Creating High-Performance Virtual Teams of Freelancers and Contractors

Jun 24, 2014
12 Min Read

Plenty has been written about telecommuting for employees: how to encourage productivity, build a sense of “we’re all in this together,” and the logistics (such as tools and business processes) that streamline a telework lifestyle.

But what about when your team is neither employees nor on-site? That gives any project manager extra challenges.

There really are differences. Co-located employees begin with a premise of “We’re all in this together.” In contrast, virtual team members don’t natively feel, “This is my project, and thus I’m motivated to make it succeed,” and it’s rare for independent workers to have the same tools or tech infrastructure.

In this article, I highlight the special problems faced by project managers when they need to make virtual teams work, composed only of freelancers and contractors.

Make everyone’s role clear

Much depends on how you see your relationship with the freelancer or contractor, says Alan Zeichick, president of Camden Associates, a technology analyst firm, who makes a distinction between the two roles. “If it's a ‘I've got a piece of work to dole out, who wants it’ situation, then freelancing is perfect,” he says. “The only relationship you want is between you and the freelancer; it's a hub-and-spoke model. Everything is a transaction between you and the freelancer.” With freelancers, you hire someone who can do a job, get it done, rinse and repeat. If the freelancer doesn’t work out for a single assignment, you move on.

Think contractor if you are trying to build a virtual team that will stick around and span multiple pieces of work, says Zeichick. “Even if you are still engaging people officially per small project, you want to build esprit de corps, and a sense of loyalty and involvement from the contractors – and from you.”

As team leader, you may know this already. But do the people with whom you’ll be working? It’s your responsibility to be clear about the relationship expectations.

Make sure that the people who contribute are capable of working independently, which means extra attention during the “hiring” process. “If you don't have self-motivated, conscientious remote workers, you have to make up for that with more detailed processes and systems,” advises Michael Sherrill, partner at IT firm Concept32. “With off-site workers, you need to choose your battles. Don't expect them to be flag bearers for your company culture, but do expect them to perform and deliver professionally according to the standards you define.”

Which means, of course, that you have to define and document those standards and expectations.

Establish a process of frequent, transparent communication

For any virtual team, communication is the biggest challenge, especially when team members work in their own little silos on different parts of the project.

“It’s unlikely that I’m going to pick up the phone (or hit the Skype call button) to discuss every little question or idea with a colleague, when in an office it would be a quick ‘driveby’ or hallway conversation,” says Stephanie Schwab, founder and CEO of Crackerjack Marketing, a virtual marketing agency based in Yonkers NY, with staff around the world. “But that means that we’re often making longer lists that we have to cover with each other, or (horrors!) sending more emails.”

Most successful teams institute a regular meeting schedule, separating the “big picture” and brainstorming meetings from the daily-progress calls. “We’ve recently implemented 15-minute daily ‘standup’ calls (via Skype) with myself and our Director of Client Services,” says Schwab, along with 30-minute weekly internal client team meetings. In addition to ensuring the team is in sync on goals and tasks, it also helps team members to connect personally, she says. It works the same way that water cooler chat works in an office, “but without completely interrupting our workdays at random.”

When David Bradbury started his latest venture, with no employees, “I brought the team of virtual freelancers together weekly using Google hangouts. This meeting delivered two outcomes: We all agreed on the workflow for the coming week, and it created a shared sense of responsibility for delivering the week’s sprint.”

When you build a team made of contractors, communication needs to go beyond hub-and-spoke. You want them to bond both with each other and with you. “You want your contractors to know each other, have a relationship with each other,” says Zeichick. “Social media is a new way of doing this, of course; something like Yammer could help, or a closed Facebook group. Perhaps occasional conference calls, brainstorming sessions. If you are local to the geography, get together for coffee or lunch in a group.”

Track work items ruthlessly, with regular deliverables

When your team members are too far away for you to look over their shoulders, and as contractors they likely have other demands on their time, you have to pay even more attention to tracking progress. “The biggest problem I've encountered is that not everyone understands how to manage their time and their actions,” says Johanna Rothman, consultant at Rothman Consulting Group. “Where is this project on their never-ending list of projects? I like monthly deliverables (at the very least), so everyone can see what's going on.”

The deliverables schedule varies based on your project. The important part is that you as team lead can tell immediately if things are getting off track. “I don't care so much what tool we use, as long as we have small work items,” says Rothman.

That’s why it’s important for you to hire people who can work independently and communicate easily. “What you need are people who see the value of being part of a team – even if they are only being paid for ‘work product,’ such as code delivered or photographs accepted or articles published,” says Zeichick. “You want to invest the time in helping them see the big picture of what you are trying to do, and including them in that vision.”

Create shared workbenches

The process and attitude matters more than tools, but tools do make a difference. Most use some form of constant communication (persistent chat rooms such as Hipchat, instant messaging, or old-fashioned Internet Relay Chat), video- or audio-conferencing (such as Google Hangouts), and project tracking tools that identify the work to be done and who’s working on it.  (We’d be remiss if we did not mention Intuit Quickbase here). This isn’t meant to be a roundup of collaboration tools and tracking software – you can find several of those on your own – but do take the time to investigate which software works with your company’s infrastructure and for your team members.

Whichever tool you pick, be sure it addresses the almost-inevitable issue of time zone incompatibility. Look for ways to stay in touch that can be accomplished on varying schedules. As wonderful as it is to use videoconferencing, it’s not a long-term solution if it means some team members have to get up at 3:00am on a regular basis.

It starts and ends with trust

As with all successful teams, it’s important to build a team that trusts one another – and you. Even if they aren’t employees, everyone cares about doing his job well, and being appreciated for his contributions.

Dann Berg, co-founder of TripExpert, says he made a point of asking his contractors for their opinions in order to make each of them a valuable part of the team. “Asking for feedback for things like design, user experience, and the overall direction of the website proved tremendously helpful,” he says. “We ended up with a better product, and the staff became more attached to the work and success of the website. At the end of the day, decisions were in the hands of the managers, but it was the group effort that made the company, and the process, even better.”

But don’t assume that remote workers have the same business culture you do. David Bradbury spent 12 months creating his credit card selection site with people in Poland, Indonesia, Australia, and the Philippines. Trust evolves differently in virtual teams, he says. In a traditional office, colleagues develop relationships and trust through social interaction and collaborative work. “Across a virtual team, colleagues develop trust very differently through reliability, consistency, and responsiveness –which the HR folk have christened ability-based, or task-based trust.”

When it works, this is an ideal way to run a business. “Four years in, I can’t imagine running my agency any other way but virtually,” says Schwab.

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