Web Work 101: Telecommuting – Out of Sight Doesn't Have to Mean Out of Mind

On first glance, telecommuting is a dream gig. You get to draw a regular salary, dress in comfortable clothing (shoes optional) and come and go as you please with no one looking over your shoulder.

Ask any telecommuter for a downside, and they’ll likely start talking about the isolation. It’s more than discussing last night’s game around the water cooler. When you’re physically in the office simply doing your job, your presence is a constant reminder to the rest of your team of the value you add to the company. No virtual project management site can replace the spontaneous collaboration that happens in the hallway. And when the boss is looking for someone to play a role on a key project, odds are her first thought isn’t going to be that guy sitting 200 miles away.

So how do you sit in your pajamas all day and stay connected to your peers?

It depends on the company, and it depends on you.

It Depends on the Company

It’s not about you or your job. It’s about the culture. How much conversation typically happens in the hallways? Do folks tend to work from home in the evenings or take their work on the road? How much work is planned in advance vs. what happens spontaneously?

If you want to work for a telecommuting-friendly company, consider working for a nonprofit organization or a vendor that services nonprofits. In general, you’d be hard pressed to find an industry more conducive to non-traditional work environments than the nonprofit sector. I’ve attended a number of nonprofit conferences where I continually meet folks who, like me, work full-time for geographically-distant causes.

Of course, if you are working to provide a direct service you need to be where that service is. However, there are opportunities to work for organizations where they may be grateful to have your expertise without the overhead of having you on site. While nonprofits do traditionally pay less than comparable jobs in the for-profit world, the compensation is not as bad as you might think. And you have the warm fuzzies of working for the greater good. Check out the Nonprofit Technology Network (NTEN) for more information about working in the nonprofit technology world.

Regardless of the sector, whatever you do, don’t expect the culture to change to suit you. If your co-workers rarely log in to a project management/collaboration web site; if they never have conversations via IM or Twitter; if emails are rarely longer than 5 words; if their idea of an impromptu conference call involves a cell phone in speaker mode…they’re not going to change for you.

Last week I was visiting my office, as I do each month, and I asked my co-workers to share with me any challenges they’ve had working with a telecommuter. They expressed that they feel bad that I miss some of the casual hallway conversation, but for the most part not much is different. They IM with me just as much as they IM with each other. In fact, after over three years we’ve developed our own shorthand language that works well for SMS and IM. We use a variety of web-based tools to keep in touch and stay organized. It’s just part of our culture, regardless of where everyone is physically.

If you can’t figure out a way to comfortably work in the culture of the company even when you’re not there – without expecting anyone else to change their habits – then you may be wasting your time. Even if you are perfectly comfortable with telecommuting, have an ideal home office, and have your supervisor’s buy-in, you will probably feel frustrated and disenfranchised in the end.

It Depends on You

So you work for a progressive company that loves to communicate via instant messenger or Skype. They use web apps or VPN and nothing important happens in the office anyway. Home office here I come, right? Not so fast.

Your coworkers can’t see that you’re busy. They can’t tell when you’re in a good mood. Except for scheduled or impromptu phone calls or web conferences, you have to be comfortable showing who you are almost entirely in written communication.

There are some people who are able to comfortably write emails that aren’t too long, aren’t too short, and it’s the same as if they were standing in front of you. They make ideal telecommuters. And there are others who have difficulty coming across as they intend in writing. Those folks should stick close to the office.

Here’s something you don’t want to hear: The successful telecommuter practices Inbox Zero. That’s right, you need to make sure that every email is read and dealt with in a timely manner. You’ll need a system for quickly responding to IMs and other messages, even if it’s to say you can’t deal with it at the moment. Superior electronic organization skills are key to a telecommuter’s successful relationship with peers.

If you can’t keep up with your email and other electronic communication when you’re face-to-face with your coworkers, forget working remotely on a regular basis. You’ll have all your typical email from the outside, plus additional communication from co-workers who can no longer just shout at you from down the hall. Imagine how your coworkers would feel if they asked you a question in person and you routinely ignored them for a few hours…or a few days? Whether it’s IM, Twitter, Skype, the telephone or the inbox, you need to get on top of the communication tool that’s as readily accessible to you and your coworkers during business hours as conversation. It’s not always realistic to expect people to call you for everything.

Fellow telecommuters: any advice you’d give to someone just thinking of taking the leap?

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