The Top Five Questions You Need to Ask Before Hiring a Virtual Employee

The Top Five Questions You Need to Ask Before Hiring a Virtual Employee

Felicia Sullivan

The future of work is remote work.

Gone are the days when everyone punched timecards and clocked in. In those days, managers would dedicate part of their day to monitoring employee attendance, while employees wasted productive hours making sure they were accounted for.

“Face time” wasn’t an application on your phone; rather, it was a way in which you pledged loyalty to a biweekly paycheck. “Be seen and accounted for” was the mantra before digital and cloud technology, before remote work was considered more than just the random slacker employee tapping away at their computer in their pajamas. Now, technology has made it easier to work from home while keeping tapped in to what’s going on at work.

The Growth of Flexible Work

According to a study jointly sponsored by Global Workplace Analytics and FlexJobs, the number of telecommuting workers (not including the self-employed) in the U.S. has skyrocketed by 115% in the past decade, and 40% more employers have offered flexible work options over the past five years.

Telecommuting isn’t reserved solely for the younger, tech-savvy generation — the average age of a virtual employee is 46 and the industries span forestry and farming to social services, healthcare, and administrative, financial, and legal services. In fact, five of the fastest-growing remote work categories in 2017 were therapy (including social workers, rehab coordinators, and occupational therapists), virtual admins, client and customer services, tutoring, and state/local government office jobs.

Cost Savings Both for Employer and Employee

Virtual staffing has been a boon for small businesses. If workers in the U.S. worked half of their time at home, the national savings would be over $700 billion a year, according to analysis by Global Workplace Analytics. Businesses could save $500 billion in rent, utilities, absenteeism, janitorial services, equipment, supplies, and lost productivity — more than a whopping $11,000 per employee per year. Nothing says bottom-line bliss like cost savings — generating dollars that can be reinvested in your business.

Employees also win big by saving on commuting costs that give them back both hours and dollars daily. Remote working has provided a financial lifeline for parents who need flexible schedules, the disabled, and talented staff who can’t find the right work locally. Happy employees are productive ones.

Five Interview Questions to Ask

If you have the kind of business where schedule flexibility — anywhere from offering employees one day a week to work from home, to working completely remotely — makes sense, here are the five questions to ask when interviewing potential candidates. These questions will give you a better sense of the person you’re interviewing, and if they have the right discipline, experience, and organizational smarts to work virtually.

1. Have they ever worked offsite, in any capacity, during their career?

You want to know if they understand the difference between the occasional WFH day and operating their own virtual office. You don’t want your virtual employees to be slackers, but you also don’t want them burnt out and running on empty.

If they haven’t actually worked remotely, you can ask them how they’ve managed a work-from-home day.

2. If they have extensive remote experience, ask them how they’ve structured their day.

The candidate’s response to this question will determine whether they’ve actually done this before and have a plan, at the ready, to structure and organize their tasks over the course of a day. Do they have a project management system (anything from using a simple word document to create their daily to-do list, to free software tools like Trello and Asana) to prioritize urgent tasks and get the job done?

  • Are they able to organize their day such that they can manage team interactions, calls, and meetings with blocks of time needed for “thinking” work?
  • How do they keep themselves accountable for the big things that need to get done while making sure the day-to-day work doesn’t fall through the cracks?
  • How do they keep connected with team members for motivation, idea-sharing, and human connection?

3. How often did they receive feedback on their work, and what has that experience been like?

Here, you want to learn how they’ve grown in their roles. In person,
it’s easy to pull an employee aside and give them on-the-job feedback; however, remote work may give you less access to your employees face-to-face.

If, instead, you could be relying on something closer to virtual performance reviews, you’ll want assurances that the candidate has taken feedback and has grown as a result.

  • How have they managed personal and professional growth at a distance?
  • Are they a solid communicator and connector?
  • Most importantly, how have they been able to structure a plan to take their performance to the next level?

4. Ask for an example of when they took the virtual lead on a project or played a major role in one.

Was the project assigned to them or did they volunteer for it? Have them tell you how they followed their project to completion and any real challenges they faced along the way. This will signal whether your candidate is a motivated self-starter or someone who needs to be managed.

5. Give them a real situation from your business where an urgent request came to the team.

Ask the candidate how they would manage urgent requests and find solutions virtually. Here, you’re looking for creativity, agility, and someone who can get the job done regardless of location, location, location.

Digital technology has transformed clock-watchers into productive staff. Telecommuting provides employers with a greater talent pool and incredible operational and fixed costs savings. If virtual work makes sense for your business — whether it’s days worked from home or having completely remote staff — arm yourself with the right questions to determine if your future employee can get the job done without punching into a clock.

14 Responses to "The Top Five Questions You Need to Ask Before Hiring a Virtual Employee"
    • Lisa Melchior | August 2, 2022 at 12:40 pm

      Great questions. I would like to see more articles about managing virtual employees in the future.

      • Small Biz Ahead | August 2, 2022 at 3:30 pm

        That’s a great topic, Lisa! We can definitely work on creating articles around that. Thanks for commenting!

    • Haynel Rose | August 11, 2021 at 1:06 pm

      6. Can they be responsible for Tools, Access and Security for company data.

      7. Effective collaboration with teamates in a timely manner to solve problems and be engaged.

      8. Dealing with Teammates if in different time zones.

      • Small Biz Ahead | August 12, 2021 at 11:29 am

        These are definitely good interview questions/topics! Thank you for sharing!

    • Cher Zavik | August 11, 2021 at 10:37 am

      Great insight for virtual managers.

      • Small Biz Ahead | August 11, 2021 at 2:46 pm

        Thank you for the nice comment! We’re glad you found our article helpful.

    • Rosemarie Gattuso | August 11, 2021 at 8:47 am

      Not only did the 5 question lead to hiring virtual staff help, but it also can help the hiring individual reading it to link their way of thinking through any additional questions geared toward the remote work process.

    • sharon M | August 11, 2021 at 7:04 am

      Thank you! Helpful!

      • Small Biz Ahead | August 11, 2021 at 2:49 pm

        You’re welcome, Sharon!

    • K. Taylor | August 10, 2021 at 10:41 pm

      How are VA’s and the employers taxed?

      • Small Biz Ahead | August 25, 2021 at 1:59 pm

        Same as regular employees. Be careful about state taxes though – talk to your accountant about what you may need to withhold.

      • Joe Beverly | August 3, 2022 at 9:48 am

        I’m biased (since I’m the president of Corporate Payroll Services), but you can also speak with a payroll processing company. Any good payroll company should be able to handle taxes in any state or locality.

    • Jean Orth | August 10, 2021 at 1:17 pm

      Thank you

      • Small Biz Ahead | August 10, 2021 at 2:56 pm

        You’re welcome!

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