7 Tips for collaborating with a remote team

It’s no secret that more people are working remotely today than ever before. Employees appreciate the freedom and better work-life balance that comes with remote work. Businesses appreciate the savings on office rent and access to a wider talent pool.

If you’re a small business owner, hiring remote also gives you the option to vet talent by hiring them as freelancers first. Once you’re confident in their abilities, you can hire them on a full-time basis.

There’s only one problem: getting a remote team to work well together can be a challenge. It doesn’t matter whether you have a couple of freelancers or a 20-person remote team, you’ll want employees who can communicate and collaborate well together.

In this article, I’ll share tips I learned from my experience of managing a small remote team of creative workers. You’ll learn how to pick the right kind of employees, how to communicate with them, and how to maximize their productivity. While these tips are aimed at remote teams with 2-5 members, they’re equally applicable to larger teams or smaller groupings of freelancers.

1. Select “remote-ready” employees

   Remote work requires a certain set of skills not always found in office-going employees. For one, they have to endure long periods of social isolation as they work from home. They also have to motivate themselves to stick to a schedule even though there are no bosses or colleagues to watch over them. And while communication skills are important for any employee, limited face-to-face interactions means that remote workers have to be at least above average communicators.

   One way to build an effective remote team is to focus on hiring employees who display the above skills. Such “remote-ready” employees will find it easier to adjust to the communication-focused, socially isolated nature of remote work.

   Prioritize the following in your remote hiring process:

   • Non-traditional work experience: Pick employees with entrepreneurial, freelance or startup experience. This indicates that the person is a self-starter and won’t have the punctuality and motivation issues that often plague remote workers.
   • Strong communication skills: Focus on communication more than you normally would for regular hires. Make a list of communication channels you frequently use, then evaluate their communication clarity over those channels. For example, if you use videoconferencing extensively, hold at least one interview round over a video call.
   • Cultural-sensitivity: It’s not unusual to have remote teams with members from different countries and cultures. Pick people who have a proven record of working with diverse groups of people. Their diversity experience would make it easier for them to communicate in remote teams.

2. Create a digital “water cooler”

   So much of team building happens over casual conversations at the water cooler. One study even concluded that small talk improves cognitive abilities.

   In the absence of such a shared space – as in a remote office – your team’s conversations can often be limited to work-related topics. This might be good for productivity, but it’s not ideal for building a sense of team cohesion and camaraderie.

   Solve this problem by creating the digital equivalent of a water cooler. This should be a free, unmonitored (by you or a manager) space that all remote employees can access easily. It should encourage short, casual conversations and should serve as a distraction from work-focused chats.

   Here’s one way to create this digital water cooler:

   • Create a dedicated channel on Slack (or your favorite team communication tool) for casual conversations. Invite all remote employees to it.
   • Make this channel closed to direct managers. Your objective is to give people the freedom to say what they want without risk of penalty or censure by their bosses.
   • Encourage employees to ask each other questions outside of work. You can even automate this by using Slack bots such as Slido to ask casual questions every day that can serve as a prompt for conversations.
   • If you’re working with freelancers, invite them to this digital cooler as well. However, make sure that you limit their ability to access or edit files shared within this space. You don’t want to lose any internal company data to an outside contractor.

3. Invest in remote team building activities

   Just because you’re working remotely doesn’t mean that you can’t participate in activities together. In fact, a number of team building activities don’t require a shared physical space. A simple game of “virtual charades” can help break the ice with new team members.

   Here are a few things to consider when you invest in team building activities:

   • Online PC games are a great replacement for real-world games when it comes to team building. Pick games that encourage collaboration and teamwork over skill and luck. Team-based strategy games work particularly well in this context. Friday evening is a good time to host weekly gaming sessions. Keep these timed to a maximum of 3 hours lest they become an unproductive habit.
   • Pair people up randomly on a non work-related activity. Try to match up people from different backgrounds, seniority-level or expertise. The activity can be as simple as selecting a movie to watch over the team’s next retreat.
   • Designate one day where everyone keeps their webcams switched on while working. Use tools like Google Hangouts or Zoom to do this. A live video feed of each team member’s home office can help to create a sense of a shared space.

4. Automate messaging as much as possible

   When you’re sharing an office, reminding someone of an upcoming deadline is as simple as popping into the next cubicle.

   You don’t have such luxuries when working remotely. You have to send emails and messages for all reminders, alerts or notifications. Sometimes, you even end up setting reminders for yourself to remind others about a task.

   One antidote to this problem is to automate messaging as much as possible. Your project or task management software should be able to notify all concerned workers about deadlines, weekly meetings, etc.

   Here are a few things to keep in mind when you automate messaging:

   • Automate all recurring tasks (such as filling daily timesheets) as well as deadline notifications. Ideally, your project management software should also be able to send automated follow-ups and reminders for any unfinished tasks or missed deadlines.
   • Make sure that your automated messages don’t leave out any freelancers who don’t share your company email address or aren’t logged into your project management software.
   • Match the right channel with the urgency of the message. For example, you might send an early reminder about a deadline via an in-app notification in your project management tool. On the day of the deadline, you might follow-up with an automated reminder over email. If someone misses a deadline, you can send them an automated alert via a text message.

5. Meet face-to-face

   While video conferencing and casual chats are great, they are no substitute for face-to-face interactions. One study published in Harvard Business Review even concluded that 35% of the variation in a team’s performance can be ascribed to the number of face-to-face encounters they have.

   You don’t have to meet weekly or even monthly, but a couple of drawn out face-to-face interactions per year can help. Usually, you’d want to do this over a semi-annual team retreat where everyone has plenty of time to get to know one another.

   Here are a few pointers for hosting a team retreat:

   • Retreat location: Invite suggestions from team members to decide on a retreat location. Once you have all the suggestions, ask everyone to score each location on its desirability (example: “Colorado = 5,” “Florida = 8,” etc.). The destination with the highest score would be your team retreat location.
   • Retreat manager: Assign a “retreat manager” who will be responsible for coordinating the retreat with other team members. This can be a great opportunity to give some responsibilities to a junior member and build their leadership skills.
   • Decide on a budget: Your biggest expenses will be airfare and hotels. For a foreign destination, estimate at least $2,000 per person for a week-long retreat. You can cut this significantly by picking a domestic destination. Also decide whether you’ll be covering food and local transport costs as well. If yes, set aside at least $100/person/day for food and transport.
   • Retreat participants: For best results, your retreat should include everyone who works on the team, regardless of whether they work remotely or from your office.

   Apart from team retreats, you can also encourage team members who live in the same city to meetup. Don’t hesitate to break the ice by scheduling informal online chat sessions between them first. You’ll find that more face-to-face time will result in stronger teams.

6. Invest in better collaboration tools

   One of the biggest challenges in working remotely is imitating the back and forth of real-life collaboration. This is particularly true for creative work where any lag in conversations can impact the exchange of ideas.

   The only solution to this problem is to invest in better collaboration tools. Ideally, you should have three separate tools:

   • Domain-specific tools: These are tools to facilitate collaboration over a specific activity or domain, such as wireframing,  coding, or drafting. Google Docs (writing), Balsamiq (UI prototyping), Onshape (CAD) are examples of such tools. If you’re a non-technical company, you might not need this type of tool. Technical companies, on the other hand, might use different domain-specific tools for different departments.
   • Project management (PM) tools: These are tools that help everyone keep track of any project and all the tasks associated with it. Your team members will use it to share important documents, log time, and manage work. If you work with clients, pick a tool that also offers a client-facing portal as well. You can also choose between a domain-agnostic or domain-specific PM tool. The former (such as Basecamp) will work well for any business.  The latter (such as Newforma for architects) will have features specific to a single industry or vertical.
   • Communication tools: Tools to help your team communicate better. These can be in the form of chat (such as Slack) or video conferencing (such as Google Hangouts). Instead of picking multiple communication tools, understand your team’s habits and pick a tool that works well with them. For instance, if your team prefers short, casual chats, pick Slack. If it prefers video calls, prioritize Google Hangouts.

   You’ll use project management and communication tools to keep everyone on the same page. People from a particular department (such as design) will turn to domain-specific tools to collaborate on specific activities.

7. Be a more proactive manager

   The best tools in the world can’t overcome poor managerial practices. You’ll find this to be particularly true when you’re working with a remote team. Minor managerial lapses can blow up into major issues in a remote environment.

   The only solution is to be proactive. You have to constantly take steps to get the best out of your team. Here are a few things you can do:

   • Check-in frequently: In one survey, 46% of remote workers said that effective managers checked-in frequently and at regular intervals. Create a regular schedule for asking team members about a task or even about non-work topics.
   • Understand your team members: Try to understand how each one of your team members works. What kind of schedule do they like to follow? Do they work best alone or in a group? Build a work structure around each member’s likes and dislikes.
   • Offer communication training: Most problems in remote work can often be traced to poor communication. Improve this vital skill by holding training sessions and developing best practices for communication.
   • Keep everyone on the same page: Ensure that everyone on the team has access to the same information. Proactively ask people if they have the same data and insight as the rest of the team. Create a central repository of all documents associated with a project to help information exchange.