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How Do You Manage Remote Workers for Optimal Productivity?

I’ve used remote workers and freelancers the build and maintain several businesses over the last 15 years. My current business is comprised of remote workers scattered all over the world.  

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Even though we’re separated by thousands of miles and different time zones, our roles in the business haven’t changed. We still have metrics and sales goals, and I’m still their boss and CEO. Maintaining those relationships over distance and helping my workers succeed is always at the top of my list, but it’s not without some difficulties.

Top challenges when managing remote workers

Here are a few challenges that come with having a remote workforce and how to overcome them:

Communicating with a remote team

No matter your business, its size, or whether you have in-house or remote teams, communication is always key. My remote teams can’t just walk down the meeting room, and they don’t have a way to socialize with one another without tools.

We use services like Slack in order to stay connected. The immediacy of instant messaging and the ability to review the messaging history is a great way for everyone to stay connected, but it’s not enough.  I like to have weekly meetings over video chat to solicit ideas and give the team a chance to interact with one another in real time.

Because distance is such a factor, I actively promote these tools and do my best to maintain an open-door policy with my team. I want them to reach out to me with their ideas, and I want them to know that I’ll listen. In an office, some of those signals are implied. With a remote team, actively pursuing open communication is important.

How to hold your remote workforce accountable

My teams are still accountable for the work they produce. My sales agents have metrics to meet, and my programmers have products to build. As CEO, I still need to be able to track them. This is easier than it might seem.

For producible work, it’s my job to review the product when it’s submitted. If a web developer submits updated code for our website, I review it and supply feedback. When sales and customer service work is happening in real-time, I use tools like RingCentral to ensure that my workers have the tools they need to carry on great interactions. I can even provide feedback, as needed, by reviewing and recording calls.

Hourly tracking is another challenge. I like to know when my workers are working, even if they’re salaried.  We use the desktop time tracker from Upwork, though if you are not using a platform to pay workers, TimeDoctor is great for this. The software not only monitors hours. It can also track screen and monitor chats, as well as generate reports that will help you improve productivity.

Ensure your company is secure

Whether you have an irate employee or a freelancer who just turned out to be a bad fit, security is important when maintaining a remote workforce. In an office, you might have security escort someone out of the building. With a remote team, it’s not that easy.

A remote workforce means allowing access to critical components of your business. While you may never have to use it, taking the appropriate steps to limit access and knowing the best ways to lock workers out of your systems is an important step in managing a remote team. As a CEO or team leader, your ability to manage that access and remove workers quickly is your ability to safeguard your business.

However, using those tools isn’t enough. You should also create and safely store backups of all critical information that remote workers have access to. I had a remote worker once who, upon receiving feedback that he wasn’t doing a great job and was being let go, tried to erase all the work on my website. He managed to do it, but I had a backup of the data and restored it with no break in service.

How to ensure your remote workforce is engaged

Keeping employees actively engaged is one of the biggest challenges of a remote workforce. In an office, people might form natural friendships due to proximity, but remote workers are often alone in an empty room with a chat window and a task manager.

At True Blue, I actively work to grow and maintain a strong employee culture. I’ll often encourage my employees to collaborate with one another to solve problems. We talk up our successes, and I make it a point to give workers praise in places where other team members can celebrate with them.

Because we don’t have employees bouncing ideas off of one another or engaging in small talk without the use of online tools, friendliness and attitude are big factors in my hiring decisions. One of the best things I can do for my team is to make sure they all get along. If someone doesn’t get connect with the team or just has a bad attitude overall, it’s a hiring risk. If they’re already on the team, I’ll replace them before they drag the whole team down.

Concluding thoughts

It’s true that having a remote team has its challenges, but they aren’t unique to remote work. They’re only different due to distance.

With remote teams, it’s important to keep those factors in the back of your mind and adjust your business strategies accordingly. If you can do that, those challenges are easy to overcome. 


Brian Greenberg is a multi-faceted entrepreneur currently serving as vice-president, co-founder, and founder of multiple online businesses. His online insurance brokerage—True Blue Life Insurance—has grown steadily since 2003. They now sell insurance in all 50 U.S. states via his website. He is recognized as one of the most creative people in the insurance industry and serves as a member of the Million Dollar Round Table, a premier association that represents the top one percent of financial professionals.

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