As a youngster, I enjoyed reading mystery novels such as the Nancy Drew or the Hardy Boys books -- and gained an appreciation for sleuthing in the process. In my adult life, I've put that to good use when it comes to business.

The hiring process is never easy, especially when you're taking on remote employees, but being a good sleuth and sniffing out clues (where legally permissible to do so) will save many headaches down the line. Over the years, I've hired a number of remote employees for my various businesses with different levels of success and learned a thing or two in the process.

First of all, considering remote employees is a good idea. Employees who work from home are found to be generally happier and more productive. It's no surprise that allowing employees to work from home will save you money on expensive office space.

However, there's just one catch: human nature. If you're a business owner, then "remote worker" triggers another concern: that you're paying someone your hard-earned money to sit around to watch Game of Thrones. 

Interviewing potential virtual employees is tricky enough. Here are some questions I've found that help to get a better read on a prospective work-from-home employee:

1. Are you clear on the expectations for this role? 

If your job description is something vague such as "improve our sales performance" or "foster better communications across the organization," then it's easier for people to goof off all day because the position lacks clear, ascertainable criteria for performance. But if it's "cold call 100 prospects per day, log them in the company tool, and produce at least 20 solid leads per week," then you'll know in a week or so if your new employee is doing his job.

I have found being highly specific about what is required can set both parties up for success. It's OK to communicate to your interviewee that until trust is earned it has to be quantified.

2. What motivates you? 

You're looking for a self-starter, because people who are looking to be told what to do won't do well in a work-from-home situation. Given the many temptations of a home office, a high level of motivation is imperative. This is where figuring out how the person thinks is important. I prefer to get at what makes a person tick and have had great success with good hires the more I do this.

Hunt for clues that are keys to assessing the degree of motivation the person has, such as whether the person has started anything on their own, even if it's a neighborhood cleanup committee.

Is the person motivated to get things done and make progress in life? What's driving your would-be employee? Is he supporting an expensive hobby? Does she want to learn the ropes so she can open her own business someday? Finding the source of motivation should be your main goal for the interview.

3. Have you done this before? 

Your interviewee either has or hasn't. If not, then the person would be trying this out on your dime, so some scrutiny is required. If the person has, then you need to know what happened. If the earlier work-from-home situation fell apart for reasons beyond your interviewee's control, then check the story out with the previous employer.

The key here is figuring out if the candidate knows how to work remotely and has done so successfully in the past, and to get that story corroborated by others. If not, proceed with caution.

4. Do you have a quiet place to work? 

Kids, dogs, and noisy neighbors can all be major distractions when a person is working from their home. If your would-be employee doesn't have a home office, then Starbucks might be an OK option -- unless he or she has to make phone calls, because nothing screams "amateur" like the sound of a coffee grinding machine in the background while someone is trying to close a deal.

Here you might want to meet the interviewee halfway by offering to foot the bill for a shared office space at a place like WeWork or Grind.

5. Are you comfortable with time alone? 

There's one major downside to working from home: social isolation. Studies have shown that the key to happiness is interaction with other people.

Someone embarking on their first work-from-home experience might soon find that the arrangement is making them miserable. Since you want a happy employee and someone who will stay around for a while, it's imperative for their sake and yours that they have a strong social support network and options such as WeWork near them where they can go to alleviate their loneliness.

Ideally, you'll get someone who has confronted this issue before and has a strategy to deal with it. This draws from my earlier strategy about knowing what makes a person tick; the more you know about them, the better you can assess whether they are a good fit for a remote work opportunity.

6. Are you an optimist? 

Obviously, don't ask this question, because you won't get a straight answer. The best way to get at how a person thinks is to present a hypothetical scenario to see how your interviewee responds.

For example, "You're going through a sales slump and no one's calling you back. What do you do?" What you're looking for here is a clue to how the prospect has handled adversity in the past. Why? Optimism is key to motivation. You can't be motivated if you think you have no chance of succeeding or have no belief that you will.

Pessimists are dead weight if you are setting up a remote workforce, so sniff out the pessimism in the interview.

In my experience, most people have a decent work ethic and are motivated to make their remote situation work well for them and their employer. There is, however, a large percentage of the population who need to be in the office, requiring regular motivation and direction.  

Ideally, you'll have a mix of both, but the important thing is that your employees are happy. In the best-case scenario, both you and your self-motivated, optimistic, emotionally solid employee will be thrilled about a remote employment situation.

Sizing up a remote employee is one area in which you don't want to dial it in, because it's to your benefit to channel your inner Nancy Drew and pick up on the clues through thoughtful interview strategies.  

Published on: Jan 10, 2018