Beating The Six Main Challenges Of Managing A Remote Team

Far from being a temporary pandemic annoyance, remote work is rapidly being embraced and ramped up by organizations that recognize its undeniable benefits.

Work-life balance, boosted recruitment and retention, lower operating costs. Remote work offers tangible advantages to companies and their employees, and is rapidly becoming the status quo.

But that doesn’t mean it’s without its challenges and hurdles. After all, only 6% of Americans did it full-time before 2020, and it took a global pandemic to push remote work into the mainstream.

Now that businesses are embracing it wholesale, overcoming the core challenges of remote work and managing a remote team will separate the good from the great.

Let’s take a look.

1. Where is everyone?

The first challenge is the most obvious. How can you manage a team who aren’t in the same room as you, who you can’t just grab a chair and sit next to, and who might be in a different city, country or continent?

Management thrives on communication, connection and conversation - all seemingly impossible in a remote world.

Remote work frees your business of the necessity of investing in office space, but it therefore makes cloud-based connection tools unavoidable as a counterweight.

There’s no getting around it: emails won’t do. Long back-and-forth chains will clutter, confuse and complicate communication, preventing your remote team from getting on the same page.

Consider a system like Slack or Teams that enables instant, back-and-forth digital conversation, as well as video conferencing where needed.

2. Time zones

Does your organization have global, multi-continental ambitions? If so, you probably require presence across time zones. Even if you’re only spread across the United States, you might still face the problem of a Boston team getting to work, and knocking off for the day, 3 hours before your Seattle workers.

Consistently setting a 7 pm meeting for an east-coast team, or asking your west-coasters to start work at 6 am, is a great way to annoy your colleagues and erode the work-life balance benefits of remote work.

Consider setting a Venn diagram ‘overlap’ period around the middle of the day for scheduling meetings, calls and catch-ups in regular work hours for everyone, regardless of where they’re based.

To take this further, think about how to make flexible work possible: where out-of-hours calls are unavoidable, give workers the flexibility to take an hour two off in lieu. 

Or engineer meetings which people can join asynchronously - perhaps by viewing recordings, notes or action points when they’re next back online.

Remote work provides a golden opportunity to be inventive and ditch superfluous meetings, forcing you to consciously plan communication times that connect and empower your colleagues without making time differences a hindrance.

3. Culture

Back in 2021, I worked for a software company which refused to permit remote work for a minute longer than was necessary.

I heard members of the business discuss how it was ‘time for people to return’, how the business culture could only be built with physical interaction in a central office, that managing a team was impossible without reading the body language and subconscious cues of a person in the same room.

“I’ve got a member of my team who has expressed that they prefer working from home,” one member of the team said with a raised hand. “I’m concerned that forcing people back into the office will trigger her, and other people, to leave the business.”

“Let them leave,” was the shrugged reply.

And they did. And the culture of the business, with this gung-ho approach to talent retention, was one of the worst I’ve ever experienced, remote or not. Checking Glassdoor right now, it appears to be the same a year on.

What does this story tell us? Many businesses assume remote work is antithetical to a real company culture and only by being in the same room can we get the spontaneous, concerted collaboration which makes a company tick.

If you’re not careful, there might be some truth to this: let remote workers drift apart, with too little communication and support, and they may feel unmotivated and disconnected from the corporate mission.

But make your culture one of trust, autonomy and intentional communication, powered by flexible working from anywhere, and it will beat an artificial and forced ‘get to the office’ culture drive every single time.

This is closely connected to Challenge #1 and its solution: give your remote team the digital framework to talk to one another, about work and non-work, and a culture will blossom of its own accord. 

To do this, weave the work-life benefits of remote work into your culture and make it part and parcel: encourage colleagues to talk about personal interests and give them virtual rooms and spaces to do so. Slack rooms about football, gardening, cooking or the latest TV shows are all good examples.

And to keep your teams aware of what’s going on and continuously buying into the company direction of travel; try a monthly or fortnightly all-hands virtual meeting with updates from different departments.

4. Switching off

Working from home can pose another challenge to remote teams by stripping away the mental dividing point of the commute. So-called ‘boundary theory’ holds that the act of traveling to and from work allows a psychological shift between work and life roles. Work is pinned to a clear physical area you can enter and leave, and so is home - with your car, train or bike the mental mediator between the two.

Take away the commute, and people find it difficult to move between these work and home ‘zones’. A Microsoft Survey found out-of-hours communication up by 69% during pandemic remote working, with people working longer hours than they otherwise would in an office and feeling more fatigued and burnt out as a result.

How do we fix this? Apple TV’s new Severance presents a dystopian future where workers ‘sever’ their consciousnesses into private and work memory streams, with ‘outies’ unable to remember their ‘innies’’office hours and vice versa. It’s a great show too, watch it.

Thankfully, we probably don’t need anything quite as extreme to bring balance to remote work. In early 2022, Belgium became the latest country to enact ‘right to disconnect’ laws, allowing workers to ignore out-of-hours work correspondence without fear of reprisal. Consider implementing an informal version of this for your remote teams to allow colleagues to switch off at clearly demarcated hours. Tools like Slack allow notifications to be paused at bespoke time intervals, for instance.

To take this even further, encourage your remote team to block out their calendar for private activities like the school run, gym or shopping.

5. Task management

Without constant in-office conversation, priority-setting and desk huddles, remote workers can struggle to know which tasks to prioritize from their home offices.

Alongside communication tools like Slack, make sure you provide your remote teams with task management tools like Asana, Monday or Trello, and any additional resources like monitors, laptops or office equipment they might need to be comfortable and consistently productive.

Weekly or bi-weekly 1-2-1s can help coalesce your team around priority tasks and ensure nothing slips.

6. My loneliness is killing me

Are some members of your remote team suffering from low morale? Without proper care, remote work can be an atomizing and lonely existence devoid of office chat, sudden kitchen snacks and water cooler in-jokes.

At the same time, your colleagues should feel enough of a connection to you as a human being - not pixels on a screen - that they feel comfortable enough to discuss any problems, work or personal, which will inevitably arise.

Ensure cameras are always on for video calls to build familiarity, and encourage colleagues to share non-work information if they feel comfortable. Conversely some personality types may not appreciate small talk, so watch out for that too!

Above all, give staff the option to meet and work in-person occasionally if they wish to do so. Set aside some budget for temporary remote office hire if you have groups of employees in physical proximity, and consider annual or quarterly (optional) meet-ups to get teams together.

Remote work can be empowering, mood-boosting and environmentally friendly but, in certain circumstances, tempering it with the odd physical meet-up might be no bad thing.