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Tips for Hiring Remote Workers for the First Time

Erik L. Anderson Insurance Agency

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Jan 22, 2024

Remote Worker Using a Laptop
Remote Worker Using a Laptop by Christina Morillo

Remote work is rapidly becoming a business model for the future. If your company has never hired remote workers before, here are some expert tips to help set you up for success and protect your business too.

Determine Employment Status

First, you should decide whether or not you want to hire an employee or an independent contractor (aka freelancer). Depending on the hours involved and the job description, some state laws where the worker is located determine this status for you. If you try to claim a full-time employee is a contractor, it could be considered misclassification, exposing you to lawsuits and fines. Consult with an attorney if you’re not sure which category your worker belongs to, as this will also determine things like taxes, benefits, and paid time off.

Write a Thorough Job Description

Your job description will reflect the employment status discussed above, as well as the hours and remote status. A word of warning: workers today hate being told a job is fully remote only to find out they need to be in the office certain days of the week or travel to the company headquarters several times per year. Be upfront about any travel expectations, even if they are rare.

If you are hiring an employee and not a contractor, you can technically control the hours they work and other parameters of the job, as if they were in an office. However, most people opt for working remotely because of the freedom it gives them. A good compromise is to ask the worker to be available once a week, for example, for an online meeting or to be available by phone or email during a few normal business hours per day, assuming they live in the US.

Conduct Live Interviews Online

Ideally, you want to conduct live interviews with your top candidates. This is easily done nowadays using Zoom or Skype. If you’re hiring globally, try to pick an hour that works for everyone, given different time zones. Keep in mind that if you will need your worker to be available during specific US work hours, it may not work well to hire someone on the other side of the planet.

Screen for Trustworthiness and Responsibility

Once you’ve looked at résumés and whittled down your candidates, you should start looking at soft skills, like communication and relationship building. Another key skill is the ability to work independently without a manager nearby. This requires good time management and commitment to the job.

Perform Reference and Background Checks

Whenever possible, conduct a background check on the potential worker, especially if they’re located in the United States. If they’re outside the US, check references carefully, particularly if they will be doing anything involving finances, customer data, or proprietary information. Understand that you will have little legal recourse if an employee outside the country steals data or money from you.

Consider a Trial Period

It’s smart to offer a probationary period for both of you to see if you’re a good fit. You may not be happy with the worker’s performance, and having an understanding from the start helps avoid misunderstandings that could lead to wrongful termination claims. Be sure to put all this in writing for your protection; a concise work agreement is essential when hiring remotely.

Check In Periodically

Arrange for times to catch up occasionally, whether via video chat, phone, or email. This lets both you and your worker discuss any problems and also helps the worker feel more like part of your business.

Provide the Proper Equipment

Ideally, you want to offer any employees (and sometimes contractors) the equipment they need to perform their job without compromising business information or customer data. You may need to provide things like a laptop or phone that the worker should use solely for business.

Do not send the worker money to purchase their own equipment, as this opens the door to your business being scammed. If you do not plan to provide equipment, have a written bring-you-own-device (BYOD) policy outlining how business information is to be handled securely.

Make Sure Your Business Insurance Covers Remote Workers

Finally, you will still likely need business insurance for remote workers. This includes:

  • Cyber insurance in case of ID theft, hacking, or data loss
  • Commercial auto coverage if the worker is using a personal vehicle for business purposes
  • Property insurance for any company equipment sent to the worker
  • General liability insurance in the event your business causes harm to someone else
  • Workers compensation for employees in case they are hurt on the job

The independent agents at Erik L. Anderson Insurance Agency can customize a business insurance policy for your company, including for any remote workers you take on.

Call us at 410-686-5400 today, or request a business insurance quote online now.



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