Before we even think about results or what tools we should use, we should start with the core of collaboration: the group itself. What challenges prevent the group and its members from performing optimally?

One of the problems with collaboration is that when it’s done without much planning, it leads to what’s called “social loafing,” where members of a group working together exert less effort than they would if they worked alone. This phenomenon is especially apparent in  face-to-face brainstorming sessions. To avoid this tendency, here are some aspects of the group that we should work on before embarking on a collaborative project:

• Identifiability. In one study, one of the suggested causes of slacking off during group work is that individuals can hide in a crowd. To avoid this tendency, make each member of the team stand out. You can divide the tasks so that each person has his or her own individual deliverables that are easy to measure and evaluate.
• Diversity. When we form groups or committees that will work on important projects, we tend to pick the “star players” or “big thinkers.” This is especially true in large organizations that have a lot of talent and manpower to draw from. But having intelligent individuals in a group doesn’t really seem to influence its performance. Also, according to several experiments, people tend to work harder if they expect some of their colleagues to perform poorly. So it’s important to create a group with members that have varying  skills and performance abilities.
• Group size. Apart from supporting the points mentioned above, this paper from the Journal of Management shows that increased group size was related to increased social loafing. Keep group size to a minimum so that it’s easier to account for everyone’s work. The larger the group, the more each individual can hide behind its size. 37Signals suggests that a group of three is enough to start with for a software development project. Amazon is known for having two-pizza teams, which means that if two pizzas aren’t enough to feed the team, then the team is too large.
• Group cohesiveness. Several sources also indicate that increasing the group’s cohesiveness helps to avoiding social loafing. This means that the members of your group should like each other and want to work together to pursue the same goals. They don’t have to be close friends, but they should experience a feeling of unity that makes them feel that slacking off would let down the rest of the group.

In your experience, what qualities should a team have to ensure that each member performs well?

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Throughout my online career, I’ve been part of several web working teams. On most teams I am just a regular member, but there’s the rare occasion when I find myself the team leader. Like now, for example, when my former graphic design classmates asked me to lead their new studio.

Here’s the problem: we’ve never worked together before. How could we work together and have a united approach to design? What’s so unique about us? Can we figure this out even if we’re working remotely?

To address these questions, we had to figure out our team culture. But as Jason Fried of 37Signals pointed out, culture is not something you create. How do I, as the leader of the team, provide a working environment to foster the right culture? Here are some of the strategies I’m trying:

Deep Involvement

The way that I used to set up web working teams was that each member just kept to him or herself, not minding the work of others or the business as a whole. While this was good for productivity, it wasn’t a good environment for generating new ideas or making everyone feel invested in the team. They need not be involved in the daily minutiae, but they have to know the essential business processes. Getting them involved in research, planning and brainstorming sets up an environment where you can cultivate hidden or underdeveloped strengths. This also provides opportunities for new ideas, often with a fresh, external perspective on how to make the team work better.

But this doesn’t mean that you should hold virtual group meetings for every important business decision. In fact, deliberating on big decisions as a group isn’t a good idea. Those with strong personalities tend to be more expressive of their opinions, while others end up just following the herd. To get the most out of each person, talk to them individually before coming together as a group, so that everyone’s opinion is heard equally and you merely moderate or summarize their ideas.

Encourage Sharing

If your team uses collaboration or social media tools, don’t limit it to business use only. Encourage your team to share other things  – whether it’s inspiring quotes, interesting blog posts, or the odd personal photo. Although these may look like informational clutter, they create a good environment for deeper collaboration. Also, they allow you to peek at each member’s individual culture and background.

Freedom to Engage

When looking at one designer’s recent work, I asked him why his digitally rendered drawings didn’t have the detail and dynamic lines of his hand rendered ones. He said “I’m not used to starting a drawing digitally.”

“Why don’t you draw it by hand, polish it, and then digitally render it?”
“I thought you wanted me to do it this way.” he replied.

While the designer made the wrong assumption, I should have been clear about the flexibility of his workflow from the beginning. Officially giving your team the freedom to find and develop their own processes is important. Team leaders can give everyone tips on how they can do their job better, but nothing beats the strategies they come up with on their own.

Taking a cue from Google, I also encouraged my team to spend some time working on projects that they’re passionate about. To one, this was a comic strip, to another, it was his own typeface. These projects might not directly result in profitable endeavors, but it allows them to explore different ideas and gain new skills.

Postpone the mission/vision thing

It used to be that whenever I started a new venture, I always had a solid business plan written out, complete with mission and vision statements, SWOT analyses, etc. Now, I just make a mind map or a one-page overview. Here’s why: I realized that it’s rare (or impossible) to know exactly what the final result is going to be like. The same could be said about forming teams. Give your team a bit of time to play around and figure out where you want to go before officially launching anything. Only craft your working manifesto or mission statement when you’ve settled and formed a collective identity for yourselves. Even then, it should only serve as a reminder of the things you wanted to do anyway.

As for my team, I don’t know who we are — yet. But by involving them in the important aspects of the business and allowing them to engage freely in projects that move them, I’m hopeful that we’ll arrive at the definition together.

Do you work with an online team? What is your group culture like and what process did you go through to establish it?

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I was recently asked to manage a team of graphic designers, all of them fresh graduates with hardly any professional experience. Always eager to help, I accepted the opportunity, knowing that it would be challenging and educational, for both myself and the team.

I soon discovered that working with new freelancers is very different from working with my more accomplished peers. It required me to get back to basics and deal with issues that I hadn’t encountered before. Just as I had expected, there’s a whole new set of opportunities and problems that come from working with “newbies”.

The Benefits

One observable benefit to working with new freelancers is that you’ll be forced to keep things as simple as possible. It’s not a good idea to overwhelm them at the start with new tools and complex work processes. Introduce these things gradually. This will give you the opportunity to keep the work process streamlined.

Another advantage is the fresh perspective they have. This allows them to bring more innovative ideas to the table. Sometimes, getting too used to a certain process can leave us less likely to see the flaws in the way we work. If your team of newbies is perceptive enough, they can spot these flaws for you.

While there may be some benefits to working with new online freelancers, there are also many challenges. These challenges seem daunting, but fortunately there are ways to work around them.

Underdeveloped Work Habits

Usually, new web workers haven’t established efficient solo working habits. It might take a while before they get the hang of setting deadlines, boosting productivity, and motivating themselves to work well without someone looking over their shoulder all the time.

For this particular problem, writer/editor Ruth Thaler-Carter recommends setting official working guidelines. “Anytime you deal with people new to a given arena, you have to provide guidelines. Even experienced pros might need some direction to deal with a new topic or genre,” she says. Prepare a document showing the ideal work process, including the roles of each team member. This gives everyone a better idea of the scope of their own work.

It also helps to discuss all expectations from the start. This helps to get any misconceptions out in the open, allowing you to correct them early on.

Familiarity With Tools

If some members of your team aren’t tech-savvy, they might not be familiar with the communication and project management tools you use. Even if they are used to social networking tools, like Facebook and Twitter, they might be unaware of how the web is used for business.

To fix this problem, provide a list of required tools, including the reasons why they’re needed, as well as video tutorials on how to use them. Leading by example and sharing your expectations also works, as suggested by Mary Ellen Schutz, an editor. According to her, “If [they] are very skilled at what they do, just very informal in their communications, show them a better way. Be very clear in your expectations.”

Need For a Physical Office

Although this might be less common in the future, there’s also a chance that your team of new web workers will see the virtual office as “less professional” or “less real” than physical offices. This perspective can be detrimental to the team if it means they’ll take their work less seriously.

When I was leading a local group of freelance designers, many of them brought up the idea of moving to a “brick and mortar” office in order to boost their professional image. It was unnecessary at that time, because they had minimal capital and all their clients were offshore. If your team feels this way, shift their focus to the things that really will make them look more professional instead – whether it’s their quality of service or skill levels.

Sometimes, they might be looking for a physical office because of the interaction and collaboration with colleagues that physical proximity brings. If this is the case with your team, encourage them to interact with each other while brainstorming over Skype. Or, if you work with a local team, you could schedule coworking sessions at least once a month.

It may take a lot of initial hard work to turn fresh, inexperienced students into reliable professionals, but investing the time and energy to do it is worthwhile. After all, it was only a few years ago that I, too, started out just as green as they did.

Have you worked with new or inexperienced freelancers? What was your experience like?

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One of the advantages of teleworking is that there’s less opportunities for workplace gossip and personality clashes.  Most teams approach their communications very matter-of-factly.  But I find that this isn’t always the case, especially when members each have very different working styles.

When managing a team of very different people all over the globe, what can you do to keep the team, and the work, from imploding?

All expectations should be out on the table. Most conflict comes from someone’s expectations not being met.  When someone new joins the team, the project manager or the person in charge should ask them what their expectations are.  The new members should also be told what’s expected of them.  Doing this may seem corny, but it’s the only way to assure that everyone is signing up to be on the same team, working through the same processes.

Documented accountability. If the team is unclear about the deliverables that are due  and who is responsible for them, that’s a recipe for disaster.  Each person on the team should have a very defined role from the beginning – and this should be written down, along with due dates, for everyone to see.

It’s relatively easy to document everything if you’re using collaboration software or a wiki to work with your team. Basecamp from 37signals is such an example, as it allows users to schedule project milestones and see who’s responsible for them.

Communication training. Communication is the most essential factor to the success of an online team.  It’s not the quantity of the communication that matters, more like the quality.  Communication would go more smoothly and more efficiently if there’s a “communication guidelines” slide show or document that your team can refer to.

Even minor suggestions will prove to be valuable, such as suggestions on how to use Twitter effectively, or how to send fewer emails.

Give praise and criticism privately. If you’re supervising other teleworkers, it’s important to send your comments about their work in private. This is true whether you’re working with them online or offline.

Another alternative is to send a message of praise or criticism for everyone to read.  For example, you could send a message to your entire team saying “You’re all doing great!” or “You’re all sending in good work, but here are a few suggestions for everyone…”.  Doing things this way means you’re not singling anyone out.

Be careful about the seemingly unrelated messages you send on a public venue as well.  A random Tweet such as “I’m surrounded by stupid people!” can be taken as a personal insult by your team, even if you were talking about the clerks at your local grocery store.

Supervising a team doesn’t have to be difficult, especially if you make ample preparations.  If you trust the people you work with, and everyone understands the work guidelines, then there’s fewer chances for conflicts to arise.

Have you ever supervised an online team before?  What issues or problems did you encounter?  How did you work through them?

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