February 12, 2018

I have a spotty track record of rising to the moment of awkwardness at the office. Once, after being told I was receiving an unexpected promotion, I immediately asked for an increase in compensation to match the increase in responsibilities. I didn’t really know how to ask, and I’m sure I didn’t phrase it in the most eloquent way possible, but I blurted out what I meant, and it worked. The awkward moment? Very much worth it.

But then, there was the time when several people in different parts of the company I worked for privately contacted me to complain about one of my direct reports. This person, they told me, was disrespectful and rude. In our next check-in meeting, I meant to bring this up; I wrote it down and everything. Towards the end of the half hour, I stared down at my notebook, where I’d scrawled something like “address attitude??” in ballpoint ink. But I didn’t know how to say it. So I didn’t say anything.

If social life is a performance, then awkward moments are the unscripted parts.

If social life is a performance, then these are the unscripted moments. We often get plunged into these kinds of cringeworthy situations whether we’re trying to or not, and the uncertainty of it all—how will someone react? Will I say things the right way?—is easier to keep at arm’s length. If you don’t know what to say or do, there’s always nothing. You don’t have to say or do anything. Most people would understand and perhaps even expect you to sense an opportunity but ignore it, because your next move is unclear. But when that’s what you choose to do, you lose your chance to make a move at all.

Here, a few tips to help you push through the awkwardness and say what you need to say.

Address the Awkward Elephant In the Room


Not knowing tends to make people uneasy. Consider a classic 1960s study, for example, in which people received several rounds of small but still painful shocks of electricity. Little warning bells went off several times throughout the study period, sometimes followed directly by a shock and sometimes not. Overall, people told experimenters that they preferred when the warning was followed by the shock over when it wasn't.

For me, this helps explain the social pain of awkwardness, and why one of the most obvious awkward-moment coping strategies often works so well. Sometimes if you just say, "This is going to be a little awkward," it turns out not to be so bad after all. It's nice to get a little heads-up.

Sometimes if you just say, "This is going to be a little awkward," it turns out not to be so bad after all.

For example: Not long ago, I made myself go to a networking event. I know these things are annoying, but they are also annoyingly useful; I've met people at book-launch events or journalism meetups whom I ended up working with later.

At this one, I was standing alone, waiting for my friend to show up, when I noticed another solo woman. "Hi," I said to her, "I notice that you too are standing awkwardly alone." That was all it took to break the ice. We started chatting so animatedly that when my friend finally got there, she assumed this random stranger and I had arrived together.

Forget the ‘Perfect’ Path Forward


But even when we know—and announce to ourselves—that things will be awkward, it can still feel tough to move forward.

An unimportant but irritating example of this is the boss who gave me a nickname I hated. She said the nickname for the first time, and two paths appeared. Either I could have the awkward conversation and say that I'd rather she called me by my actual name, or I could just put up with it.

I spent so much time imagining all the ways I could bring this up that I forgot to ever actually bring it up. And then the thing happened where it had gone on for too long, and with every day, week, and month that went by, it felt like too much time had passed to bring it up now.

I spent so much time imagining all the ways I could bring this up that I forgot to ever actually bring it up.

But sometimes, we have to just pick a path forward while acknowledging that it may be an imperfect path. It's simply the best choice you could make in the moment. It’s a tactic I learned from Alison Green, the author of New York Magazine’s “Ask a Boss” advice column.

After reading Green’s column for years, I think I can distill her advice down to this: In awkward work situations, be as straightforward as possible. Her letters often include variations on this message: The way to address this is by talking to her. Talk to them now. Just talk to her. Do it ASAP, though, because it's going to get weirder with each passing day.

In awkward work situations, be as straightforward as possible.

So you don't know what to say. OK. But you know what's bothering you, right? That's a start.

It's why so many people love Green's approach to workplace awkwardness—she sees direct paths that cut through the ambiguity described by every letter writer. The question may be head spinning, but you read her response and you think, “Of course clearly, that was the answer.” "I've always been pretty eager to tackle the awkward," Green tells me, "but I don't think that's normal behavior on my part."

Those of us who respond to uncertainty at work (and elsewhere) by avoiding it are often imagining all the ways we could make things worse by addressing the situation: We could offend someone or cause tension or just risk looking really stupid.

"So often," she said, "awkwardness is being direct about something that people aren't normally direct about."

She can't tell you for certain how it will turn out once you go the straightforward route, but she thinks it's always better to be honest and ask for what you need rather than hoping in vain that someone will see you struggling and offer a solution. Be direct, she encourages her readers, and remember that this is not the same as being rude. Be as kind as you can, but when it comes down to it, you just have to say the thing.

Excerpted from Cringeworthy: A Theory of Awkwardness by Melissa Dahl with permission of Portfolio, an imprint of Penguin Publishing Group, a division of Penguin Random House LLC. Copyright © Melissa Dahl, 2018.

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