The “gig economy” is on the rise and it appears to be all the rage. Are you in on it? Or on the outside looking in? Could your business benefit from having a remote workforce? Perhaps even having global employees?

Small and medium sized businesses could reap huge benefits from remote teams — but there are also risks. In this article, we’ll share advice from CEOs of remote workforces that they wish they’d known earlier.

Telecommuting desk
Image courtesy of Mike McCune under a Creative Commons license.

Types of Remote Teams

While remote teams are all similar in that the staff is not located in a centralized location (such as a shared office), that is the extent of the similarity. The individual employees are left to decide on the work situation that best fits their needs.

If these positions are freelance or contract jobs, they are short-term positions where the employee moves on after project completion. However, there are full-time positions that are, for all intents and purposes, identical to your typical day job: you get a salary, you put in a set amount of time each week (typically forty hours per week), and you get some type of benefits package. There are also jobs with flexible arrangements that allow you to work remotely for some part of the week.

There is one major difference between remote work and a traditional job: rather than clocking in or out of an office, you can work from wherever you would like, as long as you have access to a sufficiently fast internet connection.

Working From Home

Generally speaking, most people think of working from home whenever remote work or telecommuting comes up. However, working remotely from home, which is exactly what it sounds like, is not the only option available.

Working Outside the Home (But Not in Corporate Offices)

For those who cannot work from home (primarily due to the distractions present — dishes, laundry, answering the phone, and so on), there is the option of working outside the home, but at places of the employee’s choosing: libraries or the ever-popular cafes.

However, there is a new option that is gaining in popularity for remote works: co-working spaces.

What are Co-working Spaces?

Co-working spaces are communal offices where people can “rent” the space they need for the time they need. These shared offices offer the basics, such as desks, high-speed internet, and private spaces for things like meetings and phone calls. Some premium offerings even come with things like yoga classes, kombucha and beer on tap, and so on.

Co-working space
Co-working spaces provide a shared working environment for remote workers.
Image courtesy of Impact Hub under a Creative Commons license.

“But wait! Isn’t the point of remote working to avoid going into the office?” you ask.

Well, yes and no. Co-working spaces are a good option for those who cannot work from home, yet do not feel comfortable squatting on a table at their local cafe for forty hours (or more).

But, more importantly, remote work allows employees to seek work with companies that are not located in their city of residence — the co-working space is simply an available tool that the employee can take advantage of if desired.

The Upsides and Downsides of Managing Remote Teams

Regardless of the working arrangement chosen by employees, what are the upsides and downsides to managing a remote team? In the following sections, we will cover some of the pros and cons associated with managing a remote team and what current remote team managers think about the issues at hand.


  • You aren’t limited by geography when seeking a talented workforce.

Many managers say that it can be difficult to hire locally and, if you require your employees to show up physically, you are limiting yourself to hiring from a small pool of people (typically those who live within driving distance, though the higher the salaries you offer, the further your reach).

This problem is mitigated by a remote workforce — as long as the person has a computer and a suitable internet connection, they have everything they need to join your company. This increases the likelihood that you’ll find a good fit for the role at hand.

Looking for remote talent? Popular sites include: Remote.coRemoteOKRemotiveNo Desk, and AngelList.

  • You’ll spend less on costs related to office spaces.

Office space is not cheap (and it is especially not cheap if you are in high-cost-of-living areas like San Francisco, Seattle, or New York City).

Rent for office space, moreover, is not the only expense you’ll incur. You’ll need to furnish your spaces, maintain them, and stock them with everything your employees need (including, but not limited to, office supplies, snacks, and so on).

All of this adds up, but when you have a remote team, some of these expenses go away. You will still have to provide your employees with equipment, but you do not have to pay office rent or for furnishings.

  • Your employees are more productive due to the better work-life balance.

There’s a lot of talk about work-life balance, and most of it has revolved around making things work around the typical workweek: Monday through Friday from 9 am to 5 pm. However, there are a lot of problems with this model including:

  • Difficulties when scheduling appointments: doctor’s visits, trips to the bank, and so on all have to fall during a typical workday, meaning missed time in the office
  • The juggling that families have to do: those with young children might find it difficult to juggle between sick days and work
  • Not accounting for individual preferences: some people are early birds, and some people are night owls — remote work allows for some flexibility in work times since people are not expecting to all be working at the same time in the same place

Remote work, especially the positions that offer time flexibility as well, makes it easier for employees to juggle things as they see fit. First, there is the nonexistent (or minimal) commute to the workspace. Then, the employee’s time can be used as appropriate — people certainly need to show up to meetings they have committed to, but maybe they work late one day and start early on another so that they can be at their children’s holiday concert.

By reducing the stress levels of your employees, you will have a more productive, happier workforce.

  • There are digital analogs to most in-person techniques for office and team management.

Interested in the Agile methodology? There are tools for facilitating Scrum-based team stand-ups (or meetings) with remote teams.

Want to set up recurring conferences? There are communication and collaboration tools that make doing so easy. Some are free (Google Hangouts, Skype), while others are paid, premium products (Zoom).


  • Interviewing and Hiring Can Be Difficult

We mentioned in the upsides section that, with a remote workforce, the pool from which you can hire grows exponentially. However, you still have to hire the right person, and it can be challenging to do so from a distance.

Today’s technology allows you to collect and review resumes and interview people, regardless of where they’re located, but you are missing information that you would otherwise get meeting someone in person (such as nonverbal cues).

There are, however, ways of interviewing designed to pick up on cues you may find helpful.

Matt Mullenweg, the CEO of Automattic, the remote company behind the WordPress content management system, recommends setting your interviewees up with a project to work on. This task would typically take a couple of hours, and in addition to giving you insight into the candidate’s job-related knowledge, you can gain insight into their communication skills, ability to work independently, and so on.

Early on, Mullenweg drove a more traditional interview process, a choice he believes led to a higher staff turnover.

automatic screenshot
Automattic changed its hiring process and reduced staff turnover.
  • It can be difficult to build a solid team/workplace culture.

There are a lot of perks to having a remote workforce, but that doesn’t mean that there aren’t positives to having a shared office where everyone goes to work. Water cooler chats are a major pick-me-up for employees. With a remote workforce, there are only digital (and somewhat inferior) alternatives. People can certainly congregate on a channel designed for off-topic chat, but it is not quite the same as an in-person conversation.

To compensate, many remote companies take advantage of annual or biannual team retreats or off-sites, where everyone in the company gathers together for a week or so. These are expensive, but it offers employees a chance to meet others in person, engage in team building opportunities, and so on.

buffer team
The Buffer team blogs regularly about building company culture within a remote team
  • It can be difficult to communicate effectively.

Very few people have never posted something on the internet that was then misinterpreted or misconstrued by something else. When you have a remote team that uses written communication with increased regularity, miscommunication, dropped communication, and so on are problems that can throw major wrenches into your projects and daily productivity.

Furthermore, there are some remote jobs that ask employees to be online and available during certain time periods (namely technical support jobs and the like), but many employees assume that their schedules are somewhat flexible. As such, remote teams can be less responsive — you may be able to get someone on the phone right away, or you might be dialing helplessly as they sit waiting at the doctor’s office.

Finally, it can be difficult to set up meetings simply. If your team has multiple people spread out over the world, finding a common meeting time that works for everyone can be difficult. Your Australian contact might be available at 2 am, but they certainly won’t appreciate having to get out of bed every Thursday to go to a team catch-up meeting.

  • Not everyone is cut out for remote work.

Remote work removes the in-office distractions of chatty coworkers, last-minute meetings, and so on, but being out of the office doesn’t eliminate distractions — it merely replaces them.

If your employees are working from home, can they resist the siren call of the dishwasher or the dryer beeping with a load of freshly-dried clothing? If they are in a coffee shop, can they resist packing up and taking a leisurely stroll through downtown?

While we all want a workforce capable of working independently no matter what, some people do need the structure of a workplace to keep them on task. It can be difficult to screen for these types of employees since the siren call of working remotely can be so powerful.

  • Work-life balance can be a myth for some.

When working remotely, it can be hard for some to separate their work lives from their personal lives (especially if they work from home) — in some cases, the two can merge so that the person is always on and working around-the-clock. In the short run, this is beneficial to the company in terms of output and productivity, but in the medium- and long-run, this will quickly lead to employee burnout.

As a manager, it is important that you set up a (remote) company culture that discourages the always on, highly responsive mentality some people may have. It’s not enough that people don’t respond around the clock — it’s important that people don’t expect this as well. Managing a remote workforce is complicated, and this is one of the major challenges contributing to this difficulty.

Advice from the CEOs: Managing a Remote Team

While there are definitely similarities between managing a remote team and managing a team in-person, there are some differences that you will need to take some time to reflect on and change your management practices.

Clarify Expectations

In some ways, the sources of stress for your employees can seem small:

My heart races as that familiar bubble pops up on my screen. My supervisor is typing for what seems like forever. In reality, it’s only a few seconds, but that’s still enough time for me to fall into a full-on worry spiral: Did I make a mistake? Is she mad at me? Finally, the text message appears: “Thank you.”

Conversely, the communication challenges we wrote about above can result in bigger issues. For example, if communication between you and your employees drop, the uncertainty this causes may result in lowered employee morale (regardless of whether there is any truth behind the assumptions made by the employee).

Kari DePhillips, the owner of the Content Factory, realized many of her messages to remote employees were too negative. To improve morale, she places an emphasis on positive feedback.

The solution is simple in concept, according to Mark Mortensen, an associate professor of Organizational Behavior at INSEAD:

“As the manager, you need to set clear, deliberate expectations in advance and establish ground rules for how interactions will take place.”

Executing this, however, can be difficult. The specifics will vary based on your particular management style, as well as the preferences of your employee, but the key is to make sure that things are clear and predictable. Above all, it is the uncertainty (from the perspective of the employee) that is problematic.

Acknowledge Contributions

It can be hard to “see” the contributions made by remote employees, but it is important that these employees are recognized the same way traditional employees are.

In general, employees find that lack of recognition is demoralizing, and remote workers are no different. However, there is a lot to consider when providing recognition, so you will want to make sure that you are going about this the right way.

Handle Issues Immediately

As the old saying goes, “Out of sight, out of mind,” and remote work can hide a lot of issues that would otherwise be in your face in a traditional office. To keep things from festering and causing even bigger problems down the line, acknowledge and handle issues as they pop up.

Denis Duvachelle, the CEO of Twoodo, describes how team members had several arguments due to miscommunication. He introduced regular scrum meetings to keep geographically distributed team members on the same page.

Unite the Team with a Shared Vision

Building a strong team culture among employees scattered across the world can be hard. Time zones and little face to face communication can harm morale.

Arvind Sarin, the CEO of Copper Mobile, noticed animosity brewing between teams in different time zone. Sarin diffused the tension by sharing business goals, uniting remote team members behind a shared goal.

What’s the Bottom Line on Remote Teams?

There are a lot of pros and cons to having a remote team, but managing such a team requires slight tweaks to the management toolkit you have today. Many things remain the same, but there are natural differences between the two working style that brings up new challenges.