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Remote Working 101: The Ultimate Guide to Managing Remote Teams

Software isn’t just eating the world, it has also helped break down the four walls of the traditional office. We've collected valuable remote working insights, experiences, and advice for small businesses who want to travel down the micro-multinational road.

Remote Working 101 The Ultimate Guide to Managing Remote Teams

In just the past decade or so, telecommuting has increased by 80%, giving more and more companies access to a literally global talent pool. Companies can now hire top talent wherever they might be, and employers can even choose to hire talents in areas where salary expectations are more manageable.

Need more proof? Check out these numbers from Global Workplace Analytics as well as our newest infographic on remote working (feel free to share the infographic on your blog):

  • American Express reported that remote workers produced 43% more than their office based counterparts.
  • Best Buy, British Telecom, and Dow Chemical reported that teleworkers are 35-40% more productive.
  • 46% of companies that allow telework say it has reduced attrition.

WORK[etc] the company is a big fan of remote working. In fact, our team is spread across four continents all over the globe. Not only does this setup help the company, it also benefits our customers — especially when it comes to support. Since our support team is global (just like our user base), we’re better equipped to provide support to our users 24 hours a day.

But for all the benefits of running a distributed team, it can also be incredibly difficult and frustrating. Not every business that tries to implement remote work policies will find immediate success. In his article, “Why Remote Work Thrives in Some Companies and Fails in Others“, Sean Graber claims that it all boils down to the three Cs — Communication, Coordination, and Culture.

WORK[etc] isn’t really much different; we’ve certainly had our fair share of wins and losses in the remote working environment. Recently, we asked seven business managers to share their insights and advice for working with remote teams. Here are their answers to our questions.

Q: How do you efficiently hire remote workers that best fit your business? What are the most important qualities to look for in a candidate?

01 Finding Remote Workers that Fit your Business

We have a very stringent interview process at TeamSnap to make sure our candidates not only have the skills they need for the job but also that they are a good cultural fit for the company, which includes being self motivated, able to work independently, and goal driven, all extremely important for someone who won’t be working side by side with a supervisor everyday.

Generally, every candidate interviews with the person who would be their supervisor and with other people in their department, and then also with our co-founders—our CEO and our Chief Product Officer, who also doubles as our “minister of culture.” They act as our litmus test to gauge a person’s cultural fit, and they talk with the supervisor about how this person will do in a remote working environment.

If there are concerns that the person won’t be able to work independently or require too much supervision, that person isn’t a good fit for us.

This process has generally worked really well for us; there have only been a couple of situations where someone was hired and then it turned out working remotely wasn’t for them. In those situations, it’s usually a mutual decision where both the employee and the company felt it just wasn’t the best fit.

Ken McDonald
Chief Growth Officer, TeamSnap

How to hire remote workers:

  • Get creative with Job Details for breakthrough. Use unexpected or surprising words, but make sure you explain the headline within the body of the job description.
  • Don’t use inflated job descriptions to describe the role. Keep it simple. Keep it task-focused and explain how those tasks relate to the outcome this role needs to deliver. Don’t be afraid to stand out from the crowd by being personable and telling the story behind the role.
  • Offer above industry rates to attract qualified candidates and fast-rising stars. Don’t be afraid to state a dollar figure in the advert.
  • Promote the benefits that make working for your micro-multinational more desirable than an equivalent role at a big-name company.
  • Set a simple task along with how-to-apply to quickly identify people that are truly interested in the role.
  • Take advantage of tools like ZipRecruiter to efficiently manage and screen applicants.

Read more on how WORK[etc] recruits its remote teams.

Q: Communication is very important in a business with telecommuting staff. Do you have any special communication systems in place with your team?

02 Communicating with Remote Staff

It’s an expectation that all Remote Representatives are available through G-chat while on the clock.This constant communication helps me, as a manager, answer questions quickly and keeps the lines of communication open. It gives all Representatives, remote and in-house, the sense that we are all together in the same place.

GoToMeetings also help me train Remote Representatives. Through the ability to “share screens”, I’m able to keep remote representatives informed on updates, changes, and additions within our system.

To keep the team connected, I send a weekly email of everything that happened throughout the week. We are also implementing company-wide Morning Announcements. Each day we will record a 5-minute video clip to be sent out to all Lawyer.com Representatives. Included in the video will be the previous day’s numbers, incentives for the week, and company news.

Kristen Povolny
Lawyer Support Manager, Lawyer.com

WORK[etc] Tip:

The Discussions module allows you to create threaded, forum-style discussions where you and your team members can talk to each other without ending up with clogged email inboxes.

Discussions can be started from and attached to any object within WORK[etc] — from contacts and leads to projects and support cases — and will appear in that object’s activity stream.

For example, you need help handling a tricky issue that a customer sent a support ticket about. Start a discussion on that support ticket and get some fresh eyes and input on the problem — even from team members located halfway across the globe.

Q: How do you manage the workflow and measure the productivity of remote workers?

03 Managing Tasks and Measuring Productivity

Measuring productivity in a remote environment is difficult because people are not around physically and hence it’s difficult to get a sense of the efficiency levels. I manage this through tasks, i.e. a certain set of tasks are assigned including a mutually agreed upon time estimate.

If these are met, then the implicit assumption is that the team is efficiently achieving their goals — if not, then we discuss what went wrong.

Vivek Agarwal
CEO, Strand of Silk


We are able to manage staff work by using project management system. We track employees’ billable time — that is, time spent on actual client work.

Every week, full-time employees are required to clock in no less than 25 billable hours. Anything less than that and they just are not full-time. However, that also allows 15-25 hours each week for non-billable things such as team meetings, ongoing education, etc.

Stoney deGeyter
CEO, Pole Position Marketing


We tried lots of different things. We used those screenshare snooping programs but they are far too creepy.

Now, we use an automated Google documents script that generates a daily form for them to fill in with their daily summary. It contains questions about their day’s work and how much time they’ve spent.

Since I know how to do most things, I can tell if it seems they are padding it out. Most people are honest.

Eric Wroolie
Owner, Overpass Ltd

WORK[etc] Tip:

WORK[etc]’s integrated time tracking feature lets you and your remote team create timesheets that help you keep track of every billable hour and dollar. Going out for some field work? Install the native WORK[etc] apps for iOS and Android phones and never lose track of your billable hours again.


Goals and expectations are delivered up front; once expectations are clear, we trust people to simply achieve, without someone looking over their shoulder. That doesn’t mean they’re then working in a vacuum, however.

Despite the fact that we’re spread across the United States, many of our teams do daily stand-ups (progress reports about what they intend to get accomplished that day and what blockers stand in their way). All teams meet regularly, whether that’s every day, every couple of days or every week. We leave it up to the teams to decide what works best for them.

Each employee has a weekly one-on-one meeting with their supervisor (and in some cases others as well, like senior managers or department co workers) to talk about progress, inhibitors, goals or whatever’s on their mind.

Although we adhere to a flexible working schedule where people work when they want for the best results, we do expect people to be generally available whether online, by text or on the phone. Other than that, we manage remote workers the way you would manage any worker — by the results they produce.

All of our workers are measured on whether or not they’re meeting their goals. Like in any company, those vary depending on the department. The marketing team has different goals than the development team does, and how you measure success is different as well. Maybe a developer’s success is measured in terms of making something that works by a certain deadline, while a marketer’s success is measured in new customers acquired.

Either way, we don’t necessarily measure productivity; we instead measure success and goals met. An employee could work for 10 hours a day, just cranking out new features or content or ads, but if nothing produced helps us meet our goals, was it worth it?

We think the way to measure the success of any employee (and any business) is in terms of goals met. Every single person is responsible for working to meet those goals, so when one person is dropping the ball on assignments, it creates a chain effect, and it’s noticeable.

Ken McDonald
Chief Growth Officer, TeamSnap

WORK[etc] Tip:

You can instantly assign projects, subprojects, tasks, todos, and support emails to any member of your remote team using WORK[etc]. The system automatically notifies the assigned person, meaning they can immediately get to work on the tasks you’ve given them.

This feature is especially useful when used together with the WORK[etc] iOS and Android mobile apps. Let’s say you meet a potential lead make a successful elevator pitch while you’re outside the office. Just create the lead on the mobile app, choose a member of your sales team to assign the lead to, and voila! They can immediately start nurturing the new lead.

Q: How do you motivate remote workers?

04 Motivating Remote Workers

It is difficult to answer back-to-back calls all day, every day, but incentives help keep Remote Phone Representatives on task and motivated. We offer a bonus structure if certain goals and targets are met.

We’ve found that productivity drastically decreases when an incentive isn’t being provided. Now, incentive time periods are not announced. Remote representatives do not know when the bonus period is; they are expected to achieve those targets consistently. We have found this helps to maintain our numbers while also keeping representatives engaged.

Kristen Povolny
Lawyer Support Manager, Lawyer.com


Really, that starts with the hiring process for us. Because we work from a flex-schedule model, we are completely results driven. We don’t care how much or little time employees spend working; we care about what they achieve.

So we hire people who work that way — people who work for the end result, not the time put in. Those people are motivated by accomplishing their goals. Of course, it’s always nice to offer a little carrot, and ours includes unlimited vacation time and other great benefits like $1,500 annually toward education and a monthly gym stipend.

We have a low turnover rate; people want to work here and part of that is because we trust them and let them work how they want to.

Ken McDonald
Chief Growth Officer, TeamSnap


In an office environment, you see each other all the time and there’s inevitably going to be a lot of contact if you’re sharing a space. With a remote team, you don’t have that luxury, but it’s very important to set aside some time to communicate with them. They should feel their work is important and know there’s someone supervising them.

Frequent one-on-one meetings are vital to managing and motivating remote workers. My business partner David and I meet with ours once a day to go over what was accomplished and discuss what the next day’s plan is.

Marc Prosser
Publisher, FitSmallBusiness

Q: How do you build engagement and company culture with remote workers?

05 Building Engagement and Company Culture

I think the most important thing to remember is that our remote staff aren’t just names on a screen, they also have lives outside of work. As a manager, I try to stay interested and involved in their lives. I ask how their families are, what motivates them, and how they are doing personally.

I have found that this personal engagement creates an environment where each employee feels like the company cares about them. In turn, engagement increases and so does productivity.

Kristen Povolny
Lawyer Support Manager, Lawyer.com


From the beginning, a huge emphasis is put on the hiring process and finding good cultural fits. We look for people who are dedicated to being the best at what they do but also dedicated to living a full life, meaning work isn’t their whole life. We find the best employees are those who are passionate about other areas, whether that’s competing in triathlons, performing comedy, racing motorcycles, traveling or coaching youth sports (and we have people who do all of those things).

We also do things like hold Hangout happy hours, where employees get together via Google Hangout, enjoy a beverage and talk about the week. We use Slack to communicate daily via interest channels, like ones for recipes, living in an RV, and a “random” channel mostly used for sharing funny videos, stories or accomplishments. We emphasize communication, whether that’s just to say hi or to talk about a shared work project.

And twice a year, we get the entire team together in person for a four-day retreat that feels more like summer camp. We rent out suites in a hotel and split our time about equally between having company and department meetings and sharing in bonding time.

We cook dinners together and play games, and the best part is that it doesn’t feel like 60+ people meeting who barely know each other. Despite mostly speaking only online and only seeing faces via Hangout, everyone hugs, catches up and laughs as if we’re all great friends.

Ken McDonald
Chief Growth Officer, TeamSnap


For company culture, I stole an idea from my son’s preschool. Each week they have a ‘student of the week’. They send home a large piece of poster board, and the child is instructed to decorate it with photos of their family and their interests. Then they have to fill out a questionnaire about themselves.

We decided to incorporate the same idea into an online form. The team has had a bunch of fun with it, sharing where they went to school, their pets, funny stories, etc. Sounds silly, but you really get to know someone that way.

Bill Fish
President, ReputationManagement.com

Q: What were the biggest challenges you’ve faced managing a remote team?

06 Challenges in Managing a Remote Team

The biggest problem is internet issues and natural disasters. We had one typhoon last summer where the entire team lost electricity for nearly two weeks. I was all alone. Internet frequently goes down too . . . and without internet, there’s no communication at all.

Eric Wroolie
Owner, Overpass Ltd


Hiring is really the biggest challenge. We’ve found that when we find the right people, they blossom here.

For example, we have one junior developer who is making the transition to developing from being a paralegal. She’s eager to learn and has jumped in both feet first, not only in doing the best job she can but also in helping further our culture.

She regularly organizes team happy hours, contributes to our company blog and is the first to offer someone virtual condolences or congratulations. This was a great hire.

Of course, there are other people we’ve hired over the years that just weren’t able to get their heads around the remote aspect; they need someone to push them daily or tell them what to do and how to do it, maybe they felt a little isolated because they weren’t sure how to interact virtually.

In some situations it can just be hard to predict that this will be the outcome; in others, maybe we focus too much on a person’s skills and not enough on their personality. We try to get around this by really placing a lot of emphasis on the hiring process.

Potential employees can go through up to five rounds of interviews with various people, and although it seems daunting to them at the time, most of them get it once they’re in. We place a lot of trust in our employees, so we need to make sure they can handle it.

Ken McDonald
Chief Growth Officer, TeamSnap


One of the challenges I have faced is not being able to read the body language that you would experience in an office setting. There are times when people are slumping or walking around with their head down, and need someone to speak to.

You don’t have that luxury when you aren’t looking at someone on a day to day basis, so extra effort needs to be taken to ensure things are going well for the staff.

Bill Fish
President, ReputationManagement.com


Challenges usually revolve around trust and communication – but the two are related and proper communication can build trust easily.

For example, it is difficult for me to manage the pace of work and the tasks being undertaken by my remote team because it’s not easy to have a quick chat about issues being faced. This is of course easier if my team is sat in the same office as me.

Ample communication and timely communication can alleviate this issue — for example a daily Skype call with the team to quickly talk through issues being faced by them helps.

Retaining and motivating people is much tougher in remote situations, because they do not see the things that are happening in the company, they cannot be part of the culture, the jokes in the office or even able to get a clear strategic direction.

Our team member mentioned earlier had this issue. Since the company was young, there were a lot of changes that happened very fast, and it’s tough for someone not around to get a sense of these.

This led to her being de-motivated eventually, and also the fact that being remote, the chances of being part of senior management becomes limited. We did not manage to retain her for various reasons, but I believe that they key reason was the lack of visibility on the things that were happening in the company.

Vivek Agarwal
CEO, Strand of Silk


Managing a business with remote workers is nowhere near as easy as people think, but the rewards are great when done right. For a successful adoption of a remote working environment, it takes full commitment to a strong strategy founded on communication, collaboration, and culture.

What’s your top tip for working with remote teams? Share your thoughts in the comments section.

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