The Way We Work

It’s no longer difficult to find good remote contractors, but even easier than finding a new contractor is building trust and rapport with one you already know. Any competent contractor should follow your instructions, stick to budget and meet deadline — so how do you identify the potential star that you should invest in an ongoing relationship with?

“In my mind, there are three things that differentiate great contractors,” says Tom Rupsis, an employer and IT consultant in Billings, Montana, who relies on oDesk programmers to help him deliver anything a client needs, quickly and affordably. “First, the best contractors have great communication skills. … The second thing is their ability to get me to the best solution. … The final thing that really stands out to me is a contractor who strives to know the business side of whatever we’re working on.”

If you put those three things together, you come up with a contractor who works to understand his client’s needs beyond merely completing the task at hand, and who puts that employer’s satisfaction first. NetSuite programmer Clemen Canaria says that sometimes means telling a client how to pay him less.

“If a task will need a skill that is not my forte, and I have only a little background on it, I tell the client that it may be best to have someone else do that specific task, as it would take less time and less money,” says Canaria, who is based in the Philippines. “It’s my way of earning my clients’ trust, thus earning a long-term working relationship with them.”

Top-Tier Communication

Bad communication can really take a toll on a remote collaboration. But Rupsis, whose Granite Peak Systems consultancy has employed experts from India, Bolivia and the Philippines, emphasizes that communication is much more than native-level language skills.

“I don’t mean that they have to speak perfect English. I mean that they keep me informed on their progress without me having to ask what’s going on,” he says. “The best contractors ask questions for clarification instead of making assumptions about what I need. And they document their work sufficiently that other contractors could take over if necessary.”

“Clients are very cautious about communication,” Canaria agrees. “I always follow up on them, making sure I give updates and prompt replies to their emails.”

Rupsis says that constant availability isn’t what he’s looking for; he counts on a contractor to manage his expectations, and then meet them. “If I know you do most of your work on the weekends,” he says, “then I won’t think about it during the week and will watch for updates over the weekend.”

An Eye for Innovation

Canaria says that once he has an understanding of his employer’s goals, he’s quick to offer better ways to either enhance the front-end experience or make back-end maintenance simpler.

Clemen Canaria, contractor

Clemen Canaria, contractor

“I suggest solutions that I think would make their account setup better and more intuitive for their users,” he says.


Rupsis says this is exactly the approach he looks for.

“When I hire someone, I’m saying that I don’t have the skills necessary to do a job,” says Rupsis, who used oDesk contractors to create and market an online application for staff scheduling, Schedappy. “I need their technical guidance on the best way to implement the solution. The best contractors will say, ‘There are a couple different options here. You could do X, Y or Z. I recommend Y because…’”

The Holistic View

Rupsis says the contractors he turns to again and again think beyond the task to really understand the core need their work is meant to address.

“Just about every successful contractor I’ve hired has very quickly acquired that understanding of what we’re trying to do from a business perspective,” Rupsis says. “They started asking clarifying questions early on that showed a synthesis of the business process with the technical requirements.”

He says he spends a lot of time educating new contractors on the business model and processes involved, and says that deeper understanding of a client’s needs and his own expectations pays off.

“When they can take that background and apply it to whatever aspect of the project they’re working on,” he says, “then we end up with better solutions for our clients.”

And a Little Follow-Through

Canaria adds that a top-notch contractor excels from start to finish, and that means a final check-in.

“I make sure that they are happy with my work by following up or checking up on them once I submitted the output,” he says.

It’s that kind of holistic perspective and initiative that Canaria and Rupsis say makes for the best long-term work relationships.

If you’ve got thoughts on building successful long-term work relationships, please share them in the comments!

Brian McDonough

Freelance Writer

Brian McDonough has been a writer and editor for more than 15 years, and has managed teams of in-house and freelance writers for newspapers, magazines and web sites.