What to Know Before Hiring Your First Remote Employee featured image

Whether you’re struggling to find local talent or want to save money on office space, hiring a remote team could be the solution to your business’s staffing needs. However, operating a remote workforce also presents unique challenges for business owners. Here’s what you need to know before hiring your first remote worker.

Hiring Freelancers vs. Hiring Employees

Should you hire freelancers or employees for your remote workforce? The answer largely depends on the type of work you need done. While freelancers are ideal for one-off projects and temporary staffing needs, employees are best when you need permanent staff with a fixed schedule.

Businesses that hire employees are subject to a wide range of business laws, including worker’s compensation, the Family and Medical Leave Act, the Americans with Disabilities act, and employment taxes. Whether you’re hiring freelancers or employees, make sure you understand these laws and how they affect your business.Some business owners misclassify workers as independent contractors to skirt these requirements, but doing so could lead to trouble with the IRS.

Hiring Remote Employees: Qualities to Look For

In addition to the talents required for the job, workers need a unique set of skills in order to succeed in a remote team.

Screen for these qualities when hiring your remote staff:

  • Self-motivated: Self-motivated employees complete high-quality work and meet deadlines without frequent reminders.
  • Communicative: Remote employees are proactive about asking questions and providing progress updates so the entire team stays on the same page.
  • Highly organized: Daily routines and a focused workspace maximize productivity in a remote setting. Organized employees set priorities and minimize distractions.
  • Problem solvers: Since remote workers can’t lean over the cubicle to get a quick answer to a question, they find solutions to minor problems on their own.
  • Tech-savvy: Remote workers have a well-equipped office space and are comfortable learning software applications used to manage remote employees.

Assessing an applicant’s communication skills in an interview is easy enough, but other qualities are harder to gauge. For that reason, many businesses prefer to hire employees with experience working remotely. However, if your best candidate is someone with no history of telecommuting, there are questions you can ask to get an idea of their remote work capabilities.

Overcoming Challenges of Managing Remote Employees

Transitioning to a remote workforce changes how you communicate with and coordinate your staff. It’s a change that presents challenges to employers accustomed to working side-by-side, but with the right tools, your business can overcome these remote workforce challenges.


Successful onboarding is critical to the productivity of remote workers, but it’s difficult to train employees when you’re not there to show how things are done.

Develop an onboarding process before hiring your first remote employee. Account for paperwork that must be filed before the employee starts and the tools and software needed for the job in addition to employee training. Provide information in written and/or video format so that employees can refer to training materials as needed.


Remote employees still want to feel like they’re part of the company culture. There are a variety of ways businesses can encourage engagement and camaraderie amongst their staff, from using a chat app during the workday to scheduling weekly virtual meetings and quarterly in-person meetups.

Make a point to keep in close contact with any remote staff by setting up weekly meetings or calls to promote inclusion and ensure projects and work are on-schedule. Opt for shared file systems so staff have 24/7 access to project information, and have all meeting notes recorded and transcribed. This allows remote workers to read through or watch conversations in the event they miss a scheduled session or if they want to revisit an exact moment in a meeting.


A remote staff can span several time zones, leading to communication challenges. One way to handle this is setting hours for everyone based on a specific time zone; for example, if work hours are 8-5 PST, East Coast employees would work 11-8 to match. However, this scheduling dynamic can be frustrating for workers.

A better solution is allowing flexible schedules but establishing regular meeting times for answering questions and resolving issues. Scheduling and time-tracking software make it possible to know who is working when and monitor productivity within a flexible scheduling system.

With the right team and the right tools, working with a remote staff isn’t all that different from sharing office space. Water cooler chats become instant messages and weekly meetings happen at the computer instead of the conference room, but as long as your team is communicating and collaborating, your business will thrive no matter where your staff is located.


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