Culture — March 24, 2021

Checking in: Looking Back on a Year of Connecting Remotely

Since March 27, 2020, Cake & Arrow has been “checking in” each morning over Slack—a practice worth trying—whether your team is locked down or co-located.

by Kate Muth

Digital Culture Future of Work remote work

a screenshot of the gallery view of company Halloween zoom

On October 31, 2020, Shawna dialed in for Cake & Arrow’s weekly all-hands from outer space. Wearing a silver jumpsuit with NASA insignia, with a convincing shuttle cabin Zoom backdrop behind her, Shawna looked every bit the cosmic voyager she gamely meant to embody. Like the rest of our team that day, she was leagues away, but she beamed in, shiny and present through the magic of technology. 

A screenshot of Shawna on zoom dressed as an astronaut with a spaceship background

Then the rest of our gallery flickered into focus: The Tiger King and Daniel Tiger, a lobster, a “shih tzu in a knife fight,” Hamilton, someone from Krypton, Twin Peaks’ Log Lady—all and sundry characters. Our Zoom grid that day was a bizarro simulacrum of Cake & Arrow’s annual Halloween tradition, when we draw names and then select the costumes that we believe best represent the ineffable substance and spirit of our C&A crewmates.

Most years, we don these questionably-fitting get ups, avoid embarrassing eye contact on our subway commutes, and pass the workday together in character. With faith in our clients’ good humor, we suppress giggles to present wireframes from behind Joker masks, or report research findings over the whir of the inflatable dinosaur suit’s fan. And then we head out for an early happy hour, a ragtag crew exalting in our silliness together. 

Culture shocked

Before the stay-at-home orders, early last March, if we talked about our workplace “culture” we likely talked about how well a potential hire’s quirks might mix with the house blend, or where to book the holiday party. 

Then, we rarely discussed our real culture, which flourished in the air we breathed and at the lunches we shared. The culture that nourished itself daily on a diet of casual interactions—the inside jokes, the high fives and hugs, the spontaneous cheers, and the rare, but poignant tears. We’re proud of, and known for, this culture at Cake & Arrow. Contractors share that “out of all the places I work, you guys are my faves—such a nice vibe.” And note that as a freelancer, “it’s not often that you feel really integrated into the team.”

But in less than a week, as the Covid-19 pandemic sped from rumor to reality, we packed in all our shared proximity and experience and headed home to work, heads down, in our separate spaces—little guessing that a year later, we still wouldn’t know when the office would feel like a safe space to share again. 

And by October 2020, we were months into working from our bedrooms and resigned to keeping our Halloween tradition with Amazon Prime costume delivery and tequila shots spilled over Zoom. Was it the same? Not at all, but surprisingly, it wasn’t so far off. And that was because throughout several seasons of enforced remote work, we’d improbably managed to maintain and even strengthen our bonds.

As user-centered designers, we strive to understand and observe people over time. We do the work to see what their days and weeks and years are like, where they’ve been, where they’re headed, and what attitudes and associations they bring to the relationships they build along their journeys. We realized that the same design thinking we use for our client work applied to our pandemic challenges. To maintain the ties that create culture, we needed to design for both routine and spontaneity. We couldn’t force relationships, but we could, by design, create the conditions in which they could blossom. We couldn’t make people connect, but we could invite them to “check in.”

Time to check in

A screenshot of a Slack conversation

Introducing a daily check in to our “general” Slack channel was a natural extension of established Cake & Arrow practices. To kick off a new client engagement, or to start a collaborative design thinking workshop on the right foot, C&A facilitators often begin with an “ice breaker” question designed to make sure attendees are dialed in to the here and now happening in the room. The questions are often spontaneous, simple and sometimes offbeat—but they always do the job. “What ‘structure’ are you thinking about?” I was thinking about an outrageously painted parking garage in my hometown. “What are you excited about?” “Not being in this meeting.” Honesty is always encouraged and judgement withheld.

Without much effort, we found that ice-breaking “check in” moment translated easily into Slack, and we’ve been doing it every workday since mid-March. Each morning, I type “@here Check in…” and the day’s question into our “general” channel. 

It’s not perfect—I’ve been late posting the question, Summer Fridays were low participation, I’ve definitely phoned it in (“best pizza topping”), and to my great regret, I’ve missed a day or two outright. But as the pandemic days marched on, the daily check in has become a constant in our workday culture. We’ve shared baby pictures, go-to recipes, recurring dreams, astrological signs, childhood preoccupations, hopes and dreams. It’s helped us to sync up the rhythms of our home lives, and connect to one another by sharing the milestones and memories that have made us who we are.

What we’ve learned

A question about nicknames led Jess and I to the surprise that we were both raised by telecommunications professors who taught us more about broadcast call letters than we had any business knowing—I shared that my dad called me “KDKA,” and Jess replied, “you mean like the Pittsburgh radio station?”

Later, when we shared our first concerts, the conversation helped Lisa and Emily discover that they’d both been at the same Rilo Kiley concert in 2003, with mutually regrettable hairstyles. And Jen and I realized that we had musical tastes more in common with some of our Gen Z coworkers’ parents than our teammates themselves. My parents took me to see Peter Paul and Mary. Shawna’s mom took her to see Foo Fighters.

Meanwhile, Emily and I, through a roundabout route, discovered that we are likely related by marriage nine generations back. And Mark learned that other people are actually showering and brushing their teeth during quarantine. Go figure.

A Slack conversation about genealogy

By Halloween, when it was time to choose those costumes for one another, we had plenty of personal insights to draw from. For example, we knew that our astronaut Shawna loves jumpsuits—“what item of clothing is your favorite right now?”—and had a good friend get a job at NASA—“share some good news….” 

And even more months later, we’re all still using Slack to radio ground control and each other. “Houston, do you copy?” Our morning Q&A affirms that yes, we’re all still here, we’re checked in together for the day.

How to check in

Checking in is easy. All you need is a shared communication channel—Slack, Yammer, Teams, or whatever—and someone to emcee the questions each morning. Try to keep the timing consistent—I aim to get ours posted by 10am—but better late than never. And resist the impulse to co-opt the check in question for “work stuff.” Save project blockers and OKR progress for team stand ups; keep check ins light and social.

For us, the questions started and remain simple, but, over the days, weeks, months, and now a year, some general rules for a good check in have taken shape:

  • No cheating—sure, you can google “awesome ice-breakers,” but where’s the love in that?
  • Avoid repeats, a meh original question is better than old news.
  • Always answer your own question to help set the tone or illustrate the intent of the question
  • Ask questions that require more than a “yes” or “no” answer—the conversation, stories, and details are what make check ins human and fun
  • Personal questions are ok, but stay away from anything too heavy or too dark, and always give people an out.
  • Try not to tease, and never pile on.
  • Don’t sweat it if people don’t answer. There’s always tomorrow!

And we’ve identified some some winning, evergreen themes:

  • Seasonal and topical:
    • Best Fall sensory experience (kinda weird, but try it).
    • Best Halloween candy
  • Personal favorites:
    • What’s your daily beverage? Coffee at home, from a shop, Chemex, tea, gin, etc.
    • Best sandwich
    • How do you like your eggs?
    • Tell us about your favorite grocery store.
    • If you could live in any fictional world, which would you choose?
  • Flashbacks & nostalgia:
    • Your favorite or most influential teacher.
    • School picture day. Share them if you’ve got them.
    • Something you do today that your 15-year-old self would never understand.
  • “Would you rathers,” and other hypotheticals, in a pinch:
    • Cliffs of insanity, pit of despair, fire swamp, ROUS, Lightning sand, iocane powder, dueling Inigo, or wrestling Andre the Giant. Pick your poison.
    • Would you rather give a 60 minute impromptu presentation or realize that you have a 10 page paper due in 24 hours?
    • You win the billion dollar lottery, but you have to stay in one place for the rest of your life (no travel). 1) Do you accept your winnings? 2) Where do you choose to live FOREVER?

And we’ve found unique ways to keep each other engaged and honest:

  • Accountability challenges:
    • Morning win/loss
    • What’s something you could do RIGHT NOW to make your day better?
    • Share something that you’re avoiding. :grimacing:
    • Weekend pledge, what’s one thing you fully intend to do this weekend?
  • Live updates:
    • What is the dominant sound in your environment right now?
    • What’s happening at your place today? Pics plz.
    • What’s the best thing you’ve already done today?
  • Random “show and tells” that document our days
    • Your favorite mug.
    • Favorite piece of clothing currently in your closet. Pics if you can.
    • What do you collect? Share pics.
    • Ramona (my 8 year old) suggested this one: What is your favorite drawer or cabinet in your house?
    • The most interesting piece of furniture in your home. Pics plz.
  • Humblebrags:
    • Famous people who went to your high school.
    • Little wins
    • What was the coolest thing you had a kid? Like your friends were jealous.
    • Share some interesting family lore.
    • What celebrity do people say you resemble, and how do you feel about it?
  • Personal quirks:
    • A boring fact about you
    • Your biggest vice (if you dare!)
    • Tell us about an interesting job you’ve had, besides this one!
    • Unpopular opinions— name 3 things that everyone likes, but you don’t.
    • Share your nerdiest thing.

My nerdiest thing? I could link you to the spreadsheet I used to track all the Pride and Prejudice fan fiction variations I’ve read, as I did when I responded to the prompt on July 9, 2020. But reflecting today, I can also confess that over the past 12 months, I’ve been happily geeking out as I’ve crafted C&A’s daily check ins. And I can humblebrag that I’m not the only one who’s enjoyed it. A comment in my 6-month 360° review made my year, “Kate’s daily Slack check-in questions bring a lot of joy and bonding in a time that we needed it most. Love that she brought it to us and has kept it up. It’s a highlight of a lot of people’s mornings, and I know she loves doing it too.”

And it’s true—all the feels. You can have them too. Time to check in. Download our list of 199 check in questions.

199 Ways to Check In

Questions to break the ice, strengthen bonds, and bring teams together.