How to hire telecommuters: 7 must-ask questions

Is this what you think of when you hear the word 'telecommute'? It doesn't have to be that way. Credit: Image credit: flickr/fogcat5

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.

How comfortable are you with troubleshooting connectivity?

The work environment discussion should also include questions about the job applicant's ability to act as her own IT person -- especially if you're hiring for a non-tech position, but plenty of software professionals are lost when it comes to networking, too. If the individual is clueless about hardware, it creates implications about needing to send a tech to the house or having to send a laptop to-and-from the home office overnight.

As a follow-up, ask, "If your Internet quit working, what would you do?" There's a world of difference between the answers, "I'd wait for my wife to get home; she's the geek here" and "I'd hack the router to try to figure things out before I call the cable company about the outage." It doesn't hurt if the applicant mentions that the local library has free Wi-Fi access. That demonstrates a desire to keep working during Internet outages and self-sufficiency that goes beyond network or laptop fixit skills.

Tell me about your daily work rituals.

Or, How do you structure your day? Successful teleworkers often establish a regular routine for getting work done. It may represent their own skill sets (e.g., "I do e-mail before breakfast, make phone calls after lunch; my best concentrated work happens late in the day"), time-of-day preferences (morning person vs. night person), or scheduling needs ("I take the kids to school at 8 a.m., do four or five solid hours of coding before I pick them up at 2 p.m., and try to arrange meetings later in the afternoon"). At a minimum, it's reassuring to know the telecommuter has this kind of self-awareness and a strong sense of "work time."

There isn't a predefined "right answer" here. However, you may learn things that make this candidate a better (or worse) team fit. You already know about your company's schedule and needs (9-to-5? Lots of meetings in the early morning? We don't care when you work, as long as the work is done?); at issue is whether this person dovetails into that process. A west-coast early riser will get along better with office-based colleagues in Boston than will someone who prefers to crawl out of bed at the crack of noon. This isn't to say that people can't change their behavior; some of it may have been required by their last gig. Certainly it's fine to clarify, "We have a team meeting at 9:30 every morning; would that be a problem?"

This is also an opportunity for the applicant to obliquely offer information that might be difficult (legally at least) for a manager to ask directly. In the "I take the kids to school at 8 a.m." answer above, for example, you now know that there are children and that the applicant won't be distracted by them during key work hours.

How do you prefer to communicate with colleagues?

Since most telecommuting teams see each other in person infrequently, it's very important that everyone easily communicate with -- not just to -- one another. For example, a development team has to work out how to do code reviews remotely.

SkypeImage credit: Stephen Sauer/Shutterstock

We all have a most-comfortable way to talk with other people. Given a choice, would this person rather communicate with colleagues face-to-face, using e-mail, instant messaging, in a video conference, a telephone call, or... what?

If you're the hiring manager, consider the preferred communication style among the existing staff, as well as with the new hire. I know an office worker who is terrible, absolutely awful at e-mail; he never "hears" what you tell him in an e-mail message, though in person he's just fine. That creates strife with the mostly remote staff. Another colleague receives my e-mail message and immediately picks up the phone to talk about its contents, even if I prefer to stick with e-mail for searchable history ("When did he say that would be done?"). Again, there's no one "right answer," but it helps for people to be on the same page.

This is also the time to discuss expectations about visiting the office, whether that's once a week or quarterly or whatever. As the employer, you need to make clear who pays for trips to the office, if it involves a flight, and what might happen if there is a budget crisis. But at this point you should learn from the employee whether and how often they are willing to spend some face time, and how they expect to use that time to build relationships.

To succeed as a teleworker, you really need to have good "social" skills in email or IM or whatever the team uses that substitutes for office chit-chat. Not just for the work-a-day stuff ("the build is done, everything should work now") but for people-bonding ("ooh, what a pretty quilt!").

It's especially important to have "comfortable" communication when things aren't going smoothly. In person someone can overhear a coworker cussing at the computer. At home, nobody knows that this project has driven him to tears -- unless he tells someone about the frustration. So you one question you might ask in the interview is, "How soon do you ask for help when you are stuck? Who do you ask?"

One way to get at this issue is to ask the job candidate about a past experience: "Tell me about your experience reviewing someone else's work remotely. And someone else reviewing your work remotely? What tools did you use? How did this differ from reviews in person? What would you do differently now than you did then?"

Tell me about your remote project tracking experience.

For most hiring managers, the burning issue is how the new hire will work effectively with the rest of the team, including management. It's hard to ask someone you're interviewing about the manner in which they'll communicate their accomplishments -- realistically it's your company that sets those standards -- but you should still ask for insight in this area.

Experienced manager Robin Jeffries suggested several related questions, which touch on metrics as well as communication skills:

  • How do you keep folks aware of what you have accomplished, what you are working on, what places you might need help (or might work more effectively with someone else), where you might be able to help others?
  • How do you keep up on office gossip (rumors about project cancellation, hiring freezes, people who might be leaving, management changes -- all the things you need to know to keep from wasting time)?
  • How do you build relationships with people you don't see regularly? How will you get people to trust you, to see you as having expertise in the areas for which you should be the go-to person?
  • How do you communicate to others when you are available or interruptable and when you are not (because you are focused on a problem or picking up your kid from school). How can people best get on your queue?

What are your concerns about working for this team as a telecommuter?

Be sure to ask the telecommuter about her needs from the manager and the rest of the team. While the job applicant may be shy about bringing up the issue, the manager should ask explicitly -- and take a "no special needs" answer as a negative signal.

If your company has telecommuting policies, this is a time to bring those up. For example, some companies require work-at-home parents to have child care for children under a certain age.

It's important for the new hire to know what to expect in regard to physical resources (who pays for Internet service, for the computer, for travel). But it's also important to learn about the sensitivities of the new team member. Is it video conferencing etiquette? A concern about being the first or only telecommuter on the team? How the team's current practices would impact their ability to be successful?

Those are the questions we'd ask. What would you add?

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