5 practical tips for managing newly remote teams during coronavirus

Rebekah Monson
Mar 11, 2020 · 10 min read
Photo courtesy of wocintechchat/Flickr

Last year, our teams at WhereBy.Us went fully remote. Our team was already distributed across the U.S., and we chose to formalize this as an operational way to ensure that “solo” employees working alone in various cities had the same habits and access as those who gathered IRL. It also saved us cash, the lifeblood of any startup.

Building a truly remote culture takes time. We haven’t mastered it yet, and we probably never will. Every change in personnel and every change in operations is also a culture change. Company culture is constantly evolving, with or without us managers, and staying engaged with those changes is one of our biggest leadership responsibilities.

It’s true that working IRL has advantages. Colocated teams have more “creative collisions” through hallway chatter or quick coffee breaks. You can tolerate less discipline about documentation because there’s someone nearby who can help folks through an unfamiliar tool or process and face-to-face interruption feels less disruptive to us non-robots. Urgent problems are solved more quickly. Non-urgent issues stay non-urgent for longer.

But, for managers, working together in physical space also means what’s really happening at your company may be less obvious. Gaps are more easily swept out of sight. Work on both operations and culture is less effortful. Remote work, for all of its challenges, can force you and your company to become more intentional, more thoughtful, and more resilient to the challenges of change.

Adopting remote work under duress and during a global health crisis is an especially difficult task. For the past week or so, my DMs and email have been filled with requests for help from those who must rapidly upend their team’s entire way of working together to protect the safety and health of their people. Here are some practical habits that we’ve learned that your company could adapt quickly to ease the disruption.

1. Start with your calendars.

Getting used to the heavy calendaring of a remote team is a big adjustment, but it’s vital. Remote teams must deliberately schedule communication that is easily organized ad-hoc in real life. And, you need much more visibility on when your teammates are available and when you’re interrupting the most important work of all — actually working. All of our meetings are video conferences, and every calendar hold includes one, even if teams happen to be working in-person. (More on video in a minute.) Our team works on weekly sprints and our meetings look like this:

  • All-hands kickoff: We devote 15 minutes for the company to get oriented to the sprint. We review the roadmap and identify urgent blockers, update the company on anything the executives resolved over the weekend, and answer any questions submitted to our anonymous AMA form.

Try specific time blocks for cross-team work. Your people need to work together, and they need some dedicated time to make it happen. When we started off, we set two two-hour company-wide internal calendar holds to ensure teams had dedicated time to collaborate on tasks like research, workshopping, brainstorming, and critique. We asked team leads to set these meetings on Fridays for the next sprint and whatever time was unused by Friday close of business was free to be scheduled over.

2. Default to video on and write everything down in meetings.

When we started working remotely, I consulted some friends at Vox and Zapier for advice on how to do it right. Two of the most important things I learned were to default to video on and to get great at written communication.

Rebekah working in her home office
Rebekah working in her home office
My remote management style is shoes-optional, documentation-required.

As a manager, it’s your job to ensure these things happen and set the tone for each meeting. Turn on your camera. Ask everyone to do the same. You need to read people’s faces and body language, so you need those visual cues. Set up your agendas. Take notes in shared docs yourself first to demonstrate how it’s done and then you can pass the responsibility around. (Managers should always stay in the scribe rotation. Ours is a service job. Don’t do it alone, but don’t get lazy either.)

Over time, we’ve grown a little lax on the video rules from team-to-team and meeting-to-meeting, but the notes habits have only deepened. Remote teams have to write. They have to communicate very well to overcome distance. They need written records of decisions to help people get onboarded and stay on top of the work. Documentation is imperative to making all this work, and that includes meeting documentation.

If you’re managing remotely for the first time, some of the first things you’ll identify are your documentation deficiencies in your systems and processes. To get started on fixing them, keep a shared list of documentation needs and start knocking them out as sprint tasks for yourself and your teammates.

3. Leverage asynchronous communication.

Remote work requires deep trust in your teammates. To get the best performance out of your team, you need to care less about when or how they work, outside of your internal agreements on work times, reporting responsibilities, etc. If you manage mostly by hovering, you’re going to have a hard time with this transition.

Asynchronous communication is an asset. People are different. Some work better first thing in the morning (🙋‍♀️), others are night owls. People have different family responsibilities and different personal responsibilities too. Remote work allows for flexibility to accommodate these differences, and that is an advantage for your whole team.

We have set “work hours” for the company when we expect people to be mostly online, but we are extremely flexible about this from team to team and employee to employee. Some people need more structure to stay on track. You can adjust for that too. It’s a good idea to check-in on productivity during your 1-on-1s.

Just your basic Slack dialog for standups.

I built a Slackbot for standups¹ that we have adapted over time to understand the basic daily check-in items: What did you do today? What are your next steps? Are you blocked on any work?

We now send it out at the end of the day and we added some new questions: What were your wins today? What did you learn today? The timing encourages folks to end their day at a reasonable time and the questions encourage us to end our day thinking about what we accomplished and what energizes us.

And some days are really hard. I think we’ve gotten more honest about this in our notes too, which is a good thing for our culture. I also think we learn a lot more about each other. My colleagues are learning about cooking, languages, history, they’re going to cool events, training for stuff, coaching, and mentoring, and doing all sorts of things that may or may not be entirely work-related that help them grow. They inspire me daily.

Mostly, encourage more communication than anyone thinks is necessary. If you use a chat tool like Slack, post notes about when you’re offline and encourage people to keep their statuses up-to-date and to respect the statuses of others. If someone’s working weird hours, have them set up an email responder about when they’ll return. Trust and adjust.

4. Normalize AFK and “heads-down” time.

Asynchronous communication can also lead some people toward burnout. No one can be “always-on.” As a manager, you set the tone for how your team understands the culture around this. Your habits will become the habits of your team.

Send a message and set your status when you’re stepping away from keyboard to take a walk or pick up your kid or to eat your lunch. Let people know when signing on early so you can leave early. Turn off notifications and update your status when you need to ignore Slack for a few hours and focus on your tasks. If something is truly urgent, we all have phone numbers in our profiles. Calling or texting is an escape valve, but in my experience, most issues can wait until you’re back.

5. Engineer some collisions.

No one’s running into each other in the hallway when you work remote. As counterintuitive as it seems, you need to schedule some interactions for your team that aren’t about work. That can start as simply as reaching out to plan digital “coffee breaks” or quick catch-ups with your teammates.

Last year, we started a new routine called What’s Been Up Wednesday. (I’m currently revamping this a bit, but we’ll pick it back up in the next week or two.) Everyone who wants to join can come into a Zoom for a half-hour at the end of a Wednesday and share what’s been going on in our lives outside of work. We also do staff recs — what shows, books, podcasts, etc. you’ve gotten into lately.

Through this little moment, we’ve learned so much more about each other’s passions, personalities, and families. We’ve built a little more camaraderie in our team and I think it’s helped us all see each other as whole people rather than just coworkers.

We’ve also started a lunch and learn series in which every month or so we invite experts, advisers or people we admire to share about their work. These conversations allow us to collectively turn our gaze outward, broaden our thinking, and learn together. And, they give us great ideas to get excited about and plot to steal.

Dungeons and Dragons dice
Dungeons and Dragons dice
The dice hoarding has begun. And I lined this old cigar box with felt to turn it into a dice tray that I can take on work trips. DND obsessions get real really fast y’all.

One of the best social things that happened to me personally this year has been getting into a weekly online Dungeons and Dragons game that my colleague, Michael, started organizing within our company. A few of us play weekly, other colleagues pop in and out, and of course we’ve made new friends outside the company through the game too. Turns out a few hours of grown-up pretend every week is very good for my heartbrain. If you’re not quite as nerdy as we are, consider hosting some Pictionary or Jackbox over a video call. Or play together online. Or maybe set a book club or cooking club for your crew.

I have a hard rule about “no forced family fun,” so all these activities are entirely optional. Optionality protects people who are currently really busy, have other commitments, or who simply don’t want to socialize. That’s OK. Not everyone is a joiner, and there are other ways to engage.

We have “squad” slack channels for (work and recreational) reading, games, music, and more. We have “steal-this” channels to highlight other work we admire. We share a lot of memes and gifs. We ask each other a lot of “dumb” questions. People plan meetups when they’re in each other’s cities. Encourage chatter. Be the first to reach out. Risk looking dumb. Risk being vulnerable.

I truly hope your teams are not affected by COVID-19, but emergencies aside, most companies, especially media and tech companies, require at least some remote work these days. If you’re forced to adapt now, perhaps some of these tips will help you improve your habits or at least think differently about how your team works remotely. I’d appreciate your tips and suggestions on how to improve too. Running a company — remote or otherwise—is an intense learning experience. I would love to learn from you.

Rebekah Monson is co-founder and COO of WhereBy.Us, a media tech startup that is currently crowdfunding. Learn more about the company and how to invest at republic.co/whereby-us.


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Rebekah Monson

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News, supposed insights, and ideas from a group of weirdos building stories and experiences for curious locals.