How to Manage a Kick-Ass Virtual Team

One of my favorite questions to get from new people, when they learn about my company, is “where are you based?”

It’s my favorite because there’s really no short answer to it. “The company is based in Boston,” I usually answer. “But our team is everywhere.”

What do I mean by everywhere?

I mean Boston, New York, Boulder, Toronto, Madrid, and Nicaragua.

Our team is a microcosm of our global community — and that’s exactly how we like it.

Of course, there are huge challenges when your team is virtual. I used to joke about my dream of a big, gorgeous office. It’d be a sort of National Geographic meets Pinterest, with big open windows, brick walls, wood floors, and pictures everywhere from around the world. It’d have hanging paper lanterns, and a cute café for employees with couches covered in pillows with global textiles. Every Monday, we’d have a manicurist come into the office for fun, and on Fridays, we’d have open wine and cupcakes for everyone.

When your team is in the same place, you can build culture. You get to know each other on a level that you simply can’t do virtually. In my opinion, face-to-face interactions are absolutely essential to relationship building. And often, having an in-person meeting to hash something out can be so much faster than typing back and forth over email. Not to mention that there’s just something about Manicure Mondays that sounds so tempting.

But in today’s world, we simply have no need for that dream office. By enabling our team members to live anywhere, we are able to pull from a variety of insights and perspectives, while also giving our staff the ability to travel and work flexibly (which is what we’re all about anyway, isn’t it?). It also saves us a significant penny on costs, which we can use for other important elements of our business.

That being said, as an entrepreneur-turned-manager, it means I have to work extra hard to build team culture, maximize the efficiency of our interactions, and enhance team dynamics. Because we don’t have the luxury of seeing each other everyday.

Here’s what I’ve learned:

Use your tools

My headset looks huge, but it does the job!

Lucky for us, now is by far the easiest time to manage a virtual team. There are so many tools available to us that even the most traditional corporations are able to offer their employees the opportunity to work from home every once in a while.

Save your inbox by getting a communication tool like Slack. Not only has it drastically cut down the number of emails I receive, but it allows your team to have conversations and weigh in on different topics. You can also privately message people if you have a quick question and don’t need the rest of the group to know. Or you can create channels for various topics. Our team is partial to the #random channel, where we mainly spend our time fawning over heartwarming articles about Justin Trudeau.

Make sure all of your documents are on a cloud like Google Drive. That way you can create agendas that everyone can edit quickly for your meetings, have multiple people work off of one spreadsheet, and keep tabs on each other without having to check in virtually.

When possible, opt for a Google Hangout over an email thread. Sometimes just getting on a call and talking something over (preferably on video, but audio if necessary) can take much less time than typing multiple emails back and forth. It also is much cheaper if you have international team members than calling them on the phone. Plus, you gain the benefit of face time, which is essential in virtual teams. Make sure to have clear start and end times for your meetings, and create an agenda if necessary to keep yourselves on task and operating as efficiently as possible.

To make your calls the best they can be, get a good headset so you can hear each other well. I personally use the Logitech ClearChat USB headset, which has an excellent microphone. I’ve definitely used it in coffee shops and my team hasn’t known the difference (except that maybe I was whispering).

For my video calls, I purchased the Logitech HD Webcam C310 for about $30 on Amazon (I figured I’d keep going with Logitech since my headphones were so great). I have had multiple meetings where people have commented on the quality of my video. Just make sure you’re looking good — because the camera will pick up everything J

Culture, culture, culture

One of the hardest things to build in a virtual environment is a team culture. We lose so much information when we’re not talking in person — sometimes we don’t know when someone is making a joke, or being sarcastic, because we can’t read their body cues or don’t know them that well. That’s why it’s absolutely essential to make creating a team culture an absolute priority.

As I mentioned in my recent article about making the jump from entrepreneur to manager, helping your team understand the “why” of your business is not only important, it’s necessary. When you’re working together on a virtual level, however, it’s even more essential. Make sure to take time to sit down with them on Google Hangouts and talk about where you come from and why you do what you do. Encourage them to co-create important company documents with you.

Take the time to learn about your team members’ lives. Since no one has a cubicle, we don’t get to see how we decorate our spaces, or what pictures we have on our desks. Instead, we talk to each other. Take time before every meeting — even your most efficient ones — to ask people how they’re doing. Share information about yourself and build camaraderie. This indicates to your team that it’s ok for them to get to know each other and not to cut to the business all the time. I’ve been known to share some pretty weird stories before our meetings start. In many ways, it invites my team members into my world, and shows them that I want to know them, too.

Meet up in person

Taking in some sunshine with some early team members before WITS ’16 in Irvine, California

If you’ve got a corporate credit card, you can often get great cash back deals on your purchases if you shop through the card website. I’ve used necessary purchases like office supplies and marketing materials to rack up points on my card, which then I’ll use to fly my team to the Women in Travel Summit a few days early for some retreat activities. We also tend to take our business trips in pairs, often because a second opinion during a site visit or another set of notes during a conference is useful to us, but it doesn’t hurt that we get some quality time together as well.

As often as you can, prioritize these face-to-face meetings. Set up an annual retreat where your team is physically together in one place. Pick a new location each time so it’s more or less convenient for alternating members of your team. Show them that you value creating that team dynamic.

Give perks

One of my proudest moments was in Wanderful’s early days, when I sent $10 to each member of my team on PayPal. I instructed them to go to the store before our next meeting and to use that money to purchase their beverage of choice, and we would enjoy it together virtually. It just cost me about $50 at the time but that gesture made all the difference in the world, and made our meeting so much fun. When you can’t bring in breakfast for the team or have happy hour after work, find other ways to mimic the experience. Your team will thank you for it.

Celebrate your team’s successes

It’s easy to fall into the trap of getting things done and immediately checking out when your interactions are almost entirely virtual. Everything moves much more quickly and it seems there isn’t time to slow down and reflect. This is why reflection and recognition is so much more valuable in a virtual environment.

Make sure you’re taking a moment at every team meeting to acknowledge work that your team members have done well, or celebrate them in an email. I have started to use the amazing /praise/ shortcode in Slack as it makes a public announcement to a team member who has achieved something.

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Though I do sometimes still fantasize about that big open office with every amenity my heart desires, today I am grateful for having a virtual team. It allows us to be everywhere our community is, and also gives our team members a flexibility that they couldn’t enjoy anywhere else. I love that we are able to work wherever and whenever we want, and still get everything done that a traditional team does. Is it more difficult? Sure, in many ways. But can it be more rewarding?


Which of you has a virtual team? What do find are the biggest challenges and the biggest strengths? Interested in turning this into a conversation and hearing your thoughts!