Why did you decide to look to China for collaborators?

There are only three ways to acquire talent. Steal people. That’s basically what you do in the world of development — there are not good Python or Java or Rails developers sitting around with nothing to do. Number two, you acquire small companies, and number three, you go overseas and either hire people or more commonly, you contract to a contract firm. We’re basically employing techniques number two and number three, number three being unique in that we’ve built our own team of developers in Sichuan province, China.

How did you meet your co-founder?

We were introduced. I was looking for a technical co-founder. He, a fairly brilliant product developer in China, was looking for a partner, so it kind of was the perfect pairing where I needed a development team and he needed access to markets and relationships. IDG-Accel really gets the credit for marrying us together and giving us the capital to build some great products.

How many other team members do you have now and where are they located?

Right now we have about 15 people in China. Nearly everyone is in China at this point because it was easy to quickly hire and get our products developed in record time. Now I’ll backfill positions here in San Francisco, but our intention is to keep the majority of our development in China.

Why build your own team of employees rather than use contractors?

I don’t have any particular issues with contracting. I’ve hired contracting firms in the past. The challenge is, particularly when you’re developing sensitive software like security software, we need people that are committed to our product. With a contract firm you just never know what’s going to happen. You don’t have the ability to incentivize people to stay on a product. Generally, the contract firms don’t guarantee anybody on the team. So frankly we wanted the control that would allow us to build a team that could gel together, build a relationship and be committed.

One nice thing about having such a committed team in Chengdu is that while there’s a lot of burgeoning companies in China, there’s not nearly as many as in Silicon Valley, so I don’t have to worry about my developers getting poached by other software startups in the area. It can and will happen, of course, but not nearly at the rate it happens in Silicon Valley.

What other advantages are there to having a remote, cross-cultural team?

As much as I’ve always been impressed by developers in Silicon Valley, I’m thoroughly impressed with Chinese engineers’ level of commitment and willingness to work very difficult hours and perform superhuman feats. I did not expect to see the level of results I’ve seen and I can’t possibly overstate how dedicated and hungry these young Chinese engineers are to prove themselves and build great products.

What tools do you use to stay in touch and collaborate?

I wish I could say that we had some kind of special tricks and tools. The truth is, aside from the scrum methodology that many startups use to have people standing in a room for a couple of minutes reviewing a project, most teams even here in Silicon Valley are doing a lot of their collaboration using online tools. Long meetings sitting in conference rooms and reviewing project plans, people don’t do that anymore. With 37signals and some of these tools it doesn’t really matter if the person is in the cube next to you or thousands of miles away.

How do you handle the time difference?

It’s very interesting. Here’s kind of my routine. I wake up about 6:00am. It’s around 10:00pm in China and generally they’re still working. I have maybe a couple of hours overlap with them and then they go offline for eight hours. But then they come back online just about the time that my two-and-a-half-year old goes to bed, around 8:00pm my time, and we can review things together. The really neat thing is, I will go to bed, say, 10 or 11:00pm. I will have shot over some requests or some feedback and they then have seven hours to work on those deliverables, to prepare some things for me to review, so that when I get up and I grab my iPad at 6:00am I have an inbox full of messages.

The beauty of this is we operate 24 hours a day, and we have periods of being online at the same time to collaborate but we also have the benefit of these blocks of time where they can do what they do best without any interruption. During my workday I’m not getting all these emails, getting interrupted all the time. I can focus on the things I need to focus on. Likewise, when they’re cranking away, I’m asleep and I’m not bugging them and disrupting their flow. We each get seven or eight hours in which there’s no interruption. So it works really well.

Do you physically visit the office in China?

Yeah, I pop over there every 12-14 weeks.

Do you feel that face time is necessary for the smooth functioning of the team?

Honestly, I can’t tell you that it’s necessary because, Hugo, my co-founder, is there and it’s his team. He built this team. He manages this team and he has a great relationship with his team. I do believe that companies are built on people. I don’t care how good the technology is. I don’t care how great the market opportunity is. If you don’t have a good culture and a good relationship amongst the team, you will fail. So from a tactical perspective, me being over there isn’t necessary, but from a relational perspective I do believe it’s important that I spend time with them. We’re human beings. We each have our specialties but we have a relationship, and I think when I go over there, we are just strengthening our relationship in a way that you can’t do online via email or Skype.

You speak really highly of the talent in China. Do you think the U.S. should be letting more of these highly skilled people come to our country to work?

I think there are lots of people that are discussing this subject and I defer to their expertise, but we obviously have a problem of a shortage of developers in this country, and so we have a need for a near-term solution and a longer-term solution. Longer term we need to modify our educational system. There are several excellent startups that I think are going to upturn this antiquated, four-year college model and hopefully allow us to help the next generation to build great products. Near-term I do believe that it is in the best interests of our country to modify immigration laws and to allow us to bring in highly talented people to help us build our companies.

What are some of the educational startups that are shaking things up that you’re most excited about?

Obviously there are just the simple tools like Khan Academy. Khan Academy is a great thing, and now there are some games — I think Code Wars — that are specifically designed to help people have fun learning how to write code. One particular startup, New Charter University, comes out of Mitch Kapor’s incubator here in San Francisco.

Any other thoughts on the experience of starting a business remotely?

Just to really overplay the Thomas Friedman topic that the world is flat. We need to move away from this anachronistic way of thinking that there is us versus them. We are a global economy and we now have the tools in front of us to eliminate these geographic boundaries that have traditionally kept companies from growing and building great products. I think at some point in time we won’t just be thinking about country geography but also this whole concept around what does it mean to go to an office every day? This whole concept of driving to a box, sitting in a box all day and driving back is going to change. The way we look at a company is going to move away from being a physical building to being something much more virtualized. I think that this is going to be a growing trend and my kids will look back at it and ask the question: ‘Why weren’t all companies built that way?’

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Crisp notes that for many years most HR departments saw virtual work as the domain of a handful of road warriors who could be relied on to work with their managers to sort out their individual tools and needs. But HR failed to keep up with changing conceptions of virtual work as technology and shifting mindsets allowed the idea of location independence to spread through much larger swathes of organizations. He writes:

As time passed technology made most of us capable of working remotely at least part time with few special arrangements. It also enabled more people to tie into virtual meetings via various types of collaboration programs and online tools. The emphasis shifted away from remote workers as special cases that had to be monitored to an assumption entire teams might be assembled from workers who are located somewhere other than where the leader is or teams in one location being led by a leader located somewhere else.

Or as Wayne Turmel put it in his thoughtful meditation for Management Issues on the themes raised in the Canadian HR Reporter post, “it’s impossible not to acknowledge that while IT was busy building tools (and empires) to cut costs and minimize travel, the discussions frequently didn’t include HR beyond how much they could cut costs (and head count).” He concludes: “As often happens, HR is left to come in after the cow has run off and safe-proof the barn.”

So what questions is HR now scrambling to ask and answer about virtual work? Both Crisp and Turmel have suggestions, such as:

• Are employees expected to be connected 24/7? If so, should they be paid extra for it? And, I’d add, what are the longer-term risks of burnout created by such a policy?
• Are productivity and effectiveness being measured properly when it’s no longer possible to simply drop in on an employee’s cubicle and see what they’re up to?
• Do managers need training in how to communicate effectively at a distance? Issues like the tone of email, handling conflict across distance, making the most of virtual meetings and deciding who to include in which communications come up here, as do questions of how managers can maintain an “open door” policy when they have no door.
• How should managers or HR handle the situation when cliques or subgroups form within virtual teams and information isn’t properly shared?
• How should managers solicit feedback?

What other questions do HR departments have to confront as virtual work becomes more widespread?

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One of the most common definitions of crowdsourcing is “an open call to an undefined group of people.” This definition would seem to exclude a call for input to a more defined and limited group: your employees. Crowdsourcing techniques, however, leverage online technologies to “harness” the input of many and to apply that input toward getting results of some kind, so why can’t they also be applied to the people within an organization instead of without?

Some popular uses of crowdsourcing include:

• Crowd wisdom where many can contribute possible answers to questions.
• Crowd innovation where many can participate in problem-solving.
• Crowd creation where many can be part of producing something and often each participant takes a smaller piece of the whole based on their skills and abilities.
• Crowd voting where the best ideas “bubble” to the top by community review and voting.

Why not take these models and apply them to problem-solving, creative brainstorming, and creation tasks within your organization? You can even use readily available crowdsourcing technology and platforms to facilitate those processes.

Where can you go for crowdsourcing technology? Companies like Chaordix and Spigit specialize in “innovation management,” and they’ve built online tools to manage input from groups and allow for voting and other features to facilitate “crowd” participation. Even a DIY crowdsourcing system such as the one offered by Crowdtap could prove an interesting tool when the “crowd” you use for input and feedback isn’t a large random pool of unknown people but actually the folks working within your own organization.

In organizations, there is a tendency for each team member to operate strictly within their department or division. In virtual teams, these divisions may be less obvious, but the silos still exist, and may even be worsened due to the lack of proximity. By using crowdsourcing tools and applying more democratic methods of soliciting crowd input, allowing for group voting of ideas, and reaching across departments for participation, you may be able to:

• Innovate more quickly because you are tapping into your team in different ways
• Identify issues and reach solutions more effectively by utilizing your team more widely
• Gain insights into your team’s talents and abilities by providing more open opportunities for participation

In some situations, crowdsourcing can take on a competitive edge in the form of a contest or competition where participants are rewarded in some way for the “best” solution — and the best solution is often not something determined by a top-down approach, but rather by the votes of the crowdsourcing community as a whole. We’ve previously written about the gamification of work; in some circumstances, applying a competitive layer to participation in problem-solving or innovation initiatives can increase motivation and stimulate better responses.

Using your team for crowdosurcing can not only help to “get things done,” it can potentially produce fresh, interesting and beneficial results.

Editor’s note: Aliza’s new book, The Complete Idiot’s Guide to Crowdsourcing, has just been published by Alpha.

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1. Run a test project. When you’re just starting out with a virtual team member, try running a test project. Pick something small that isn’t as potentially overwhelming as the big plans you have on the table. That will let you adjust to the situation on a low-risk project.
2. Be available. It may sound obvious, but if your only contact with a virtual staffer is the occasional email, it can be difficult for them to get a complete picture of what’s required.
3. Set up multiple methods of communications. Even if you plan to communicate exclusively through one channel, have other options available. After all, what happens if the internet goes down in your team member’s area and the only way you can get in touch with her is by email?
4. Add more time to your estimates. Lengthening your estimates is a good idea as you can expect to spend more time communicating back and forth if you aren’t sitting next to each other.
5. Record exactly how you do things. Instead of trying to explain what you do and how you do it, try recording yourself in action. With the wide variety of screencasting software available, you can have a video that shows your process in a matter of moments.
6. Provide instructions in multiple formats. The more methods you can employ in getting the message across, the better. If you’re working with multiple virtual team members, it’s likely that they’ll have different learning and communication styles, making it worthwhile to use different formats.
7. Set clear deadlines and expectations. Especially if most of your communication is through email or other written mediums, there are lots of opportunities for miscommunication, so you need to ensure your expactations are communicated clearly
8. Be flexible about how things get done, not what gets done. You can’t afford to be flexible about what gets done: you need certain tasks accomplished. But if your virtual staff has a different process that results in the same end result, don’t let that stress you out.
9. Write an organizational manual. It’s likely that if you’re working with one virtual team member now, you’re going to be working with more in the future. Creating an organizational manual based on your experiences now will make it much easier to handle future projects.
10. Ask your virtual staff for suggestions. Don’t be afraid to give your virtual team members a voice; they may have some helpful hints, especially as if they’re used to working virtually, they may have more experience in the process than you do.

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Distributed Training Technology

With screencasts, webinars and all the other online training tools out there these days, you can address many of the problems that slow down virtual training. For many team members, you may find that the most difficult part of learning a new tool is getting to see it in action, but screen sharing technology (available in many tools, including Skype and join.me) can help here.

Practice Makes Perfect

If you consider how training usually works when everyone necessary to the process is gathered in one place, you may still see some potential problem areas. When it comes to learning a new tool, many organizations follow a similar training pattern. The trainer goes over how to use the tool, following some sort of guidelines that the trainees will have access to. Then the group breaks up, and the trainees have a chance to put what they’ve learned into action, asking questions and helping each other along the way. That group dynamic is difficult to replicate online.

Estimating the Time You Need

There’s no iron-clad rule that states distributed teams needs X more hours of training on a new tool than an in-office team. But because of the nature of a distributed team, it makes sense to budget a little more time for training, even if you’re only making a trainer or an expert available to answer questions when you’re putting training into practice.

There’s no perfect training method that can speed up online training, either. Different team members learn at different speeds. Fortunately, those who push to be allowed to work out of the office on their own may have an incentive to work harder to get a new tool down pat.

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• Immediate recognition. Try to get in the habit of immediately recognizing people when they do good work or provide you with some extra help (Georgina suggested some ways to show recognition and praise here). A quick reply with genuine appreciation for doing a great job is a good place to start, and you can do this over email, instant messaging, phone or with a handwritten note. Be as specific as possible when you thank someone, and include something about why you appreciated their work. Just replying with “Thank you” is nice, but it isn’t very personal and can sometimes seem insincere.
• Set reminders. I know this sounds over the top, but it can help to set a reminder on your calendar every day or once a week to spend just five minutes thinking about your team and their work. This gives you time to reflect on how people are doing and remind you to recognize good work. On the flip side, it also gives you time to think about how you can provide helpful feedback for employees who might not quite be on the right track with a project.
• Staff meetings. I once had a manager who built time into her staff meetings where team members were encouraged to thank other members who had done something particularly awesome that week. This is a good way to make sure recognition isn’t just coming from the manager. Staff meetings are also a great place to provide public recognition or awards for employees, so don’t forget to think about recognition when putting together staff agendas.
• Rewards. Don’t forget to go beyond a simple verbal “thank you” when someone does something truly outstanding. A gift certificate or small bonus in addition to some public recognition are great ways to reward a team or individual for a job well done. For remote employees, make sure that you think carefully about rewards, since even gift certificates for major online retailers, like Amazon.com, can’t always be used in every country. This is where getting to know your team members’ preferences can really help, and giving a gift certificate to a favorite restaurant can be a really personal way to recognize someone.
• Celebrations. Most teams try to get everyone together in person at least occasionally. If you can time those meetings to occur shortly after some big milestone for the team (a big release or deliverable), you can use this valuable in person time to celebrate both team accomplishments and provide individual recognition in person. However, recognition is best when made as close as possible to the work being completed, so don’t withhold recognition until you meet in person.

What are your tips for recognizing remote employees?

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Ask the Big Questions

Last year, I started searching for interns to help manage a temporary project and also to hopefully find longer-term support. I knew, however, that even if the person ultimately did not end up being employed by my company, he or she still needed to walk away with something, and I wanted to make sure that, whatever it was, we achieved that goal by the end of the internship. So I asked them, “What do you want from this internship? What skills and experiences do you hope to acquire?”

Asking those questions gave me the information I needed to structure their internships in a way that ensured we both left the relationship happy, but then I realized there was an even bigger and more important question: “Why do you want to intern here?”

One intern included a detailed cover letter with her application, a story really, that told me what attracted her to my organization and why she thought she was the perfect fit for the internship. I agreed with her, simply because I then knew her story. I knew more about her from that one introduction letter than I did about clients and colleagues I had known for years, and it gave us a wonderful foundation for the relationship.

Learn Their Stories

When I think of the people on my team now, I’m most interested in those who are interesting, and those who are the most interesting are those who have shared their stories.

• What are their dreams and aspirations? As college students, in the interns’ cases, they’re generally starry-eyed dreamers right now, with high hopes for how their lives and careers will turn out, not at all jaded by circumstances and setbacks; they’re not afraid to share those big audacious goals with me. By knowing where they’re going, I can help them get there and, if our goals align, add strength to our shared mission and momentum to that of the company.
• What do they like, and what are their interests? As trivial as it might seem, knowing that one of my interns loves Dr. Seuss, another poetry, and another literature gives me unique insight into who they are as people and a way to appreciate who they are as individuals and, better still, combine our unique talents, gifts, and interests into a company with culture and character.
• What’s their past? By learning a little about where they’ve been and their history, I can learn if they are from a big family, for instance, and perhaps get an idea if they could possibly take on strong leadership roles within the company or if they’ll be good at working as a team.

Relating to Your Team

There are many ways to learn more about the members of your team, but the most important thing is to make the initial effort, using any method that best fits your company and its culture.

• Life lists. One of the tools I’ve been using to get to know my team members is “life lists” (aka “bucket lists,” 100-things-to-do-before-you-die sort of thing). I was originally doing this for myself and as a connecting point for supporters of a project I’m working on, but when one of the interns heard about it, she said enthusiastically, “I’ll do it!,” and within a day had completed hers, too. It’s interesting to see how many things we have in common.
• Stories. “Who are you?,” the caterpillar asked Alice. Get your team to share their stories by writing their own “About” pages for your website, and if you want to encourage greater connectedness, ask them to post them to a common message board or, as Chris Ducker recommended, to a company culture website.
• Company blog. Consider starting a company blog where employees can share funny or inspirational posts. Decide on a format (example, personal or company-related) and set some ground rules (example, no back-biting or negative comments), but then let it grow. You could encourage participation by conducting weekly interviews, where you personally talk with a different person on your team.

As Stephen Covey said, “Seek first to understand, then to be understood.” By learning the stories of the people who make up your team, you’ll be able to relate so much better to each other and be reminded that, at the other end of the Ethernet line, there’s a human being with goals and dreams, quirks and a unique personality, a person you should definitely want to know, because after all, he or she will be helping you build your dreams, too.

How do you better relate to the people on your team?

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As Ducker says, “I don’t think there’s a whole lot of difference between motivating someone from a virtual standpoint and motivating somebody [...] where you’re working in real time with each other under the same roof. It just comes down to simple things, like being a nice guy, being understanding, being flexible, [and] wanting to spend a bit of time with them, above and beyond just giving them tasks.”

Here are a few things Chris recommends to help build stronger relationships with your virtual team:

1. Have an open door policy. “I always make time for my management,” Chris explains, “My management fundamentally run my company for me, and I’m well aware that without them, I would have to come in and start working ridiculous hours every single day. If they need to speak with me, all they have to do is pick up the phone, and I’ll make time to speak with them.”
2. Provide opportunities for career growth. Chris says, “I never want to hire externally, unless I truly have to. I’ll always look internally to try to promote people, if possible. That creates a great culture within a company.”
3. Provide opportunities for education. “I think there [are] other things you can do,” Chris says, “not only spending the time with somebody and giving them career opportunities, but also investing in them. I regularly put my management on different types of courses, training and things like that. It’s developing them as employees, and it gives them the opportunity to better themselves, and they appreciate that.”
4. Provide support resources. “We created our Live2Sell library, which now has just over a hundred books on everything from self-help to how to get over issues and problems in the workplace,” he explains, “People can come up to the HR department and borrow the books, just like in any other library.”
5. Spend time together as a team. “We do one yearly team-building weekend,” Chris says, “where we go out and stay the night at one of the resorts here, and everybody is together.” The purpose of the weekend is to build stronger connections in a fun atmosphere. He adds, “I’ve found that I have a lot in common with [team members]. We enjoy the same things. There is a lot more in common with workmates than a lot of people think.”
6. Treat your team members like family. “We have ten core values, and the first one is, ‘Treat everyone as family.’ That’s really important for any company,” Chris says, “We recently launched our company culture website, Live2Sell Family. It’s open for the public, but it’s all about us, [and] we’re now giving out little mini birthday cakes to everybody on their birthdays.” Another example, he adds, one of his assistants is a big music-lover, and every so often, he emails an iTunes gift certificate, because as Chris says, “The little things make big, big differences.”

“Above and beyond monetary gain,” he adds, “the fact of the matter is that, as long as you give opportunities to people, you’re nice, and they enjoy working for you, they’re not going to go anywhere. As long as you’re treating them well and with respect and paying them what they’re worth, you don’t need to lose people, unless you’re not managing your company properly.” By establishing these little connections, you’ll build better relationships with your virtual team and build a greater sense of unity and purpose.

How do you keep your virtual workforce happy and motivated?

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Here’s a breakdown of some things you should consider before taking a leap into the cloud and trying to bring your team along with you.

1. Portability

How portable is your business? If you’re dealing in intellectual property creation or knowledge work — anything that can be produced and delivered electronically via computers, the Internet and phone — then you’re probably in good shape for moving your company into the cloud. Andy mentioned public relations and marketing as good candidates for virtual companies: the virtual agency model. Any content creation shop with creative teams — ad agencies, news agencies, copywriters, bloggers, podcasters, editors, online producers — can work remotely.

2. Process

Just asking yourself the simple questions: “If we didn’t go into an office together, could we still get work done?” and “If so, how?” These will lead you down the path of thinking about how to configure, or reconfigure, your business. You need to deeply analyze the way you currently get things done and document it. Illustrate your work process using a mind-mapping or flowchart tool. Break down how your projects are handled from start to finish. When does your team meeting face-to-face? Envision how that would look as a videoconference instead. What are the steps you might be eliminating by going virtual? Don’t just stop at mapping out your process and translating that to a virtual workflow. Add dollar amounts to your current process versus a virtual process. You should begin to see why virtual work makes good financial sense.

3. Personality

Even if you’re in an industry with proven virtual models, this doesn’t mean that your company that has been entrenched in “the office” can eschew physical location and hit the cloud running. As you probably know from managing people: people hate change. Even if change is for the best, the very act of changing can paralyze some. You may have to make some hard decisions about how to handle resistance against the change to virtual work. Start with open communications, present the concept of going virtual to your team, and suss out the champions of this model. Chances are, you’ve been approached in the past by someone or several team members who’ve asked about telecommuting, even part-time. For the nay-sayers, find ways to offer support every step of the way as they transition from being in the office to working from home.

You may want to bring in consultants to assess your team and offer individual consulting on setting up their virtual workspaces. Set up training sessions for workers and their managers to make sure everyone is up to speed, not just on the technology changes but the culture changes as well. If not everyone is thrilled with your intention to go virtual, don’t be shocked. Be prepared.

4. Infrastructure

In my post What Does It Take To Run a Virtual Team (Redux), I listed the needs of a virtual team, namely:

• Communications amongst your team members and externally;
• Management of projects, team members, deadlines, and document;
• Archiving of files, knowledge and communications content;
• Interaction between team members including integration, collaboration and socializing.

There is no “one size fits all” technology solution for every company that goes virtual, although there are many enterprise solutions available from Microsoft to Cisco to a never-ending procession of innovative startups looking to solve the problems of virtual work. If you pick a fully-integrated enterprise system, keep in mind it may be more expensive and less flexible than newer, more innovative solutions. The rub of going with smaller startups for your virtual infrastructure needs is that you may have to cobble together several tools, so while they might be highly affordable, you’ll be looking at issues such as cross compatibility and integration.

5. Accountability

A common question managers ask when confronted with the prospect of managing a virtual worker is “how am I going to make sure they get their work done?” A manager who is constantly looking over a worker’s shoulder to make sure they are working is going to have to go through a fundamental shift in how to manage — and how not to manage — to be able to handle managing a virtual team. Managing virtual workers isn’t about watching them like a hawk and micromanaging their every move. Instead, the infrastructure you put into place should have built-in checks and balances to watch productivity and on-time delivery.

Make sure your processes and expectations are not only clear but also communicated clearly to team members. Not everyone will thrive in a virtual work environment, but the issue may be less an inability to get work done and more to do with a feeling of isolation or being disconnected from the team. Be ready to address any issue that crops up as you move toward virtual work and have a plan for addressing issues including missed deadlines, lack of participation, failure to properly document or archive, and forgetting to log time, if that is a requirement.

6. Commitment

You need to decide how committed you are to going virtual and how flexible you’ll be with team members who resist. Can you afford to move in phases, first deploying the team members who are ready, willing and able to take to the cloud, while leaving the others in the office? In order to get the real benefits of going virtual, you should at least consider downsizing the physical work space and look for suitable alternatives that offer real cost savings.

As more and more of your workers opt to go virtual, pretty soon those who are resisting may give in or give up. There is no way to please everyone, but having an understanding that you may have some very unhappy team members from the moment you say “virtual” should help to guide you in your approach. Consider consulting your lawyer to make sure any drastic changes you make in your workplace don’t infringe on workers’ rights.

By thinking through your process carefully and thoughtfully in advance and spending time considering and reviewing the technology you’ll use to build cohesion amongst your dispersed team members, you can certainly construct the ideal virtual workspace. Bringing everyone to the cloud without encountering some digging in of heels is the best scenario, but as a leader and manager, be prepared for the worst.

What do you think about bringing your own company into the cloud?

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Having virtual team members can be a huge asset because you can take advantage of talent regardless of physical location, and you increase the diversity of ideas by having team members who aren’t all living in the same city and having similar experiences. The tricky part is making sure that your remote employees feel like they are an integral part of team and not a second-class citizens. Here are a few ways to make sure that your virtual team members feel loved, instead of neglected:

• Real-time collaboration. Make sure that you have plenty of opportunities for real-time online collaboration for your entire team that allow for virtual members to participate as equals. This replaces the water cooler, hallway discussions and any other quick conversations that you might have by dropping by someone’s desk. The easiest way to do this is to make sure that your whole team is using some kind instant messaging service where they can easily ask questions, share links, work together on projects or just catch up and chat. An even better way to do this is to set up a group chat room or team IRC channel where members can all work together and talk to each other at the same time. By having everyone together in one channel, you don’t need to know who to ask when you have a question, and everyone can keep up with many team conversations whether they are an active participant or just reading the conversation. There are plenty of public tools and public IRC channels that you can use if your team consists of a mix of employees and people outside of the company, but you can also set up instant messaging servers, including group chats based on Jabber / XMPP or internal IRC servers, that live completely inside of the corporate firewall so you can have private company conversations.
• Asynchronous collaboration. Real-time collaboration is great, but not everyone is online 24 hours a day. Email is the classic example of asynchronous communication, and it’s a good way to make sure that everyone on the team receives critical information or updates at the same time. You should also keep in mind that some tasks aren’t going to be as easy to accomplish in email or a text chat. Documentation collaboration, for example, is one of those activities that works better when people can create, edit and update the same version independently regardless of time zone or physical location. You’ll want to make sure that your team has a good document collaboration solution, like a wiki, Google Docs or other tools. This obviously lets your team work together on documentation, but it also gives you a place where you can keep materials that the whole team needs to be able to find. You can store organization charts, contact lists, meeting minutes and materials, presentations and much more. By having everything in a single place where the whole team can find it makes it easier for your virtual team members to easily have access to the same information as your in-person employees.
• Hallway conversations. If you even occasionally work in an office, hallway conversations are just a fact of life. When we see other human beings, we are often reminded of that question we forgot to ask them or in casual conversation some piece of important information creeps up. After you have these informal discussions, think about whether any of the information would be useful for your virtual employees. If so, drop them a quick note to let them know what you talked about and point them to other people that they might want to contact for more information. Just because you have hallway conversations doesn’t mean that your virtual team members can’t also benefit.
• Meetings. Structure your meetings to allow your remote employees to participate as equals. For meetings where some participants are in a conference room, make sure that you send out the agenda and any materials in advance along with a plan for how virtual team members should attend and still be able to hear the discussion. Usually, this means that you need a bridge number where multiple people can call into the line, along with a great speakerphone for the room. During the meetings, remember that the people on the phone can’t see into the room, so you should avoid drawing on the whiteboard or using flip charts, and don’t forget to ask if they have any questions or comments, since you won’t be able to see puzzled looks or body language indicating that they want to add something to the discussion. If the remote employees consistently have a hard time hearing the people in the room, you should consider having everyone call into the meeting from their desk phones. While you lose some face-to-face time for people in the office, you allow everyone to participate equally in the meeting.
• Meet in person. Don’t forget to get together in person at the same location at least occasionally. Take advantage of conferences or large meetings as an excuse to get the whole team together. Having everyone in the same location can help team members get to know each other better and improve their working relationships when working together later online.

How do you make sure that your virtual team members don’t feel neglected?

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Here are some technology and management considerations to take into account when managing a multi-generational virtual team.

Technology

If some team members are young enough to have been around computers most of their lives, it’s reasonable to expect they will be comfortable with the idea of virtual working.

Younger employees are more likely to be comfortable with the technologies that go along with working online, but that may not always hold true. For instance, while a younger team member may be very comfortable with social collaboration tools, she will likely need training when it comes to industry-specific applications.

Management Styles

Younger members of the workforce, especially those in Generation Y, may need more management feedback, and may expect a more collaborative work environment, than their predecessors. While Generation X-ers may have a preference for handling projects on their own, Generation Y members may struggle in a virtual work environment because of the reduced feedback that often happens in such situations.

While the situation is not simply a matter of age — Generation Y-ers are showing similarities to previous generations as they age — you do need to take the age of your team members into account when managing a virtual workforce. You need to make sure that you’re providing a work environment that supports them, whether they need an in-depth support network, as a Millennial might, or whether they want you to cut the interference and get out of their way, as a member of Generation X might.

Beyond Age Differences

The names of different generations, from Millennials to Baby Boomers, are simply shorthand for general trends. Employees of the same generation will never be identical. While you can certainly expect management techniques to change, the most important thing is to keep an eye on individual team members. The best way to minimize the issues that go along with online team collaboration is to pay attention to what’s really going on. You can prepare for certain eventualities by looking at generational trends, but you can’t implement every management technique your team needs until you see the team in action.

That said, it is certainly worth your while to read up on proven techniques for managing the age groups you’re working with. Having specialized tools will let you find the best answers. After all, by working with a virtual team, you have less face-to-face interaction on which to judge situations. Having a few extra techniques is the least you can do to make up for that lack.

How do you bridge the “generation gap” among team members?

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Here’s a short video overview of the service in action:

Managers can setup teams, invite members and assign privileges to allow team members to view each others’ screens. Users can then “clock-in” to activate the monitoring and screen capture service,  and “clock-out” at any time to pause it.

Personally, I’m uncomfortable with the premise of Peerdrum; the need to resort to this type of tool strikes me as illustrating a failure of management and a breakdown of the trust between employers and workers. Peerdrum appears to be based on a corrective philosophy; it assumes that workers left to their own devices will drift from their objectives.

Most information workers multitask and flit from project to project, and creative disciplines often require a level of play and exploration that is not well represented by a series of screenshots — if anything it could distort and damage perceptions.

Fundamentally, if the output of a worker is sound, is this type of tracking really necessary? Rather than a slideshow of screenshots, I think perhaps an open multi-person video channel could help to keep a team pulling together much more comfortably. Experiencing a coworker’s body language, demeanor and conversation will reveal much more than the visible content of their desktop.

Last year, we published a guest post covering some best practices for remote monitoring of workers by the CEO of RescueTime, which emphasized using monitoring tools to enhance productivity, rather than for employee surveillance; Peerdrum appears to be primarily a surveillance tool.

If you’re interested in the topic of how to manage remote workers effectively, it’s something we’ll be exploring in depth  at our Net:Work conference, coming to San Francisco in December.

Do you think surveillance tools like Peerdrum are necessary in modern workplaces?

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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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The dashboard has details of all your current projects. Every project consists of messages (discussion forum), lists (tasks), pages (wiki), people (contacts on the project) and chat. In less than 10 minutes, I created two projects and added content for each.

Teambox feels easier and more intuitive than Basecamp. Not once did I need to peek at the help file or the Textile (text formatting) reference; the tips on the page were enough. Even after using Basecamp for a while, I still needed to look up its Textile reference.

Basecamp’s interface is nicer than Teambox’s, though; it’s sleeker and more eye-pleasing, with a dash of color. By contrast, Teambox’s interface contains little color and it doesn’t look the same in all browsers. For example, it uses a serif font in Google Chrome, making it a harder read than the sans-serif font displayed in Firefox. The project dashboard formatting could stand some improvement, too.

Web workers, especially those working solo, might prefer Teambox just because it’s free. You can freely create a project for every client and add those clients to the projects. However, if you need to build a complete extranet, complete with branding (which you have to pay for with Teambox), Basecamp is still the collaboration tool of choice. Furthermore, Basecamp has been around longer and has third party apps that work it. I’m sure Teambox will add new features as it develops a following and continues to grow.

You need to determine your own needs and chose the applications that best meets those needs. For a freelancer like me, Teambox fits my bill if I need to collaborate and manage projects with clients.

What team collaboration app do you use?

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Here are some needs virtual teams face daily:

Here is a diagram of what we’re currently using as our solutions and which issues and needs each solution addresses. The software we currently use is in orange. Yellow designates the software we are considering.

Where do we go from here?

It seems that Socialtext and GoToMeeting are the next solutions we should integrate. However, how many more SaaS products will we need to cobble together with our current infrastructure in order to meet immediate and upcoming needs as our team continues to grow? I think it’s better to go with solutions that can meet multiple technology needs. When each solution we adopt only tackles one or two functions, there seems to be no way to avoid a technology patchwork quilt. Is there even a system out there — that we just don’t know about — that can provide us with a completely integrated solution. And if so, can we afford it?

In my mind, adding Socialtext and GoToMeeting will certainly meet some immediate needs, but integrating it will take two things that go beyond me simply adopting and paying for the services:

1. We’ll need to define how the new software fits into our overall process and multiple solutions;
2. We need to somehow encourage adoption from the team.

The latter is a key problem. With all of these disparate solutions brought together to make up our tech infrastructure, we are all suffering information overload. Learning and adopting yet another app seems unbearable.

Next on our plate is a virtual PBX system that can accommodate international team members or at least some stitched together work-around to keep a PBX system affordable for a far-flung team.

What systems and software do you have in place to run your virtual team? What other issues are you facing where you still haven’t found an appropriate solution?

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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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