5 Lessons Learned from Managing a Remote Team


This is a guest post by David Waring. David has several successful websites aimed to help business owners. Here, he discusses important lessons he's learned from managing a remote team.

Image by Unsplash.
Image by Unsplash.

With the evolution of the internet and today’s collaboration technology, the workplace has gone global: it’s no longer uncommon for employees everywhere from Dubai to North Dakota to work for companies based in New York City or anywhere else in the world.

My business partner and I started Fit Small Business with a completely remote team, and that team had a huge role in building the business to where it is today. We’ve since opened a physical office in New York with a growing staff of on-site workers, but we continue to work with our remote team on a daily basis.

Here are 5 lessons we learned from managing our remote workers:

1. Treat Project-Based Interviews Differently from Full-Time Hires

Many businesses, use remote workers specifically for project-based work. We use remote workers for both one-off projects and ongoing full-time work.

When we hire full time works for our business we are very thorough with the interview process. After all, this person will be putting in thousands of hours of labor for our business. When hiring remote workers for project based work however, putting that kind of time and effort into the interview process is unnecessary. The stakes are simply not as high. If a project goes poorly, you can always move on with the next project and hire another freelancer.

For project-based hires, I typically assign a small test project. Let’s say I want a guide written about setting up a retail store. I take a small section of the guide, such as the part on the retail floor layout, and ask each interested freelancer to submit a short test piece on that subject. Normally, one emerges as the clear winner and then I assign the entire project to that freelancer.

2. If You Are Hiring A Full-Time Remote Worker, Interview Thoroughly

With the above being said, if you’re hiring a remote worker for a full-time position, you should interview them just as you would any other full-time hire.   

We have a pretty intensive interview process. We ask for resumes and also create a survey using Wufoo with several questions for candidates to answer.  Surprisingly, just asking people to fill out a short survey helps weed out many sub par applicants; for one recent position, we received over 1000 applicants, but only a third filled out our three-question survey. From their, our process is as follows:

  1. I do a video interview with the most promising candidates
  2. My partner does a phone interview
  3. We assign a test project
  4. We make an offer

The process is fairly involved, but so far it has produced reliable, loyal, and effective remote workers for us.

3. Communication is Key: Define Clearly What Is Expected and What A Remote Worker Needs to Accomplish

As with any relationship, communication is key. This is especially true with remote workers, since you are not seeing them and interacting with them everyday in the office. Make an effort to have regular conversations and video calls with remote workers, especially with those that are working for you on an ongoing basis.

Most importantly, be clear concerning what you expect from them and what they need to do to “accomplish their task” in your eyes. Be specific but kind, offering helpful critique. Be sure to verbally affirm when something is done well, especially when you are just beginning to work together. That gives them the confidence and motivation they need to stay on-task despite not being in a formal office environment.  

4. Have a Consistent Submission and Productivity Measurement Process for Remote Workers

Consistency is absolutely key when managing remote workers. That’s why we have a consistent and specific way for our remote team submit their work, just as a full-timer would. We also assign point values for every article or project our ongoing freelancers complete. At the end of each week, we assess the point values. This gives a pretty consistent way to look back and measure the overall productivity of a remote worker. This is helpful in two ways:

  1. It Gives Remote Workers a Concrete Goal - As mentioned above in point 3, this is all about making sure everyone is on the same page and knows what needs to be accomplished by what date. A point system gives remote workers a concrete goal to shoot for, which is especially important because they are not sitting beside you everyday in a position where you can easily review and discuss what needs to be done.
  1. It Gives You Positive Leverage as a Manager - If a worker needs to be let go or taken off a job for consistent underperformance, a point system provides an unbiased record that you can reference. Also, it helps for promotions, bonuses, and other rewards.

5. Use Collaboration Tools

Collaboration tools are the last key piece of the remote worker management puzzle. There are so many different tools you can use to make managing your freelance employees easier. Here are some we use every week.

  • Google Chat, Google Hangouts, Skype - We talk with our ongoing freelancers nearly every day. It’s easy to work out a small concern over chat. If it is more involved, we’ll talk face-to-face via video chat or Google Hangout. Also, we have a weekly meeting as a team on Google Hangouts, which supports multiple video chats all in one window. These tools are all free to use, which is another big plus.
  • Insightly - Insightly is a CRM system that also offers great project management capabilities. All of our projects, leads, and productivity tracking are managed in Insightly. Our employees and freelancers input tasks into Insightly and we can track them from start to finish. You could use a dedicated project management software such as Basecamp or Trello, but for our needs, we prefer to keep our project management in the same package as our CRM.

Summing It All Up

Consistent communication and clear expectations are the most important parts of managing remote workers. If you succeed at those and follow the guidelines listed above, you will be well on your way to efficiently managing your remote workers.

David Waring HeadshotDavid Waring was the Managing Director of Business Development one of the first employees at Forex Capital Markets LLC, which he helped grow to over 700 employees as .  Since then, David has launched several successful websites. His flagship site, Fit Small Business offers small businesses the information they need to make the best decisions possible. His most recent project, Fit Biz Loans, helps connect small business owners and entrepreneurs with a variety of lenders so that small businesses can get the least expensive loans possible.

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Bolton Remote

Bolton Remote helps businesses grow with dedicated remote teams. To find out more about remote staffing, visit BoltonRemote.com.
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About Bolton Remote

Bolton Remote helps businesses grow with dedicated remote teams. To find out more about remote staffing, visit BoltonRemote.com.