Leaders Eat on Camera: Advice from 10 Years of Leading Remote Teams

Providing leadership can be challenging because it involves people who have their responsibilities and goals in addition to whatever is happening personally. Add in whatever stress might be taking place at home, with family and friends. Being a human is hard enough, so it makes sense that leading them is at least as difficult.

Now put blockers in the middle like restrict when and how you communicate with the people you lead. Or try running a design critique with all of the attendees sitting in front of webcams (and Facebook or email) and no one paying full attention. It doesn’t take a lot of change to disrupt a team’s workflow, energy and culture. Working remote has suddenly become the norm for major portions of our workforce.

Most of us have experience working remotely for a day or two here and there. A vacation that we might have wanted to extend or a sick day spent at home. The one-offs are easy enough to do, but it’s the extended remote work that will have an impact on your team’s ability to interact with others, collaborate with parts of the business, and possibly your team’s culture (something that when damaged can take a lot to recover). My intent here is to share what I’ve learned the hard way by building a remote company and culture and then eventually ending up at InVision, which is also a completely distributed company.

Remember, what works for me may not work for you but I hope these ideas will inspire your own path. And it’s also worth noting that some of my experience involves leaving the house, and I realize those activities might be a bit of a touch-and-go situation depending on your circumstances. No matter how these “interesting times” pan out, I hope that you will find a way to get some fresh air and a change in scenery.

The morning routine and the evening escape plan

Working remote got a lot easier for me when I stopped living like I work out of my house. This meant finding things for me to do before, during, and after work that got me away from my desk. Start your day like you don’t work at home. Get up and ready for the day like you’re about to enter the daily commute. Find your routine, whether it’s taking a walk around the block or listening to a few stories on NPR as you enjoy your coffee.

And without an evening escape plan, it’s too easy to continue working through dinner—and then continue working until bedtime. Make sure your work day ends. Have a scheduled activity to do after work like making dinner with you family, exercising or finishing the last episode of Tiger King.

Standing interaction time

Once one person on the team is remote, everyone has to work like they are remote. This rule includes finding meaningful ways to connect—virtually. With my first remote team, we tried normal activities like happy hour, but they don’t translate as well as a digital experience. After trying different activities like group lunch and open Skype sessions, this particular group found their fun in beating each other to death with “Doom Hammers” during games of Halo. Even on the worst day at work, once everyone had a controller, then laughter followed soon after.

Now, your video game mileage may vary, but the lesson I learned here is that there is a genuine need for the team to interact in a way that has zero to do with work. Here’s a different story from a design team “at-scale”: IBM Design started a radio station that’s streamed behind their firewall. The program is so successful that they now have designers and engineers taking DJ shifts around the world. It now runs 24/7 and features a handful of programs on design.

People first, work second

Your soft skills will get a workout when leading a remote team because you’re not around everyone as much. It’s difficult to “see” how they are doing. Standing 1:1s are a must, and they should be considered sacred (meaning they don’t come second to whatever new meeting pops up). Your face-to-face interaction time is going to drop severely, so keep what time you do have together a top priority. I would also advise keeping an eye out for content to help guide your upcoming conversations to help keep your team calm during this time. NPR typically does a great job of finding subject matter experts who provide suggestions on types of conversations to have with your employees.

Kill all of the elephants, quickly

Radical candor is super hard in person, but I’ve found that it’s still daunting in a remote team. Try to be as transparent as you can without adding to the existing stresses of working distributed. If you “see” something going on, throw it out in the middle and get people to talk about how it makes them feel. Eventually, this should help the team find an opening to move into a discussion about how to tackle the problem.

Remember, focus criticism on the idea, not the person! In a distributed team, the longer elephants are allowed to live, the more risk of toxicity entering the work environment—which is difficult to reverse.

Re-create your working agreement

Working remote means not being able to “drive-by” a desk or run into someone in the hallway or the kitchen. It also means that it’s now possible to re-arrange your workday to adjust for running errands. Take the good with the bad, but consider amending your team’s work agreement, especially around when, what and how you will communicate. Consider looping in your partners and stakeholders to create new expectations. Give your revised agreement a few weeks and then come back as a team to check in and see how the new arrangement is working.

Slack and email ≠ Communication

It doesn’t take much for the volume of messages in Slack (or Teams) and email to pile up. To top it off, most people don’t care enough to practice proper etiquette when communicating digitally. My personal favorite is the three-foot-tall email-chain that’s been going on for weeks until you’re CC’d with zero context, only a “FYI.” Yet you’re expected to digest the “conversation” and make a quick decision.

My next favorite: The impromptu question in Slack that generated a twenty-minute exchange of messages, emoji and animated GIFs that you’re brought into with a simple @gregstorey followed by “scroll up.”

Neither are these exchanges positive nor an effective way to communicate, but they’re done all the time. Talk about communication needs and requirements as a team because you need to develop some empathy for what it’s like to be at the end of that shitstick, and then create a shared definition of what proper communication is and how to ensure it happens.

Without this discussion and decision making, a remote team is always one Slack thread away from turning into Lord of the Flies.

Learn how to eat on camera

This is one behavior I just don’t understand. When we work in person, it’s pretty common to have a meal with your colleagues. When you get into management, it’s common to work through all-day meetings with lunch catered. We eat in front of each other all the time, but take that same team members and put them in front of a camera, and suddenly eating is a no-go. I can understand if folks don’t want to start a Twitch channel and sit in a gamer chair while they eat last night’s dinner reheated, but to avoid a video-based conversation makes things weird. Who cares if you’re eating something? We all do it.

Standups—you need them

If there’s one event that gets the most bitching, it’s the team standup. The whole point is to have time to check in as a team—to see each other! It’s super important, but it’s also the first thing I see fall apart in remote teams. Some folks don’t want to wake up early. Others don’t want to do it during their lunch. There just never seems to be the right day and time that will work for everyone.

The best thing you can do for your team is to put your foot down and establish a regular, consistent time to check in as a team—and stick to it. Oh, and have an agenda! If you want to make standups interesting, then take a page from InVision CMO Brian Kardon’s playbook: Each team all-hands starts with a provocative question, and without fail a quick and a fun conversation ensues as team members enter the meeting. Sample questions:

• What was your first concert?
• What’s your favorite piece of art?
• Do you have a hidden talent?
• What’s your favorite book?

Also, don’t forget to stand

Because there aren’t any rooms to walk to for a meeting or a phone call (or frantic-jog to because you can’t find an open room), it’s easy to sit down for very long periods of time when working from home. After a while your body will hate you for this and it will begin to impact your mental and physical health. I try to stand as much as I can (I don’t have a standing desk) which means I stand during meetings, in-between meetings, etc. I also have an Apple Watch which tells me to get up and breathe (also important) on a regular basis. Whatever works for you, just make sure you’re moving and stretching throughout the day.

You recharge you

With the additional expenditure of using soft skills combined with the need for more patience, you need to make a point of recharging your own batteries. Find a buddy, a peer at work or someone in the community that you can talk to and unload. Putting yourself out there to take care of your team will take more energy. Who knows how long this is going to last so better to prepare for the marathon than assume this will be a sprint. And get plenty of sleep.

Remote takes a remote village

To those of you who are having to lead remotely for the first time—good luck. I’m hearing more stories of companies that are closing down their campus with not much more than a bare-bones HR/security plan. If you have questions, please feel free to reach out, and I’ll do what I can to find fitting answers. And if you have a design leader (director level or higher) who is not a member of the InVision Design Leadership Forum, please send me a message with an introduction.

Be well, stay well.