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Professional Development

Calendly shares tips to help you and your team work together effectively in a remote environment

So much of the way businesses think about teamwork is rooted in the tradition of in-person co-working. Just think about the vocabulary that gets used.

You sit down with someone and have a “head to head.” Casual office chats are referred to as “water cooler conversations.” When people talk about working out a deal, they often talk about “being in the room together.”

This vocabulary is so commonplace that team leaders often come to believe that remote work automatically means less collaboration. Working together is different when you have to meet through a computer screen, but you can accomplish just as much remotely as you in person.

The importance of checking in

Most teams hold group discussions from time to time, reflecting on what’s been working and what hasn’t. From there, teams can make more informed decisions on what direction to take next.

For some, it's a formal process that happens weekly, biweekly or monthly. Others check in on a more informal basis, sending a quick email or stopping by one another’s desks to see how things are going.

With the right tools and the right strategy, either of these approaches can work for remote teams. The most important thing is to keep everyone in the team involved and make sure all voices are heard.

How to set up a collaborative remote meeting

When you’re learning how to run a remote team, one of your biggest tasks is developing a strategy for virtual meetings. Here's a basic guide that can be adapted to meet the needs of your team.

Step 1: Create a space where all voices are welcome

According to a survey by social media marketing company Buffer, 19% of remote workers say that loneliness is their biggest challenge. It’s hard to feel connected when you’re physically distanced from your team and every interaction you have with a company feels like a chat with the cheapest voice over actor in the world. Being human is important. Humans don't speak with tag lines or jargon every other word.

While it may be easier now that whole offices are going remote, it’s still a challenge to feel like you’re all working together. The first step is to cultivate a team environment where everyone is invited to share their thoughts and all feedback is welcome.

This can be a tough goal to accomplish, especially if your team hasn’t been actively building a pro-feedback culture since before you went remote. If you have, congratulations—you’ll have a smoother road ahead. But if you haven’t, don’t worry! You can still position collaboration as a team value. You just have to be explicit about it.

Every time you have a meeting, ask for feedback and opinions. Some people are understandably shy about sharing feedback, having been on teams where it wasn’t so welcome. Be clear that all constructive thoughts and observations are okay.

When someone shares an insight or suggestion, thank them. Let them see you write it down. Invite them to message you privately if they don’t feel comfortable sharing with the group.

Pro Tip: If your team seems to shy away from constructive feedback, model it by commenting on your own actions: “I noticed that I didn’t stay in touch with the client as much as I should have on that project. I’m making a note to schedule weekly check-ins for this next time around.”

Step 2: Plan the logistics in advance

Virtual meetings need more planning and logistical preparation than in-person meetings. You can’t just grab a whiteboard, head for the nearest conference room and “open the floor.” You need a virtual space to have the meeting and a time that’s good for everyone. In most cases, you also need a structured agenda.

Your first step is to set up a video call. Try to use a tool that allows you to see multiple video feeds on-screen at once. Discussions tend to be more productive when you can see people’s faces, so encourage everyone to have their cameras on.

Next, create a plan for the meeting. Don’t worry about planning it out to the minute. You’ll want to leave room for discussions to bloom and evolve, but it’s helpful to have an overall structure with topics you want to cover. A good basic format is:

  • What went well

  • What didn’t go as well

  • What challenges people faced

  • What changes the team will make going forward

Make sure you have a way to write down the ideas you collect. Ideally, this will happen on-screen in a way that allows people to contribute. The easiest way to make this happen is with the annotation tools included in many videoconferencing platforms. You can take notes yourself as the meeting host or allow everyone to mark up your digital whiteboard

Pro Tip: Scheduling virtual meetings can get chaotic if you try to plan them by emailing back and forth. Streamline your planning process with Calendly’s team scheduling function. You can view everyone’s availability on a single page and choose a time that you know works for the whole team.

Step 3: Review what people have been working on

When your team is remote, it’s harder for everyone to stay in the loop about what’s going on with the broader team. Start your meeting with updates on what the plan had been for the period you're reviewing, what was accomplished and anything important that happened along the way.

If possible, make it a collaborative effort. There are several ways of doing this. One is to have each team member say what they have accomplished and/or been working on. Alternatively, you can do it “popcorn style,” everyone calling out—or writing down—one significant accomplishment or roadblock they remember.

If there’s a particular problem the team has been working to solve, make sure you review that area and check in during your next meeting to see what progress team members have made.

Pro Tip: If you’re doing a popcorn-style or round-robin discussion, keep in mind that all videoconferencing tools can have slight time delays. Some platforms have incorporated features that let you signal when you want to talk. Encourage team members to these features so people aren’t talking over each other.

Step 4: Find the “why” and the “so what”

Once everyone is on the same page, it’s time to dive deeply into lessons learned and areas for further discussion. This is where you'll get the most return for your work on cultivating respectful dialogue.

When someone brings up a problem or challenge, don’t play the blame game. Instead, dive deeply into why the problem happened and why it matters that you solve it. For example, the fact that a team member missed a deadline might not merit a discussion on its own, but if there’s a pattern of missed deadlines, you need to figure out what’s going on.

There’s a helpful exercise called “the five whys” that can help you get to the root of recurring issues. You ask why a mistake or problem occurred, then look for the reason for that reason. Usually, you’ll find the root cause within five “whys.”

An overall structure helps keep these discussions on track. Remember those four categories mentioned in Step Two? Write them down on your digital whiteboard. You don't have to touch on changes to make yet—that comes in during the next step.

Pro Tip: Integrate as many of your tools as possible. By connecting any work management, videoconferencing and scheduling tools you may be using, you’ll have an easier time accessing the information you need and keeping track of the changes you want to implement.

Step 5: Create your action plan

If you’ve focused on the “so what” throughout your discussion, planning your next steps will be a breeze. Start building your action plan with another round-robin or popcorn discussion. Invite people to weigh in with the answers to two questions:

  1. What have you learned?

  2. What should we change?

Develop a list of action items, then get people to take the lead on each one. Make sure each assignee knows what success looks like—will there be X% fewer missed deadlines? A specific turnaround for a particular type of task?

Pro Tip: Keep your goals achievable and relatively small-scale, at least at first. Communication tends to take longer when a team is remote, and you want people to feel motivated and confident rather than overwhelmed. If they meet goals this first time around, they’ll be ready for the next challenge.

Step 6: Get feedback from the meeting

Remember that point about modeling effective feedback patterns? Here’s another moment to practice it.

You want your team to feel comfortable giving you feedback, so ask them how they felt about the discussion. Did they feel like it had a good flow? Was everyone comfortable sharing responses? Make note of their feedback and then make necessary changes so team members can see you’re taking their insights seriously.

Pro Tip: End the meeting on a positive note by asking everyone to share their appreciation for each other. This is a good step to do in Gallery view so everyone can see each other's reactions.

A Final Word

Learning how to run a remote team effectively isn’t a quick process, but it is possible, especially with an enthusiastic, responsive team. The more they participate, the smoother things will go, so keep encouraging people to step up. Ask them for suggestions and tweak your process until it all goes smoothly.

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