How to Overcome the Challenges of Managing a Remote Team

  • 5 min read

I’ve been using remote workers in my business operations for over 15 years. During my first decade in business, I didn’t have an office, so I relied on freelancers and remote workers for everything from web development to sales calls.

To date, I’ve spent almost a million dollars on freelancers. In addition to managing them remotely, I’ve taught them how to manage their own remote teams!

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Remote workers have a lot of advantages for your business and there are several ways to track their productivity from behind the scenes. Properly run, freelancers can be the most cost-effective way to complete a project.

How to keep remote employees engaged in your company

Here are a few tricks I’ve learned that will help keep your remote employees engaged and productive.

Hire the best people

One of the biggest advantages to remote work is that you can hire employees from anywhere. This gives you some unique options when you build your team.

If you want to serve customers in a specific time zone or local area that you don’t currently support, using remote workers to fill those jobs can provide added versatility. When you need to enhance your e-commerce platform or create a custom software solution, offering those jobs at competitive prices can attract high performers from around the world.

Remote employees and engagement

Photo source: A Study of 1,100 Employees Found That Remote Workers Feel Shunned and Left Out (Harvard Business Review)

You should still interview, just as you would hire an in-house employee.

When I hire a remote worker, I always conduct the initial screening and first interview over the phone.  I may use a messaging platform to chat with them initially. However, I’ll always ask for a phone call or a video conference before awarding the position. This is a great way to filter out potential hires who aren’t interested in your operation and to make a personal connection with those who are.

A remote interview has to be just as engaging as an in-person interview. I want to get a feeling for who I’m hiring, and I want candidates to ask questions and provide feedback. If I want them to be part of a team, I introduce them to the team leader in a second interview and make sure they’ll be a good fit.

Most importantly, if they’re a great fit, I want them to feel like they’re part of my team.

Use the best tools.

In the past few years, cloud-based services have done wonders to assist remote collaboration and productivity.  In the early days, my teams used to send documents via email. Today, we use the Google Suite to collaborate on documents in real time.

If your business is considering a move to remote work, even partially, consider changing the tools you use to better suit your needs. Productivity platforms like Slack offer instant messaging, calling options, and video chat to replace office meetings. For project management, Meistertask is great for keeping teams on track.

For sales teams, I prefer RingCentral. From their administrative platform, I can see when my agents are on the phone. I can listen to their calls, talk to them in real time while they’re on a call, or simply record the call and give them feedback later.

For my teams at True Blue Life Insurance, I conduct weekly video conference meetings using It is important to see your team and let your team members see each other. It creates a bond that is comparable to working in the same office.

Use tools that provide quick access to essential and up-to-date information that your remote workers can access on their own. Your people and your bottom line will thank you for it.

Be the best boss.

I’ve used all the major freelancing websites to find great hires for my business, but one of the first discoveries I made when I started hiring freelancers was that I couldn’t demand exclusivity. A freelancer can take other jobs on the side, and there is always the risk that one of my veterans could leave because a competitor offered a better rate of pay or a perk I didn’t provide.

I realized quickly that one of the best things I could do was to offer something that made working for me more appealing than working for a competitor. We offer a team environment where they feel valued and safe to voice their opinions.

As a CEO, I also invest in their future by providing mentorship. I have quarterly meetings with each team member to go over performance. We then discuss ways in which they and management can improve. While this feedback has been invaluable to my business, it also gives everyone the opportunity to feel like they have a stake in the success of the company. their project.

Wrapping Up

My company has a slogan: ABN — Always Be Nice. Some companies have ABC — Always Be Closing.  We have ABN. I believe that actively developing your team isn’t just a nice thing to do. It’s something you should do whether your employees work beside you or on the other side of the world.  

When you hire the best people you can find, give them the best tools to do their jobs, and do your best to help them grow,  you’ll find your remote employees will give you their all, every single day. 

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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  • Originally published January 23, 2019, updated April 26, 2023