5 Lessons From 5 Years of Managing Remote Workers

5 Lessons From 5 Years of Managing Remote Workers
Image credit: Shutterstock

Free Book Preview: Coach ’Em Way Up

Discover how to be an influential mentor through tips and advice based on the teachings of respected basketball coach John Wooden.
CEO, Single Grain. Founder, Growth Everywhere.
5 min read
Opinions expressed by Entrepreneur contributors are their own.

I’ve been working with remote employees for years, and because of the great experiences I’ve had, I’m not surprised to see the statistics that describe how beneficial this arrangement can be:

Related: 4 Myths Debunked About Employees Working Remotely

What have you got to lose, right? Well, before you jump on the remote-employee bandwagon, there are a few things you’ll want to consider to make the transition as smooth as possible. Here are five lessons I’ve learned from capitalizing on this powerful work arrangement for the past five years:

1. Clearly define your job descriptions.

Hiring for any position requires clear job descriptions, but there are two reasons why it’s especially important for remote positions:

  • isn’t for everybody. Being able to stay motivated outside of the office requires a special type of candidate. By making your expectations for a remote position clear up front, you enable prospective applicants to decide whether the job you’re offering will be the right fit.
  • You won’t be there in person to explain the nuance of the position. With an in-office employee, you can explain position requirements as you go. While and videoconferencing help onboard remote workers, it’s not as if an out-of-office worker can just pop by your desk unannounced. Being clear about your expectations up front makes the process easier for everyone.

2. Hire the right workers.

As I mentioned above, remote work isn’t for everyone. Some employees will be unable to resist the pull of a mid-day I Love Lucy marathon, while others are too social (or prefer a more hands-on style) to thrive in this setting.

Hiring the right remote workers requires a few extra steps to your hiring process. The first is to be sure you’re asking the right interview questions. In addition to your usual queries, include the following:

  • Do you have experience working remotely?
  • What do you do to remain productive in a remote setting?
  • When working remotely, how do you handle projects with unclear instructions?
  • What steps would you take to connect with other members of the remote team?

I’ve also found it helpful to give remote candidates a test project, such as putting together a content-promotion strategy. The results of this “homework assignment” give me some insight into whether they’re cut out for the arrangement. Face-to-face video interviews are also helpful for this purpose, as candidates’ body language tells you a lot about what they’re really thinking.

Related: Hard-Earned Lessons From Building a Remote Culture

3. Onboard effectively.

When you onboard traditional employees, you have to set up their desks, buy or install computers and show them around the office. With remote workers, the process is a bit different, but it’s just as important.

One of my favorite tricks for remote workers is to set up an internal wiki that covers things such as where to find company information, who can answer your various questions, what tools the office uses and so on. We use Hackpad for Single Grain’s internal wiki, and the fact that we have all our internal documentation centralized -- including screencasts showing how different tasks are performed -- makes it easier for new remote hires to get up and running.

4. Use the right tools.

In addition to Hackpad, we use the following tools at Single Grain to keep our remote team connected:

  • We use Basecamp for client communications, the delivery of client documents and external . Keeping all client communications here prevents important information from getting caught in somebody’s inbox.
  • Trello is our internal project management system. It’s great for managing temporary and recurring projects that involve multiple people and multiple action items.
  • Slack is our internal office tool, which we use to ask easy questions, share links and files and goof off as a team.
  • Although Slack has many of the same capabilities, I prefer Skype for one-on-one meetings or longer conversations that require screen sharing or collaboration.

Basically, your tools will make or break your remote work arrangement. Don’t be frugal about the programs you need.

5. Don’t skimp on face-to-face time.

Finally, although by nature remote work involves less face-to-face time than in-office workers, I’ve found that you can’t give it up entirely. Depending on the worker and the position they fill, I try to connect one on one with each of my remote workers weekly or monthly. Doing so helps me catch small issues before they become big issues and increases the sense of loyalty my remote employees have to the company.

Certainly, managing remote workers effectively requires more than these five lessons alone, but this should be a good place to start if you’re considering virtual arrangements. If you’ve been working with a remote team and have another tip to add to this list, share your thoughts by leaving a comment below.

Related: How to Keep Your Remote Workers Connected

More from Entrepreneur

Get heaping discounts to books you love delivered straight to your inbox. We’ll feature a different book each week and share exclusive deals you won’t find anywhere else.
Amplify your business knowledge and reach your full entrepreneurial potential with Entrepreneur Insider’s exclusive benefits. For just $5 per month, get access to premium content, webinars, an ad-free experience, and more! Plus, enjoy a FREE 1-year Entrepreneur magazine subscription.
Create your business plan in half the time with twice the impact using Entrepreneur's BIZ PLANNING PLUS powered by LivePlan. Try risk free for 60 days.

Latest on Entrepreneur