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Running Out of Things to Say On Zoom? This Communication Expert Wants to Help. Some advice on walking the line between glib and gloom when you're asked "How are you?" 500 times a day.

By Frances Dodds

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The global health crisis has transformed innumerable social norms. But where everyday pleasantries are concerned, none has taken on more weight than the question: "How are you?"

Pre-crisis, the question filled dead air in transient, superficial moments. Unless it was your mother or your best friend asking, the polite thing to do was to answer in the noncommittal spirit of the question and keep things moving. Hitting the right note required a cheerful but not overly affirming response like, "Alright!" "Pretty good!" "Can't complain!"

If you went too far in one direction — a deflated "Okay," or a vigorous "Great!"— then the asking party would be forced to stop and say, "Just okay?" or "Why so great?" For us emotionally transparent types, slapping on the fake cheer was painful, but not as painful as explaining our existential Tuesday blues to Steve in accounting. So "Alright!" it was.

Then, everyone got marooned indefinitely in their respective quarantines. "Now when people are asking it they're actually trying to get a real answer, because we're not going anywhere," says Jill Schiefelbein, a communication strategist and founder of consulting firm The Dynamic Communicator. "We're sitting on the opposite ends of the video screen, and people are wanting more than one word in response. A lot of people are opening up a little more than they used to about how they're really doing because it's become acceptable to do so."

It's really great — necessary, in fact — that people are connecting on a deeper level. The thing is, many of us are connecting with a lot of people. There are morning meeting Zooms, and work happy hour Zooms, friend happy hour Zooms, surprise birthday Zooms, gender reveal Zooms, weekly family Zooms. Because everyone assumes no one is doing anything, we all end up doing quite a bit, and, as one friend told me, "Frankly, I'm running out of things to say."

Schiefelbein is here to help. She says that living a zen Zoom life is a delicate balancing act. And the first thing we have to accept — if it wasn't obvious — is that no, Zoom is not like hanging out in real life.

"When we gather in person, there's typically some kind of stimulus for conversation," she says. "You would be physically sitting in a shared space. If you went out to a restaurant with your family you'd be commenting on the decor, on the menu, on the food. Then everyone would kind of rotate, talk about whatever was going on that week."

The thing about chit chat, Schiefelbein says, is that for many people it's a doorway into deeper connection. "When you hear the word small talk, you think of, you know, trivial questions that fill the space. But small talk is also our way of feeling someone else out and figuring out how much is safe to disclose."

Give your virtual gatherings a little direction

So Schiefelbein's first suggestion is to structure your hangouts around a common stimulus. "When we're gathering virtually, the stimulus we have is only what we can see on the immediate camera. And that changes things. So you will see more success with gatherings that are around a specific theme, a specific challenge, a specific event, a specific activity."

For example, Schiefelbein's friend group has a weekly cooking challenge, where they have to make the most creative possible dish using one common ingredient. "Whoever wins this week picks the ingredient for the next week, and even though we can't taste each other's dishes, we're showing pictures, we're eating together, we're doing something around this common challenge."

The most important thing about having a shared stimulus, Schiefelbein says, is that it doesn't immediately force soul-searching conversations. "We're talking about the dishes we made or the frustrations we had in getting ingredients or something very specific, but it doesn't force us to dive down into the deep, deep levels of inner self-evaluation and reflection, which the majority of people are not comfortable doing."

Related: 25 Ways to Make Your Zoom Meetings Awesome!

Instead of dumping frustrations, diffuse them

While many of us may not feel comfortable sharing our emotions right off the bat — maybe we don't like being vulnerable or feeling like a burden to others — Schiefelbein says it can be good to create a structured space for venting. "The reality is we are doing double, triple, quadruple duty to what we used to do in our regular lives," she says, "And we're also lacking a big portion of socialization and stimulation that we're used to. It's probably not super safe to always be venting to the one person you're quarantined with, or if you're quarantining solo, then the one or two people you trust the most." In other words, diffuse your frustrations strategically instead of dumping them on the same person all the time.

"I have a client in an industry that has declined more than the average industry has right now, and things are getting depressive," Schiefelbein continues. "So I said listen, we're in this time that is unparalleled, and sometimes we need to know our managers are experiencing crap too. So at the beginning of a meeting, just be honest and say, "Listen, everyone, I know these team meetings may be getting a little routine, but I also know that it's important to check in. That being said, some things just plain suck right now. So I'm going to go first and I'm going to tell you something that is really frustrating me and each person on this line gets 45 seconds to vent about whatever you need, no matter how trivial it may seem. Before we do this, raise your hand if you agree that we are going to be judgment-free. All right?' And then after you go around, you immediately follow that with something everyone is feeling positive about. Rapid fire around the room, things we are grateful for. Air conditioning, WiFi. A laptop with an extended battery, whatever it is."

Hearing what a wider range of people are going through, as opposed to the one or two people you usually share your troubles with, can make you feel less alone.

Set boundaries around your time and energy

As noted earlier, everyone being stuck at home has, for many, resulted in a kind of enforced busyness. Because people assume you don't have anything going on, they feel more entitled to your time. This is not good.

Schiefelbein says, "I have a client who was showing me her meeting calendar every day and she said, "I had a lot of meetings before this, but now that I'm not in an office, it is absurd how many people feel they need to meet.' Her calendar is literally full from 8 a.m. to 5 p.m. or later. She doesn't even have time to get up and go to the bathroom cause these meetings are back to back. It's not sustainable, and I know she's not the only one facing this."

There are a lot of conflicting feelings going around. People feel a responsibility to show up and be supportive for their loved ones, and in a workplace setting, to prove their worth. But all of these interactions can also be very draining, not to mention that getting anything else done requires double the usual concentration. "You have to be willing to step up and communicate what you need," says Schiefelbein. "And right now I see a lot of people not being very honest about what they need."

If you have a standing weekly Zoom hang with your friends or family, Schiefelbein says it's not a bad idea to set expectations. "Say, "Listen, can we agree that we all have the right to bail out of this if we just need some "me" time? But in the same vein, can everyone agree that if any one of us really needs everyone there that night, we are all going to make an effort?'"

Everyone is experiencing this time differently, so it's important not make assumptions about what someone else is going through. It's good to create opportunities for everyone to talk about their feelings, but it's also okay to just do something fun and forget about our worries for a while. With that in mind, Schiefelbein put together a little list of suggestions for themes and activities to get you gabbing on personal and professional Zooms.

Related: 6 Tricks You Need to Know About Zoom

Family and friend virtual gathering prompts

  • What's your favorite vacation memory? Bonus points for bringing a picture or souvenir.

  • Meme or GIF scavenger hunt: Everyone in the gathering rotates picking a theme and everyone goes out to hunt the funniest meme they can find and bring back to share.

  • What's the restaurant or bar you miss going to the most? Bonus if you can get that delivered or try to create that meal or cocktail at home.

  • Pick a game! There's online trivia, Cards Against Humanity, escape room and many other options that you can play together, while apart. (Entrepreneur editor Jessica Thomas says her family has been using the game apps Quiplash and Kahoots and recommends the app House Party for connecting to all play games together.)

Sprinkles of fun for business team virtual meetings

  • Renaming Games: Have every team member rename themselves to their favorite...(childhood cartoon character, cereal, sports icon, movie star, bucket list destination, etc.--the possibilities are endless) and then call everyone by that name during the meeting.

  • Creative Coffee: Have a coffee mug show-and-tell (or any beverage glass, for that matter). Most can find a fun, memorable or funny mug, glass or stein to use for a meeting. Show them off and let each team member share a memory associated with where they got it.

  • Improv Games: Get your team collaborating and thinking quickly by incorporating improvisation games into your meeting. An easy one to start with is "word at a time" where each person says one word and you have a goal of completing a thought or story.

  • Virtual Art Challenge: Divide your team into pairs and have them work together to create the most impressive whiteboard artwork they can in a limited time frame. For example, you have five minutes to create a work of art on the whiteboard with the theme "favorite foods" (you can insert any theme related, or not related, to your workplace). And then have a vote!

Related: Working Remote? These Are the Biggest Dos and Don'ts of Video ...

Frances Dodds

Entrepreneur Staff

Deputy Editor of Entrepreneur

Frances Dodds is Entrepreneur magazine's deputy editor. Before that she was features director for Entrepreneur.com, and a senior editor at DuJour magazine. She's written for Longreads, New York Magazine, Architectural Digest, Us Weekly, Coveteur and more.

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