This Is How To Be a Better Communicator Online and Off, According to a Conversation Expert

I fancied myself a good online conversationalist—until I met Celeste.

Photo by Christin Hume on Unsplash

Let’s start with the obvious: the way we communicate today looks wildly different than it did even five years ago. Sometimes, picking up the phone to call a friend seems more like a “back in the old days” story you’d tell your grandchildren, rather than a viable, present-tense way to connect. It doesn’t help that technology makes it possible to get everything you could ever need (groceries, toilet paper, clothes, movies) without ever talking to another human.

If the old maxim of practice makes perfect is true, you can only guess what this is doing to our face-to-face communication skills. Even if we think we’re doing okay adapting to a keyboard-based conversation economy, we’re probably not doing as well as we think. For example, I fancied myself a good online conversationalist—until I met Celeste Headlee, conversation expert, viral TED talk giver and author of the forthcoming book We Need to Talk. Even though I type "haha!” instead of “LOL” because it feels more human, never sink so low as “....” and insert a generous dose of emojis to lighten any mood, Headlee told me (via email) that no matter what lengths I go to to make digital communication feel less, well, digital, “online conversations aren’t really conversations.”

And she would know: Headlee has been researching how people talk to each other since 2009. It all started after she became co-host of the Public Radio International show “The Takeaway.” In researching how to ask better interview questions, she found the skills she learned were applicable to situations far beyond the radio world.

Headlee shared some of these skills with me and demonstrated her mastery of them in the process—she emailed me early on a Sunday to say she’d respond to my questions later in the day with more thorough answers, and lo and behold, she stuck to the schedule. (I’ll be trying this strategy in situations when I need a few hours to mull over a response.) While she noted that texting and tweeting has changed how we talk to each other (mostly for the worse) she emphasized that if used correctly, technology can be a gateway for authentic, good old fashioned, IRL communication.

Here are Headlee's best insights to help you make conversation on and offline more meaningful.

1. Face-to-face conversation is hard because it’s supposed to be
I asked Headlee what makes for a good conversation and she responded that conversation isn’t about “basic exchanges of information: what do you want for dinner, pizza, OK, sounds great.”

Instead, honest-to-goodness conversation is “any exchange that includes nuance and a possibility for misunderstandings,” she wrote. And while digital convos are ripe with the potential for crossed wires (ask me about the time I accidentally scheduled a date with the wrong unsaved phone number), part of why online conversations can’t really get deep enough is that they’re missing two of the three pillars of analog human communication: facial expression and body language. (The third aspect is words, “the meaning of the vocabulary and context in which they’re used,” Headlee wrote. And while online chats obviously have written characters, think of all the ways autocorrect, abbreviations or badly timed emojis have twisted your intended meaning.)

“Many people believe that they are more connected to family and friends than ever before and that couldn’t be farther from the truth.”

2. Online conversation is the appetizer, not the entree
Digital chats should be small talk leading up to bigger, better connections over the phone or in person, according to Headlee. The “occasional text to relay information (my plane lands at 4:15) is great,” she wrote. But remember that “online communication is not authentic connection. It’s a wonderful tool to start the process of conversation and connection, but nothing replaces good, old, human, face-to-face meetings.” 

Part of why Headlee cautions against digital chats as a primary form of connection is the false sense of closeness they give us. It may seem like an online exchange brings us closer with people far away, but it’s a mirage-in-the-desert scenario. Celeste wrote, “many people believe that they are more connected to family and friends than ever before and that couldn’t be farther from the truth.”

3. You need to accept that online communication has limitations
Headlee told me that there are a few things we can do to avoid miscommunication and open dialogue for offline conversation: “The best online conversation is one that accepts the limitations of the platform and doesn’t attempt to convey emotion or nuance.” Using texting or Tinder for “complicated conversation is very problematic,” she wrote. Texting—including emojis—also “makes us think we’re communicating more effectively than we are,” she wrote, but added that she still uses smiley faces because they are a powerful symbol. That smiley won’t work if you’re trying to win someone’s favor back though: “Never say you’re sorry with a text or email,” she wrote. “Pick up the phone.”

"We are using tech to avoid entanglements with other humans, but it's the entanglements that make relationships so interesting and rewarding.”

4. Tech gives us license to throw social boundaries out the window
I asked Headlee what’s changed in conversation today versus a few decades ago. She summed it up perfectly: “One of the biggest changes is that people tend to trample social boundaries now.” This can range from sending unsolicited pictures to contacting people at all hours of the day and night. Technology “encourages people to text or email at times that we never would have dreamed of calling on the phone,” she wrote.

5. Ghosting and trolling belong in the same category
Ghosting has existed long before technology, but it was “much more difficult before 1990,” Celeste told me. “If you met someone through work or a mutual friend, it was very hard to simply never call them again without repercussion. Ghosting is simple now, but it's no less rude and hurtful.” She adds that ghosting is a symptom of many changes in conversation that are negatively affecting us: “Trolling online is possible because of anonymity and convenience. Same for ghosting. We are using tech to avoid entanglements with other humans, but it's the entanglements that make relationships so interesting and rewarding."

That’s the takeaway here: we’re using technology because it’s easy, because it strips down complicated feelings and truths into 140 characters or a thumb swipe. But it’s the messiness that we should look to regain, because it’s what makes connecting truly human.

“Trolling online is possible because of anonymity and convenience. Same for ghosting."

Once you’ve summoned the courage to actually talk to another human face-to-face, here are some tips to make the process a little easier.

1. Having a good chat IRL is as easy as 1, 2, 3
This one is short and simple: good conversation is built on understanding what someone told you, making sure you’re understood and learning something from the other person. Voila, you know how to have a great conversation!

2. Small talk isn’t a waste of your time
Contrary to my previous beliefs (and maybe yours), Headlee said it’s a mistake to to think casual chit chat isn’t worth the effort. “Small talk is meant to help us find common ground and establish bonds of trust,” she wrote, adding that online communication is actually fine for that. If you’re like me and would rather pick up a pretend phone call instead of engaging in pleasantries, there’s hope for you yet. Headlee recommends that chat-avoidant people “practice small talk every chance you get, starting with the people at stores and coffee shops who are trained to be friendly and responsive.” If that’s not convincing, maybe science will change your mind: Headlee wrote “there is a large body of scientific research that shows small talk is good for your brain and your mental health and physical health. One study showed people expected to hate chatting with strangers on the train but ended up enjoying their ride more when they were forced to chat.”

3. Surprisingly, pretending to spot someone you know and then briskly walking in that direction isn’t the best way out of a conversation
How do you end a conversation? Make it clear you appreciate the person’s time, especially if they’ve been open or vulnerable with you. Finally, make plans to talk again, then actually keep those plans. “Don’t promise to call in a couple days and then not call,” Headlee cautions.

As someone who is notoriously bad at getting out of conversations without making a scene, I followed up with Headlee for more insight. Specifically, I wanted to know how to end a conversation with someone I didn’t want to call in a couple of days. She wrote that if we see acquaintances like that on the street “and don’t want to talk, just say ‘it’s been great to see you. I’m sorry I have to rush off.’”

If that makes you feel uncomfortable, you’re not alone. But keep in mind that it’s possible to be honest “but remember that life’s too short to be needlessly mean,” Headlee wrote.

My back-and-forth with Headlee revealed that when it comes to conversation today, most of us don't know what we're doing. But it was also optimistic, especially in terms of simple things we can do to have better conversations on and off line. 

And there’s at least one easy way to start today: Pick up the phone. “We spend 26 minutes a day texting and only 6 minutes on the phone,” Headlee wrote. “Use your smartphone for its primary purpose. Human beings, by evolutionary design, are incredible communicators. We are born with miraculous gifts for talking and reading facial expressions and body language. We are designed to communicate face-to-face.”

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