Hiring a Remote Worker? It Takes More Than an Internet Connection

Being online is a must — but so is defining “remote,” understanding state laws and standardizing interviews.

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Federal data continues to show near-record numbers of job openings across the country. As of April 2022, 33.4% of business owners were still having trouble hiring paid employees, according to the most recent Small Business Pulse Survey from the U.S. Census Bureau.

If your business has an open seat for a work-from-home job — or one that could be — a remote worker may help fill it. But before that can happen, you’ll need to handle more than just basic barriers, like equipment or cybersecurity. Here’s what you need to know to hire a remote employee.

1. Figure out the logistics

If you hire an employee in a new state from wherever your small business currently operates, you’ll be subject to that state’s employment laws and payroll taxes. You’ll also need workers’ compensation insurance in each state where you have employees.

The more far-flung your team gets, the more likely you may need to hire a human resources staffer, consultant or vendor — eating into your budget for new roles.

“If you want to keep things simple, stay within your state,” says Megan Dilley, communications director at Distribute, a consulting firm that specializes in remote work.

You can also turn to a freelancer-for-hire service like Fiverr or Upwork to simplify the hiring process.

Tessa Gomes, a Hawaii-based wedding planner, hired a team of five contractors through Upwork earlier this year.

“It just makes so much more sense than me trying to do it individually,” Gomes says. “It’s like [my] pool of human resources just grew tenfold.”

2. Define your company and the role

When writing your job description, make sure it includes details about your remote-work environment.

“The definitions [of 'remote'] are all pretty fuzzy,” Dilley says. “So as much as you can, be very clear and transparent from the get-go.”

For example, if you expect employees to clock in at 9 a.m. Eastern time each day, to come to the office twice a week or to travel for a quarterly meeting, say so on the job listing.

Polish up your company website and social media profiles as well. Consider adding some information about your employees and your work environment.

Each company should make sure its online presence explains “who they are, their brand, what their culture is like, how they treat their people, DEI,” says Victoria Neal, an HR knowledge advisor at the Society for Human Resource Management.

You can list job postings on LinkedIn and other job board websites, but Neal says to try sharing job postings through social media or email among people who already follow your work.

“A lot of employers are really utilizing their current user bases” to find new hires, she says.

3. Redesign your interview process

Because interviewers may no longer see candidates in person, you’ll need to educate them about new things.

“Virtual recruiting and virtual interviewing can eliminate some biases,” says Allan Platt, CEO of business consulting firm Clareo. But he adds that they can introduce a whole new set of assumptions, for instance around candidates' internet connection and home office setup.

To help with this, Platt says his company’s interviews are highly structured and candidates are evaluated on consistent matrices.

“The way that we structure and organize our interviews when we're doing remote interviews is really important,” Platt says. “Candidates are evaluating us as much as we're evaluating them. They're looking for every clue they can get.”

You may also want to tweak your interview structure. For instance, remote workers need to be excellent communicators who can meet deadlines. Asking behavioral interview questions and assigning sample work can help you find candidates who demonstrate those skills.

4. Prepare for day one

Before your new hire joins the team, make sure your workplace operates well asynchronously. Online tools for remote work like Slack can help employees help each other, so a new hire’s manager doesn’t have to field every question — especially if their working hours don’t line up.

On day one, you can help your new employees feel welcome and fully prepared by planning an onboarding program. If you don’t already have documentation for common processes, try to create it before your new hire starts.

Schedule frequent meetings with your new employee at the beginning. As those meetings taper off, Dilley encourages over-communication as the norm.

Spend some time thinking about your own mindset, too. If you’re used to having constant contact with a new employee — especially during their first few weeks — prepare to give up some control.

With remote work, “trust is assumed and not earned,” Dilley says, “which is a bit of a difference in what people used to talk about.”