"Hey, Can You Help Me Log On?"

A few weeks ago, my boss called me into her office. She said my name in a tone that meant she was annoyed by some tech issue—the phone-book icon had mysteriously vanished from her BlackBerry, a link wouldn't open, or, in this case, she needed to attach a document to an e-mail. I found her at her desk, scrutinizing the file names of roughly 40 Word docs littering her desktop. She stayed in the chair while I hunched over her desk and clicked away. "See where it says 'attachment'? You click on that, then pick which file you want to attach," I said. I debated about adding this next part, but decided it might help: "There's the little paper-clip picture to remind you that's what to click on, like you'd attach a document with paper clips in real life." I beamed but worried it sounded condescending.

Aside from technology issues, I'm not used to teaching my boss something she doesn't know. Nearly all the time, it's the reverse—my boss is sharp and talented and has 20 years of experience in the industry, so she's obviously the one teaching me (um, that's why she's the boss). I'll admit it feels good to be indispensable to a higher-up, and it's empowering to know something she doesn't. But it also feels a bit like seeing your grammar-school teacher in her underwear—a glimpse of the real, flawed person behind the unassailable facade. I think that's why coaching my boss in basic tech skills is so awkward—because in that moment, our power dynamic is reversed.

Later that evening, a group of my friends assembled at our local dive bar. When the conversation turned to work, I recounted my chirpy paper-clip speech and asked if I'd been helpful or an asshole (or both). Was there any tactful, non-fireable way to teach a hopelessly Luddite boss? Wasn't that like playing a round of catch with your dad and telling him he needs to work on his throw? It turned out most of my friends had had similarly awkward moments. Annie told us about her company's tech-clueless CEO, who didn't know that he could silence a cell phone mid-ring. So he would let his phone blast at top volume—a full 30 seconds of mortifying calypso Muzak—during meetings and conference calls. He'd just say, "Oh, I'm not going to answer that," and let it ring endlessly, even during an important briefing with a senator. Annie said she wanted to show him the "silence" button, but didn't want to embarrass her company's biggest boss by pointing out something that seemed blatantly obvious, so she decided to stay mum. "But then I felt like I was letting him look like a jerk," she said.

Steph added that her boss, who oversees executive-level decisions affecting hundreds of employees and millions of dollars, once called Steph into her penthouse of an office because she was having trouble with her mouse. "The mouse was upside down," Steph said. "The red light was shining up in the air, and she still kept trying to roll the thing on the mouse pad. I didn't want to make her feel dumb, so I just kept repeating, 'I swear, I've done the same thing!'" We all let out a sympathetic sigh and took a swig of our beers.

Then Caroline told us about her approach with her boss, a fashionista who always demanded the sleekest, shiniest new BlackBerry but didn't understand why e-mails she sent from it were getting bounced back as undeliverable. "She was putting 'www' in front of e-mail addresses, like www.jane@gmail.com. So I went into great detail explaining the difference between an e-mail address and a website." Ultimately, the "lesson" just frustrated her boss, Caroline said.

Soon, Erin was unloading about the time her boss was angry because she hadn't responded to a time-sensitive text. Turned out, the boss had sent it to Erin's landline. Was it easier just to take the blame and move on? Stuart said he once found his boss struggling with the computer's calculator function—the boss was jabbing his fingers against the monitor, trying to punch the number buttons like it was an ATM touchscreen. We laughed so hard that Steph nearly did a spit take.

As the laughter subsided, I thought about just how unfunny it can be that the people who sign our paychecks and wield the power to tell us we need to be in extra early tomorrow often can't do remedial tech tasks. I considered one teeth-clenching moment, when my boss asked me to print out a story because she didn't know how to click on a link—and didn't want to learn. As I stapled the stack of papers, I had to stop myself from groaning, "OK, now how about bumping me up from minimum wage?"

That said, I know my generation is on top of the tech heap now, but like everything else, it's cyclical. There's already technology I'm uncomfortable with (a Kindle? You expect me to read an entire book on that tiny little screen?) and the redesigned Facebook news feed sends me on a cranky rant about why perfectly good things have to change; I can't imagine what it'll be like in 15 years when my friends and I are the bosses. After all, the kids who will one day be our assistants were Twittering in the womb.

Back in the office a few weeks later, my boss wanted me to check something on the company's Web portal. Actually, it's a relief when she just asks me to deal with a tech assignment rather than having me walk her through it. She stood by my desk, inquiring about my weekend as I tried to log on to the site. A memo box popped up and told me that my password was about to expire and forced me to create a new one before I could go on, which took about four tries before the computer decided I'd made an acceptable alphanumeric combination. Then another box popped up asking for my key-chain password. With my boss still chatting behind me, I typed in the new password, which made the box shake and display an invalid message. I ended up calling an IT guy, who cleverly advised me to restart the computer. I let out a primal "Ughh," and my boss raised an eyebrow.

"Frustrating, isn't it?" she said.