwell got Ms. Schmidt back on track and wiped out her problem in no time. These days, you can bet he’s a bit more careful when choosing his words.
“It really cracked me up,” Crotwell says. “It’s easy to take for granted how something second nature to us can sound completely different to a user.”
Stupid tech support trick No. 2: Finding the perfect pitch
Effectively communicating with clients is a common challenge of customer support, especially when help is being provided over the phone. For Michelle Fiske, a productivity consultant at PC Helps, the challenge recently reached new heights — and forced her to drop to a new low.
Fiske was working with an older customer who didn’t have the best hearing. No matter how slowly she spoke or clearly she enunciated, the man couldn’t make out a word she said.
Maybe it was intuition, or maybe it was a matter of experience with her own golden-yeared relatives, but Fiske was struck with a revelation: She realized the high pitch of her voice was probably the issue. She tested her hypothesis in the most scientific way she could come up with — you know, doing her best Brad Garrett impersonation. Sure enough, it worked.
“He sort of laughed at me and said that it was much better and he could understand,” Fiske remembers. “He seemed surprised I could get my voice down so low like that.”
Fiske conducted the rest of the call using what she describes as her “deep demon voice.” She says it was tough to remain professional while sounding so silly, but despite smirks and curious glares from coworkers, she stuck it out and solved the gentleman’s problem.
“As it was happening, it occurred to me how strange it must seem to others,” Fiske says. “He had already said that the deeper voice was better, so there was no going back.”
Stupid tech support trick No. 3: The case of the IT ghost
Any IT pro will tell you that remote access can be a real lifesaver. But sometimes, taking control of someone’s computer from afar can have unintended consequences.
Just ask Russ Long, the IT director of SDS Pharmacy, who was remotely troubleshooting a new point-of-sale system at one of his company’s stores on an otherwise ordinary day. He hopped on the phone with the store’s manager and signed into the system to see what was up. Long was on the brink of resolving the issue when he encountered another problem he’d never anticipated.
“I heard a scream on the other end of the phone,” Long recalls.
Long’s first thought was that the store was being robbed. A moment later, though, he discovered it was something far more amusing actually going on.
“The person working the register started yelling that the computer was possessed,” Long says.
Apparently, the notion of remote control was new to this associate. Long says it took a good few minutes to calm her down and convince her he wasn’t a rogue spirit invading her screen. He admits he had to mute his phone a few times to keep his laughter from being heard.
“Her reaction was just priceless,” he says. “I only wish I could have seen her face.”
Stupid tech support trick No. 4: The runaway mouse
You work for an IT support group — specifically, the escalation team that deals only with the toughest of cases. You get a call from a customer who can’t get her mouse to click. What do you do? That’s the seemingly simple question Ryan Palmertree faced a few years ago.
Palmertree, now a product support manager for Bomgar, was supervising a technician when the call came in. Palmertree and his tech went through all the usual paces and quickly found that the customer’s mouse worked fine in every regard except for clicking. Puzzled, Palmertree put on his detective cap and started to listen extra closely.
“I noticed that whenever she tried to click something, I’d hear this faint little plink sound,” he explains.
Thinking fast, Palmertree told the tech to have the customer put her phone near her screen and click a few more times. Knowing that the woman had a CRT monitor, he began to formulate a crazy theory.
“The next click, it was clear as day — a hollow plastic-hitting-glass kind of sound,” Palmertree says. “From there, it was just like, ‘OK, we’re done here.'”
The woman, if you haven’t figured it out, was physically touching the mouse to her screen every time she wanted to click — a scenario no amount of technical troubleshooting could solve. Thankfully, good old-fashioned sleuthing (not to mention some supersharp hearing) helped Palmertree crack the case.
“It was one of those things where you say to yourself, ‘Wow, did that just happen?” Palmertree laughs. “I was definitely pretty shocked.”
Stupid tech support trick No. 5: A bittersweet jam
One of the most common tech support complaints has to be the office printer jam. Let’s face it: Even in an ideal environment, those things are practically made to break. Throw in high-volume use and low-care users, and you have a made-to-order recipe for disaster.
Keith Brooks thought he’d seen every type of printer jam possible — until one day when he was working as a network support engineer for a large Wall Street firm. After a series of frantic calls — “OMIGOD, WHY CAN’T WE PRINT ANYTHING?!” — Brooks journeyed to the office to see what was causing the trouble.
He got to the problematic printer and ran through the standard series of troubleshooting steps. Toner in place? Check. Cables properly connected? Done. Paper’s all where it should be? Uh huh. So what next?
“The only thing left to do was to shake it to see if some bit of plastic [was] clipped off or loose,” Brooks says. “And sure enough, I heard something rattling around. It sounded rather big, too, [with] loud clanking noises.”
As Brooks quickly discovered, hearing something and finding something are two very different things. He rocked the printer gently and managed to force out some hair, some dust, and a couple of staples — but those lovely ingredients were far too light to be the culprit.
So Brooks got back to shaking. He turned the printer upside down and rocked it harder. Still nothing. Where was this damn thing? Finally, he heard a piece moving closer to the printer’s edge. A little more shaking, and — at last! — the beast behind the jam popped out and rolled to the ground.
Brooks set down the printer and looked to the floor, expecting to see something the size of a boulder. Instead, he saw — wait for it — a tiny jelly bean.
“Who would have thought?” Brooks asks in bewilderment. “That thing was sitting in there, probably stuck to some piece of metal when it got too hot. When the printer was in energy-saving mode, it probably cooled and got dislodged, then did that all over again every day.”
On the plus side, that area of the office always had a delightful tutti-fruitti-like smell.
Stupid tech support trick No. 6: The network installation mess
Our final tech support blunder has a slightly different twist: In this scenario, it’s not the user but the tech himself who slipped up in a silly way. Hey, it has to happen once in a while, right?
The brave soul willing to share his blunder is Rob Miller. Miller, now an IT consultant in New Jersey, was working as a network engineer at a well-known East Coast university some years back. He had just been promoted and was being sent out on one of his first solo missions: a new network drop install. Piece of cake — or so you’d think.
“The order said the drop was for the janitor,” Miller says. “When I got to the building, I told them I was there to do the janitor’s network install and asked where to go.”
The folks in the building pointed Miller toward the janitor’s closet — which seemed sensible enough — and he got right to work. In hindsight, maybe the notion of putting a network connection next to a floor sink should have been a red flag, but hey, orders are orders.
The afternoon ticked away, and Miller finished up the job. He marched back to his boss and proudly announced what he’d done. Unfortunately, he didn’t get the praise he was expecting.
“My boss seemed confused and said, ‘You didn’t talk to me about the ticket first,'” Miller remembers. “‘How could you possibly have known where to do the install?'”
The janitor, as it turns out, had been hired for a clerical job in the same building he used to clean. The network drop was supposed to be for his new desk — not his old custodial closet. In other words, Miller had some serious cleaning up to do in order to make the situation right.
“It’s one of those things where you get a better laugh after the fact,” he admits.
Luckily, aside from some well-deserved jabs from his colleagues, the misstep didn’t hurt Miller much; he spent another day doing the right install, and the custodian-turned-clerk was able to start his new job without issue. As for the network drop Miller had mistakenly put in the janitor’s closet, the university decided to leave it in place.
“I think the mop and bucket are on YouTube right now, enjoying the extra bandwidth,” Miller laughs.