9 Tips for Managing Remote Employees in Small Businesses

Today, many businesses utilize remote freelance employees to help increase productivity, and to outsource tasks that can be completed independently. Hiring remote full-time employees can also be an excellent way for businesses to gain access to talent around the world, rather than limiting their talent pool to certain regions. Advances in communication software like Slack have made it easier to collaborate across distributed teams—but managing remote employees still presents considerable challenges, ranging from trying to establish rapport, to ensuring that remote employees are well-equipped to become as productive as traditional employees.

To help reduce the learning curve associated with successfully managing remote employees, we spoke with 9 small businesses that have expertise in this area, and asked them to share their best tips for establishing a successful working relationship with remote employees.

1. Take an interest in your freelancers' career development

Jake Tully, Head of Creative Department, TruckDrivingJobs.com

In my time as creative department head at TruckDrivingJobs, I have been a project manager for several different teams of employees, some in-house and some remote. In managing remote employees (mostly in a freelance capacity) I have been lucky to run into very few issues in getting work done or receiving high quality work.

With that in mind, I have found that communication is key in managing remote freelance employees, but what is more important than simply communicating is communicating with the intent of getting to know employees and seeing how goals might align with one another. It's one thing to check in with a remote employee to see how the progress of a campaign or project is coming along, but it's another thing entirely to open up channels of communication with an employee to see what they want to accomplish from completing a project, rather than just getting paid for completing their tasks.

It's a good idea to have a discussion with employees about the nature of mutual goals to ensure that the quality of work achieved is satisfactory on both ends, as well as ensuring that there is a positive line of communication between both parties. When a remote employee feels as though their work is valued as well as feeling like their intentions and goals are valued, everyone wins.

2. Bring full-time remote employees on-site to establish rapport

Kean Graham, CEO, MonetizeMore

We have only hired candidates that have a track record of thriving in virtual environments. They have the ability to engineer their perfect lifestyle by choosing their schedule and living anywhere in the world. With the ability to live a dream lifestyle free of commuting, team members can produce results dramatically higher than they did when they worked from an office.

The majority of our team meets once a year. In a perfect business world, being virtual forever would work just fine. However, there is still value in establishing rapport in-person and participating in team building activities while everyone is in the same location.

We have a company culture document that we show every candidate and continually refer to with each team member. This document serves as rationale for a lot of our decision-making and we encourage our team members to provide constructive criticism to other team members based on this document. An office naturally evolves a culture. There needs to be a greater cerebral effort to grow a purposeful culture within a virtual office.

3. Test the waters before committing to an employee working remotely full-time

Sam Underwood, Business Strategy Director, Futurety

We prefer to bring on remote employees as contractors prior to officially hiring, for a period of 30-60 days. Typically, we find that prospective employees show their true colors after this 2 month "break in period" and we can get a good read on how they would perform in a permanent role.

Cloud-based tools are a huge help in managing remote employees. We use Trello and shared G Suite calendars and documents extensively to help our remote employees manage tasks collaboratively with our team members in the office.

Video conferencing rocks! Our remote team members love it when we can include them via video conference, even if we're doing an employee lunch or something more casual. We use Google Hangouts a ton.

4. Gradually increase their responsibilities

Jeff Moriarty, Mothers Family Rings, Marketing

We are a small jewelry business located in Crown Point, Indiana with three remote employees: two are contractors and one is full time. The main reason we hired remote workers was because we couldn't find good enough talent in our area. We are not located near a huge city, but instead in a small town. This makes it very hard to find the talent we need. Hiring nationwide for one position and worldwide for two others allowed us to get the talent and experience we needed

Managing remote employees is tougher as you have to be able to really trust them. With us, if we see constant improvements in results and see projects are being completed in a time we feel is right, we believe that our money is being used wisely on that employee. We also have Skype open to chat with them and have weekly meetings to go over projects. The key is being in constant contact with them. This makes them feel like they are just in another office across the way.

We have went through quite a few remote employees over the years as it is not easy find reliable remote workers. But the three we have now we have had for over 3 years and are very happy with them!

5. Conduct regular 1-1's with remote employees to identify areas for improvement

Jeff Kear, Co-Founder, Planning Pod

A great practice we've implemented is to conduct a weekly "lessons learned" session with each remote worker to go over their work and challenges from the previous 5 days. Every Friday at Planning Pod, each supervisor holds a 30-minute "lessons learned" session with each employee as a regroup for the week to cover where things went right and went wrong. This gives remote workers an open forum where no judgements are made but where they can learn from their successes and mistakes, so their supervisors can get a better grasp on where they are having difficulties and can address them before they grow into chronic problems. At the end of each session, the employee and supervisor create a short list of action items for the employee to address, and in the following week's session these action items are revisited to make sure the employee has been addressing them in their work.

6. Hire self-starters

Cynthia Rowland, Founder & President, Rejuve, Inc

As a small business owner who uses remote employees, I want to let other companies know that this can be an excellent way to gather great people who may not be local to your business. I founded Rejenuve, Inc. in 1992 and have been using remote freelancers for at least ten years. It’s not always easy to find reliable people, as we all know, so when I found my current freelancers, I knew I wanted to work with them as much as possible.

One concept that has worked well with managing our remote freelancers is the weekly report, in addition to the weekly video meeting. On Fridays, each of them provides us with a pdf report of their accomplishments for the week. We don't want to suffocate our people by tracking their every move, of course. The weekly report allows us to hold them responsible, while keeping everyone organized and on track with the week’s projects.

Since remote employees are required to be more independent than on-site employees, it's crucial to hire remote employees who can work independently. We have a strategy for hiring self-starters, which we learned from a Forbes article published in 2016. Asking the open-ended question, “Could you tell me about a time when your work held little or no interest for you?” can reveal whether the freelancer is a self-starter or someone who needs prodding from their manager.

7. Do your due diligence when hiring

Chris Van Patten, Owner & Creative Director, Tomodomo

Businesses considering hiring remote employees should make sure they give the hiring process as much attention—if not more attention—as they would when hiring an employee in person.

One of the biggest challenges when hiring is finding people you'll get along with and work well with, and this is compounded dramatically when hiring remote workers.

That's not because it's harder to get along with people remotely; it's just that it can be much harder to tell what someone's like if you aren't with them in person. You miss out on a lot of visual and emotional cues that can be a sign of someone's work ethic, "bedside manner" (especially important when they'll be communicating directly with customers and clients), their compatibility with your company culture, etc.

For example, I once had a very bad experience with a developer I hired for a project. At the time, we only conducted email and text chat-based interviews. Because they had the technical skills our project required, and thus were able to answer all my interview questions correctly over email, I never took time to speak with them on the phone or via video.

After the project started, and we began having team meetings, it became clear we had a problem. The new team member was combative and rude to other team members during the calls. They spent time complaining about other team members instead of focusing on the tasks at hand. I was approached privately, multiple times, by the other members of the team. They were all frustrated and concerned about the effect the new hire was having on morale.

Ultimately it was clear the hiring was a mistake, and I had to let the new developer go. But it taught me the importance of being very thorough in the hiring process, and making sure to include phone and video calls as key parts of the hiring process. Now we only use email to coordinate the phone calls; other than those emails and a small survey at the beginning of the process, all communication happens via Skype. As a result of that change, our team churn has dropped dramatically!

8. Be mindful of those with disabilities

Dana Marlowe, Principal Partner, Accessibility Partners

I don’t just work with one remote employee, I have about a dozen! I manage a few teleworkers, and we provide the budget to create their own workstations, but leave it up to them to choose their own arrangements. At Accessibility Partners, we are firm believes of Bring Your Own Device (BYOD) and have implemented a strong policy.

With a staff comprised of people with disabilities working all over the country, we let them make their own accommodations for productivity. Within Accessibility Partners, we’ve seen that when an employee purchases an item like a tablet, computer, or phone, they can create a device that truly works for them.

We want all of our workers with disabilities to be successful and productive, and they know what works for them. It’s unfair and impractical to assume a one-size-fits-all mentality with technology, and sometimes you just have to trust a user. They know their abilities and situation better than anyone and our workforce is extremely productive because of it.

9. Leverage project management software and group chats

Asaf Darash, Founder & CEO, RegPack

I have four remote employees, consisting of a mix of freelance and full-time employees. However, I came about this from the opposite side: I didn't hire remotely, but employees who were in the office needed to leave the city and we arranged for them to stay on and work remotely. Additionally, my director of marketing has always been remote. She began as a freelance social media manager and blog writer and grew over several years into a full-time role.

While I might not have initially sought to have remote staff, I have to say it works just as well as if they were in the office. I would imagine it depends on the type of company, but for us, as a registration software (SaaS company), we have no issues.

We are able to conduct staff meetings as a conference call. As far as team collaboration, we use an online project management software anyway to manage projects and communicate on them mostly through comments on tasks and via chat in the office. We use group chats for specific teams as well, as this helps streamline communication and ensure everyone is in the loop. The side benefit to this is that someone who is out of office permanently or working from home that day is just as productive and connected to what is going on since this is our standard process.

Lastly, since all of our communication with clients is conducted via phone and email, as long as you have an internet connection and a laptop you can work just as efficiently in or out of the office.

I've made it a point to have all remote workers flown in once a year for a few days so we can do some team bonding events and just generally be together and have "big picture" meetings.

Allowing some of our staff to work remotely has proven to be a great choice. They feel valued as team members since we are able to offer them the support and flexibility they need. And, as our team has grown, having some people remotely has put off the need to move offices as we need more space since some of our team aren't in need of office space. This is an unintended bonus, but it has worked out well for the past 2 years!

Bruce Hogan

Bruce Hogan is Co-founder & CEO of SoftwarePundit. He leads the team's research and publishes content about software products and trends. Bruce has experience investing at multi-billion dollar private equity firms, leading teams at venture-backed technology companies, and launching new businesses. You can connect with Bruce on LinkedIn.

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