10 hard telecommuting questions to ask remote workers

As telecommuting becomes ever more accepted, more of your employees will drop hints that they too would like the option to sometimes work from home—in fact, in a strong job-seeker’s market, some prospective hires might even assume that’ll be part of the conversation from the beginning.

Before you agree to any telecommuting arrangement, sit down with the employee and go over the basic ground rules, but then dig deeper. When a separation is created between worker and office, there can be many side effects that go along with the perceived benefits. To avoid unpleasant surprises, ask these 10 questions.

On their productivity

1. “What are the ‘distractions’ you’ll be avoiding?” Telecommuters generally argue that office life brings on a variety of distractions that impede their productivity. It’s important to investigate what those are. For example, if co-workers are a “distraction,” why is that, and what constitutes an unnecessary interruption?

Say a co-worker has a valid question or update, or wants to discuss work-related matters … is that a distraction or part of the workflow, the necessary give-and-take that produces understanding and quicker results?

Often workers perceive anything that knocks them briefly out of their own flow as a negative. Make sure the so-called distractions don’t add up to someone simply not wanting to be bothered.

2. “How willing are you to jump on the phone?” We all think we’re just a phone call away from engaging with our colleagues. “Just give me a call!” we say.

Some of us, however, don’t really mean it. Emails and Slack messages are comfortable because we’re offering someone a cushion in which to respond; these make life convenient for them. Phone calls, however, represent a real-time request for attention, much in the same way the sudden office drop-in does.

Is the person requesting a telecommuting schedule someone who’s likely to pick up a ringing phone without a second thought, and likely to make a call as soon as an issue is more easily resolved with that method of contact? Or might a natural complacency, even shyness, keep problems from being addressed immediately, resulting in ever more emails and instant messages that go waiting?

3. “Are you susceptible to ‘islanding’?” One problematic result of remote work is that an employee can stop seeing the rest of the office world to its full degree.

When we work utterly on our own, there’s a natural tendency to focus intensely on our individual workload and block out everything else. Little by little, our jobs can take on an oversized importance in our minds, and the intrusion of others’ concerns can seem more aggravating. If you don’t talk to people in the break room each day or sit with them in meetings often, it becomes very easy to forget how important their own stakes are.

Get a handle on the employee’s awareness of and interest in what goes on outside their own sphere. Make sure they’re not looking for an excuse to essentially disappear and cut themselves off.

4. “In what ways will you be better? In what ways will you be worse?” The second question will produce more interesting results than the first, of course. Expect to hear the usual answers: “I can be more efficient at home” and “Easing the commuting stress will help with work/life balance.” What you’re really after is an honest appraisal of someone’s self-discipline. If an employee can see no downside at all to telecommuting, they’re not quite looking at themselves or the situation closely enough.

Pinpoint at least one specific potential problem issue so you and the employee can address it together right now.

On their contentment

5. “Are you okay with the fact that telecommuting could end?” Working remotely is a powerful benefit—the kind that people get used to quickly and don’t ever want to give up. But you must make it clear that nothing is forever if the perceived results aren’t quite what you’d hoped for. And ultimately, it might be difficult to put your finger on just why you’re not happy with those results.

An employee, for example, may produce just as much, if not more, than they did before, yet you feel communication among the team is suffering, or the culture is breaking down. In this case, you might find the employee becomes greatly put out by no longer being able to telecommute. After all, they didn’t do anything wrong.

Everyone will say they understand that the benefit might not be permanent, but few will let it roll off their backs if this amazing convenience is pulled away.

6. “Are you okay with not being a ‘full part’ of the culture?” The office is far more than a place to show up and work. It’s also a place where connections are made, lives are shared and a community is grown. Going without that can be an energy-sapper and create the sense of being always on the outside, looking in.

Is the employee used to not having co-workers around whose energy can be stimulating? And can the office itself withstand an environment where many people feel only tangentially connected to the culture?

7. “Would you object to digital monitoring?” We’re not talking here necessarily about video cameras and ankle bracelets. I.T. has more subtle ways to check in on remote workers, even with something as simple as compiling log-in and log-out times. And perhaps you as a manager will find yourself sending a few more emails and making a few more calls to a telecommuter than normal. At what point might that begin to seem like de facto monitoring?

Here, the danger is in creating a trust disparity between remote workers and those in the office. If you keep tabs on one group, why not the other? Ask an employee how they feel about monitoring even if you don’t intend to do it currently—you never know if things will change, especially as technology develops and makes it easier and less intrusive.

On cold reality

8. “How reachable do you plan to be?” To avoid causing frustrations, a remote worker must adopt a response method that satisfies everyone.

Find out if the employee intends to work a very regular schedule, including meal breaks that correspond to everyone else’s, or wants to play it looser. Don’t demand a response time that’s faster than normal, but do make it clear that when someone in the office tries to reach a telecommuter and isn’t immediately successful, a mental clock begins to tick a little faster than normal, unfair as that may seem.

9. “Do you know when not to work?” There are workers who excel at home to such a degree that they find it difficult to stop producing. Once set up with the tech they need to work from anywhere, anytime, they bring nights, weekends and holidays into play, potentially without you realizing it.

If you’re dealing with a nonexempt employee, overtime rules could easily be broken, and that could come back to haunt you. Make sure they understand what time is countable and payable. Do they realize what constitutes unpaid de minimis time?

Even if a salaried employee is exempt from such considerations, remind them of the potential burnout that can happen if they work themselves too hard. When certain personality types no longer have an off switch, they can do amazing things—it’s your job as a manager to know when it’s coming at a price.

10. “Do you know the misperceptions that are created by telecommuting?” When a staff is divided between telecommuters and those who come in every day, it’s difficult for the efforts of those working at home to be as visible. They’re not there as often to talk about that work, they’re not seen walking through the hallways with papers in their hands, they miss meetings and informal huddles. And when the inevitable nitpicking of someone’s efforts happens, naysayers often fall back on the first line of criticism: “They’re not here.”

Frustrations can mount. Petty jealousies can grow over perceived benefits; after all, why can’t everyone work from home? Be sure your employee understands that a telecommuter can risk becoming the victim of certain misperceptions.