remote workers

Challenges Remote Entrepreneurs Face and How to Overcome Them

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The following is excerpted from “Back to Human: How Great Leaders Create Connection in the Age of Isolation” by Dan Schawbel. Copyright © 2018. Available from Da Capo Lifelong Books, an imprint of Perseus Books, LLC, a subsidiary of Hachette Book Group, Inc.

With more and more employees choosing flexible work arrangements, chances are good that you’re managing one or more remote workers now or you will be in the not-too-distant future. But although some people might think that managing someone they rarely see would be easy, it actually takes a lot of skill. Collaborative technologies can be useful for maintaining contact with your remote workers, but it’s your responsibility to create a more personal relationship with them by phone, in‑person visits or videoconferencing.

When remote teams are disengaged, it’s almost always the manager’s fault. In one study, a fourth of virtual teams were ineffective due to poor management. Highly effective teams, however, had management who promoted accountability, motivation, purpose, process, and of course, relationships. Managers of the most successful teams have a consistently open line of communication with their employees and ensure that those employees know what’s happening in the organization and have the tools they need to succeed.



Remote workers face a number of unique challenges. First, they’re much more likely to feel isolated, lonely and depressed because they have less human contact than your other employees. Second, they have many more potential distractions around them, such as noisy people in a coffee shop or their kids playing video games in another part of the home. Third, although their intention behind working remotely was to have more flexibility, they often end up losing track of time and working around the clock. When you’re in an office, you have a more defined workday because you see people coming and going at around the same time every day.

You won’t be able to overcome all of these challenges, but you can definitely help by giving remote workers regular attention. Be sure that your goals and your telecommuting policy are clear so there won’t be any issues later. Explain how important remote workers are to the whole team’s success and ask for regular updates so remote workers get in the habit of checking in with you. Make sure you aren’t just relying on high-tech collaboration tools to engage with them. Instead, schedule at least one weekly phone meeting or videoconference so you can maintain an emotional connection with them and ask whether they have any project updates or need help with anything. Issues that don’t get resolved quickly can fester and quickly become much bigger problems.

“Whenever there’s a lag of communication across a remote workforce, people fill that void with assumptions about what’s happening or not happening in the business, and with rumors, and they feel very disconnected and very uneasy about the business,” says Rajiv Kumar, president and chief medical officer at Virgin Pulse. “Constant communication—and never leaving remote employees feeling like they’re on an island—is critical,” he adds, “whether it be company-wide town halls, webinars, emails, PowerPoint presentations, updates on health of the business, social emails, [or] announcing accomplishments.”

If you want to take things a step further, consider mandating that your remote employees come to the office a few times every year. While this may seem harsh, it’s for everyone’s benefit, because the extra face time will result in deeper relationships. Antonio McBroom, the chief euphoria officer at Ben & Jerry’s, told me that he requires that remote workers “travel to their primary place of business quarterly to reinforce our team dynamic and the importance of the work we’re doing.” In addition, “any professional development or beyond-the-job opportunities that we have at our home office, we also try to incorporate the parallel for remote workers.”

Empower your remote workers by giving them plenty of autonomy and control over the projects you assign them. Micromanaging may seem like a good way to engage them on an ongoing basis, but many people telecommute for the freedom and opportunity to do projects independently. As long as they’re producing quality work, give them the flexibility to do things their way. I know it sounds a little counterintuitive, but this will make them feel more included and will encourage the rest of the team to engage more with their remote colleagues.


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As you know, my goal in this book is to push you to increase the degree of human connection you have with your teammates. However, it would be absurd to ignore the powerful role technology can play in facilitating communication and collaboration. When you have remote workers, technology can be a vital asset—as long as you use it properly. If you select the right tools, train your employees on how to use them, and then leverage those tools when collaborating, you’ll be more successful. If you champion a tool and then fail to use it, your team will eventually stop using it, as well. Some tools can limit the often-overwhelming flow of emails we receive every day and enable us to communicate more quickly and efficiently with people who aren’t at our location. Use these tools for real-time dialogue and to promote your weekly staff meetings for both your traditional and your remote employees.

Finally, try not to treat remote workers differently than your traditional employees. A lot of leaders pick favorites (usually people they see every day), leaving remote workers feeling they can’t succeed or aren’t getting as much attention. That’s why it’s so important to show empathy and concern for your remote workers’ well-being and to ensure that they’re achieving their personal and professional goals, not just the team goals you’ve set for them.

“Back to Human” is available now at fine booksellers and can be purchased via StartupNation.com.

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