How to hire telecommuters: 7 must-ask questions

Hiring remote workers can be tricky business. Here are some questions you should ask would-be telecommuting employees -- and some red flags to look for in the answers.


For employees, it's easy to enumerate the advantages of working remotely, such as flexibility, work/life balance, and avoiding an hour-long commute in highway traffic. Employers have grown to appreciate the advantages of hiring telecommuters, too, whether as full-time telework staff or as colleagues on geographically diverse teams. And companies offering telework programs have employees who are more productive and happier.

But finding someone who is technically qualified for the job, a good team fit, and suitable to work remotely adds another level of complexity to the hiring process.

Too bad that most of us aren't sure exactly what to ask.

Some of these issues are hard to address since most of us share a tacit understanding that what really matters in a job interview is Can this person do the job? and not Who are you when you are home? Yet from the viewpoint of someone looking to hire a dependable employee, it's important to know a telecommuter's work environment and situation. He will, after all, be bringing his home life to work with him.

Plus, in any circumstance, hiring someone is about deciding, "Whom can I trust?" You are betting your department or even the company on the employee's abilities and dedication. It's hard enough to tell if an employee is trustworthy when she is sitting in front of you. When the worker is outside your direct observation, the issue of trust is even more important; several people I spoke with cited times when remote workers didn't deliver, or at least they didn't seem like they were working to deliver. (It was impossible to tell the difference, which is sort of the point.) Trusting a stranger with your company's success (the "one day at a time" success) without knowing if his butt is actually in the chair is even more fraught with difficulty -- especially if you were burned once.

The following questions will help you hire the right would-be telecommuter.

Have you ever telecommuted before?

This is a biggie, because telecommuting is different from working in an office. Someone who has never done it can't know for sure whether she's suited for these differences. Working remotely requires a comfort with solitude and a respect for deadlines that many people lack.

Even if this applicant is perfect for the job and ready to make the transitions and tradeoffs necessary for happy telecommuting work (17 of which I wrote about a few years ago), the point is that she does need that adjustment period. You run a danger that the new employee is great at her assigned tasks (best sysadmin ever!) but soon learns that she hates to be alone in the house all day. Then what can you do?

Yahoo telecommutingImage credit: ITworld/Phil Johnson
For Yahoos, neither working at home nor pants are optional any more

I'm not suggesting that you reject someone based on a lack of telecommuting experience. But you should be especially attentive to her answers. Ask as a follow-up, "What adjustments do you expect to make in your work routines?" Look for someone who has thought through the changes. If someone hasn't considered anything more than, "I would not have to commute! I hate to drive!" it's a bad sign.

If the job applicant has telecommuted, the follow-up questions should be, "What worked well in that situation? What could have been improved?" Even if you don't end up hiring this individual, you might gain insights that can inform your company's telecommuting policies or improve your own management skills.

Tell me about your (home) work environment.

catsImage credit: ITworld/Esther Schindler
Telecommuters need to put special attention on establishing relationships with their coworkers. The author's cats Meriwether and Shaka demonstrate.

Most successful telecommuters I've known have a separate workspace, often with a door that closes. If the job applicant says he works on the kitchen table or from a local coffee shop, it's not a kiss-of-death, but it's not a great sign, either.

The exception, I think, is when the individual is a long-term telecommuter. One reason to ask about the dedicated home office is that many of us need to make a physical distinction between "I am at work" and "I am at home." Some successful telecommuters no longer need a physical doorway to divide their work-time and personal-time.

Still, pay attention to more than the "I have an office" answers. What's their Internet connection setup? Do they own a suitable computer, telephone, etc.? The issue of who-supplies-what-equipment presumably will be dealt with later in the selection process, but certainly it's reassuring to know that the home office is a home office.

It's also an opportunity to learn more about the person and what's important to him -- at work and beyond. For example, the work environment discussion may also raise dog and cat ownership. Speaking for myself, I can't imagine working without a cat on my lap, and it's among the reasons I can't fathom working in a "regular" office again. Anyone who asks about my home office setup will be told about my personal muses.

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