Virtual Help: How to Hire Someone Online and Make It Work

Arguably, one of the most interesting developments the internet has brought us is the ability to work remotely. Our offices can be wherever we are, but, even more dramatically, it's now possible to work and collaborate with people you might never have had access to in the past.

The cost savings can be dramatic: Instead of hiring a full-time writer, who will need office space, a telephone, internet access and benefits, a lot of employers outsource their writing tasks to freelancers, like yours truly. In turn, businesses like mine can take advantage of a global pool of talent to do everything from bookkeeping to virtual assistant work, at a fraction of the cost it would normally take to hire someone in person.

Hurray for leveled playing fields!

A lot of people are curious about the way I get certain tasks done. At the risk of tipping my hand, I admit this: There is no way my business would be viable without the help I get from virtual employees.

In addition to the success and luck that I've had, I've also had arrangements which haven't worked out so well. Based on this experience, both as a service provider and as a manager (I also touched base with my superstar transcriptionist to get her two cents as well), I think it's possible to hammer out a few need-to-know items for anyone seriously interested in outsourcing their work this way.

To get even more pointers (because I know I could use a few, myself) we also talked to oDesk vice president of market post operations, Matt Cooper, to get his advice as well. (Note: oDesk is a service that connects and provides a working platform for distance contractors and would-be employers. Elance is another.)


First, know what you want to accomplish. Have very definite goals, tasks and outcomes in mind, and written down, if only for yourself, before approaching someone to have the work completed for you. Even if you think you want to hire a project manager to do this for you, it's necessary to have a definite picture of what you want that project manager to accomplish.


When hiring, Cooper says even when using a service like oDesk or Elance, it's necessary to look at the contractor's work history and interview to assess a contractor's personal characteristics, motivations, skills and knowledge, just as you would when hiring in person. When using a service like oDesk, do not simply rely on ratings. (In my experience, many service providers, particularly those overseas, will demand a high rating, whether they deserve it or not.)

"Just because they were a five star worker for someone else's project, doesn't mean they're going to be a five star for yours," Cooper agrees. "Ratings, feedback, their work history, hourly rates, the jobs they apply for, their LinkedIn profile and their non oDesk resume are all factors to consider."


Use video during this process, or at least pick up the telephone, and work to develop a relationship. "One tip we push pretty aggressively is the use of video. I mean, Skype's free. If you're trying to build a long-term working relationship, nothing beats a face-to-face conversation."


Start with a test project. "Consider hiring multiple people for the test project, then select the contractor whose performance best meets your needs before moving ahead," he says. "If you hire three people for a test project and end up keeping only one for the long term, you're still going to save a lot of money."

Personally, this is one practice I commit to for each hire. It works well. As part of this too, try not to be too bent on getting the best possible price.

One oDesk service provider I work with regularly is Lisa Kmetz. Her thoughts on best price seeking are pretty spot-on: "Some clients will hire based on rate, as they are looking to pay cheap, but in the long run they end up spending more because the work they receive isn't up to par and they end up hiring someone else to redo it."


Focus on over-communicating. Be very clear about your requirements and expectations. When using overseas help too, or anyone else for that matter, don't assume pages of written detail will get you the results you need – people learn, utilize and assimilate information in very different ways.


Be a manager. Remote, virtual or otherwise, contractors often need managers who check in periodically to find out how the work is going, instead of simply "throwing work over the wall," and walking away, expecting to get great quality work back at the end.

This urge to throw work over the wall, so to speak, is very tempting. It's the way I tend to work with a lot of my own clients, and there is the assumption that if such arrangements don't work out, there are always other contractors. My friends, this is a mistake. Learn from it. Even if you think you dislike micro-management, you'll need a little bit of this, especially in the beginning.

"Once you've been working with the person for six months, they can probably read your mind, but in that first interaction, that's usually not the case. It's better to over-communicate, provide well defined milestones, and be very specific, rather than risk not getting what you're looking for," says Cooper.

"This is just management 101. If you're not a good manager face-to face, you're going to be a worse manager remotely. There are management challenges in general that are somewhat exacerbated when the person's not sitting next to you every day. You need to be much more deliberate in how you go about managing a virtual workforce – people who are not well organized to begin with are going to have a steeper learning curve."


Kate McCaffery is a freelance writer, editor and former urbanite, now living somewhere in between the lake, the ski hill and some farmer's cow path. mccaffery.ca/kate2.0/ for more information.

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